Hildebrand v R (No. 2)

Catchwords: SENTENCING — appeal against sentence — where appeal is out of time
BIAS — whether an apprehension of bias arises from comments made by the sentencing judge
PROCEDURAL UNFAIRNESS — whether it was procedurally unfair for the sentencing judge to reject a diagnosis that was unchallenged
NEW EVIDENCE — whether the applicant can rely on new reports prepared for use in sentencing proceedings in the District Court — whether the District Court sentencing judge will be bound by the findings of the sentencing judge in these proceedings — appeal dismissed

Legislation Cited: Crimes Act 1900 (NSW)
Crimes Act 1914 (Cth)
Criminal Appeal Act 1912 (NSW)
Crimes (Sentencing Procedure) Act 1999 (NSW)
Supreme Court (Criminal Appeal) Rules 2021 (NSW)

Cases Cited: Baladjam v R [2018] NSWCCA 304; (2018) 341 FLR 162
Barnes v R [2022] NSWCCA 140
Betts v The Queen (2016) 258 CLR 420; [2016] HCA 25
Col v R [2022] NSWCCA 279
Concrete Pty Ltd v Parramatta Design & Developments Pty Ltd (2006) 229 CLR 577; [2006] HCA 55
Crackin’ Snack Pty Ltd v Gameking Australia Pty Ltd [2024] NSWCA 182
Ebner v Official Trustee in Bankruptcy (2000) 205 CLR 337; [2000] HCA 63
GAR v R [2021] NSWCCA 265
Goodridge v R [2014] NSWCCA 37
Heath v R [2016] NSWCCA 24
Hildebrand v R [2021] NSWCCA 9
Kentwell v R (No. 2) [2015] NSWCCA 96
Kentwell v The Queen (2014) 252 CLR 601; [2014] HCA 37
Khoury v R [2011] NSWCCA 118; 209 A Crim R 509
Lawavou v R [2025] NSWCCA 35
Lee v Huo [2026] NSWCA 15
Lehn v The Queen (2016) 93 NSWLR 205
Michael Wilson & Partners Ltd v Nicholls (2011) 244 CLR 427; [2011] HCA 48
O’Neal-Show v R [2010] NSWCCA 42
R v Birks (1990) 19 NSWLR 677
R v Fordham (1997) 98 A Crim R 359
Rouvinetis v Knoll [2013] NSWCA 24
Smith v R [2024] NSWCCA 59
Tarrant v R [2018] NSWCCA 21
Tran v R [2014] NSWCCA 32
Webb & Hay v R (1994) 181 CLR 41; [1994] HCA 30
Zreika v R [2012] NSWCCA 44; (2012) 223 A Crim R 460

Category: Principal judgment

Parties: Vaughan Mark Hildebrand (Applicant)
The Crown (Respondent)

Representation: Counsel:
V Hildebrand (Applicant, self-represented)
F Sullivan (Respondent)
Solicitors:
V Hildebrand (Applicant, self-represented)
Solicitor for Public Prosecutions (Respondent)

File Number(s): 2017/00164080

Publication restriction: Nil

HEADNOTE

[This headnote is not to be read as part of the judgment]

The applicant, Vaughan Mark Hildebrand, was convicted after pleading guilty to 26 charges (with 18 additional matters being taken into account). The applicant was originally sentenced on 27 September 2019.

The applicant appealed the original sentence to this Court, and one appeal ground, which asserted error by the sentencing judge having taken into account certain Commonwealth charges on a Form 1 attached to charges brought for NSW offences, was upheld. The remainder of the appeal grounds were dismissed. The same sentencing judge conducted the resentencing hearing, and it is that sentence that is the subject of this appeal.

The applicant filed an application for an extension of time to give notice of intention to appeal.

There are four grounds of appeal:

1. Procedural unfairness;
2. Apprehension of bias;
3. Error of fact with respect to remarks made as to the impact of COVID-19 on the applicant’s conditions in custody; and
4. New/fresh evidence with respect to the new reports of Dr Pusey and Dr Furst.

The Court held (Coleman J, Kirk JA and Sweeney J agreeing) granting the extension of time, granting leave to appeal the sentence, and dismissing the appeal:

1. Due to the applicant’s circumstances and difficulties faced in prison, including inability to secure legal representation and difficulties conducting research, leave was granted to file the notice of appeal out of time: [7]-[9].
2. An apprehension of bias did not arise as the sentencing judge did invite additional submissions, but made it clear that absent such submissions, her Honour was likely to make the same findings as in the first sentencing judgment: [55], [61].
3. Given that the applicant made no submissions in the resentence hearing raising the diagnosis of unspecified paraphilic disorder, and in circumstances where her Honour had made it plain that absent further material and submissions, she was unlikely to make any different findings that she did in the first sentence judgment, there was no procedural unfairness. The applicant’s legal representatives were aware of her Honour’s views on the diagnosis from the first sentence judgment and was alert to the possibility that she may reject it: [90]-[94].
4. The reference to COVID-19 by the sentencing judge in the remarks on sentence was plainly a slip. No submissions were made by the applicant’s legal representatives regarding COVID-19 restrictions making the applicant’s time in custody more onerous, and the applicant had not established that if this consideration had been taken into account, it would have reduced the sentence imposed such as to render a serious injustice or cause a miscarriage of justice: [103]-[105].
5. The applicant could not rely on new evidence. Neither of the two new expert reports casts any new light or offers any new conclusions on the circumstances giving rise to the offending, and it cannot be concluded that the absence of this material resulted in a miscarriage of justice because the reports would have had a real bearing on the exercise of the sentencing discretion: [118].
6. The sentencing judge’s findings with respect to the inapplicability of the diagnosis of unspecified paraphilic disorder to the facts as her Honour found them is a finding of fact that does not bind a District Court judge in a subsequent sentence hearing: [120].

JUDGMENT

1. KIRK JA: I agree with Coleman J.

2. SWEENEY J: I agree with Coleman J.

3. COLEMAN J: Vaughan Mark Hildebrand (the applicant) seeks leave pursuant to s 5(1)(c) of the Criminal Appeal Act 1912 (NSW) to appeal against the sentence imposed on him by Tupman DCJ (the sentencing judge) in the District Court on 10 February 2022. The applicant was sentenced for multiple Commonwealth and New South Wales offences. He received an effective term of imprisonment of 20 years, commencing on 31 May 2017 expiring 30 May 2037. A non-parole period of 15 years was fixed, meaning that the first date that the applicant is eligible for release to parole is 30 May 2032.

4. The applicant was self-represented on the appeal. A Notice of Intention to Appeal was filed on 11 February 2022. The Notice of Appeal was filed on 27 October 2025. The appeal is out of time. The applicant requires leave to extend the time to file the Notice of Appeal: r 3.5(5) Supreme Court (Criminal Appeal) Rules 2021 (NSW).

5. For the reasons below, I would extend the time for the applicant to file the Notice of Appeal, grant leave to appeal against sentence, but dismiss the appeal.

Extension of Time

6. The Court has a discretion to extend the time for the filing of a Notice of Appeal. Whether an extension is granted is to be determined by the interests of justice in the particular case: Kentwell v The Queen (2014) 252 CLR 601; [2014] HCA 37 (Kentwell) at [32]. In exercising this discretion, the Court should have regard to the prospects of success of the appeal, addressed by reference to s 6(3) of the Criminal Appeal Act 1912 (NSW): Kentwell at [33]-[34], as well as the explanation given for the delay: Baladjam v R [2018] NSWCCA 304; (2018) 341 FLR 162 at [93].

7. The applicant filed an application for an extension of time to give notice of intention to appeal. In it, he says he was unable to secure legal representation after Legal Aid denied him funding. He had appealed the denial but was unsuccessful. The applicant also said he had contacted the New South Wales Bar Association and the Law Society of New South Wales for pro bono assistance to no avail.

8. The applicant also spoke of the difficulties he faced whilst incarcerated, particularly in conducting research and having material printed. The applicant remains self-represented.

9. In the interest of finality, I propose to grant leave for the applicant to file the Notice of Appeal out of time.

Procedural Background

10. The applicant was originally sentenced by the sentencing judge for the same offences on 27 September 2019 (the first sentence judgment). He had pleaded guilty to the 26 charges brought against him (with 18 additional matters being taken into account on 10 separate additional offence documents under s 33 of the Crimes (Sentencing Procedure) Act 1999 (NSW) and s 16BA of the Crimes Act 1914 (Cth)). He appealed to this Court. That appeal was heard on 7 October 2020 with the decision being handed down on 15 February 2021 (Hildebrand v R [2021] NSWCCA 9) (the first appeal).

11. In the first appeal there were 6 grounds of appeal. They included grounds going to accumulation of the sentences imposed, error in the sentencing judge’s assessment of the objective gravity of the offending, and manifest excess of the sentence imposed. One ground, which asserted error by the sentencing judge having taken into account certain Commonwealth charges on a Form 1 attached to charges brought for NSW offences, was upheld. The Crown had identified this issue in its written submissions on that appeal. This led to an amended ground 3. The Crown effectively conceded error and the appeal on this ground was allowed. All the remaining grounds were dismissed. The sentences were quashed and the matter was remitted to the District Court for resentencing. The same sentencing judge conducted the resentencing. It is the sentence imposed by her Honour following the resentencing hearing that is the subject of this appeal.

The Offending

12. The first sentence judgment set out in detail the facts of the offending. In the first appeal, Davies J summarised the offending from [43]-[215]. The number of charges and nature of the offending conduct led to each the first sentence judgment and the judgment of this Court on the first appeal being lengthy. There was no challenge to any of the factual findings which detailed the offending either in the first appeal, nor in this appeal. The nature of the grounds of appeal raised on this appeal do not require a detailed analysis of the facts of the offending. I therefore do not intend to repeat the details of the offending except in so far as it is relevant to a ground of appeal.

13. In summary, the offending involved the applicant attempting to blackmail young women known to him to provide explicit photographs of themselves to him, or provide sexual favours, under the threat of intimate images being disseminated if his demands were not met. The applicant created several false online identities, and in some cases, the victims did not know that he was using these false identities and confided in him about the demands they had received online from those false identities. In fact, the demands were coming from the applicant.

14. The offending took place between 2007 and 2016. The applicant was aged between 19 and 28 years during his offending. He was a serving NSW police officer from December 2011.

The Remarks on Sentence (ROS)

15. The sentencing judge annexed and incorporated by reference into the ROS the first sentence judgment. This included her Honour’s summaries of the charges to which the applicant had pleaded guilty, the facts of the offending and her findings on sentence, including as to the objective seriousness of the offending.

16. Three Commonwealth sequences, being sequences 25, 36 and 52 had been wrongly attached to New South Wales charges using the Form 1 procedure. The resentence involved a consideration of the impact on the overall sentence with those Commonwealth matters now being taken into account under s 16BA of the Crimes Act 1914 (Cth) for other Commonwealth offences to which the applicant had pleaded guilty.

17. After reviewing the procedural history of the matter, her Honour referred to the judgments in this Court from the first appeal. Her Honour referred to [244] of the judgment of Davies J, where his Honour said:

Although it will be necessary for sequences 25, 36 and 52 to be attached to [C]ommonwealth offences at any resentencing, it is not likely that the overall sentencing of the applicant will be significantly affected. For that reason, it is appropriate for this Court to consider the remaining grounds of appeal to minimise the risk of any further appeal once the resentence exercise is complete.

18. The sentencing judge then noted that all remaining grounds of appeal in the first appeal were dismissed.

19. The sentencing judge also referred to passages from the judgment of Garling J in the first appeal. Her Honour referred to [275] and [279] of Garling J’s judgment where his Honour said of the first sentence judgment:

In the complex and most difficult sentence judgment with which Tupman DCJ was confronted, as the judgment of Davies J clearly shows, the applicant has no, and could not have any, grounds for any successful complaint about the sentences which were actually imposed. That is except for the error of law, dealing with whether three commonwealth offences could be taken into account by the sentencing judge, using the New South Wales Form 1 procedure, when imposing sentences for New South Wales offences.

Having regard to the complexity of the sentences which were imposed, the way in which the sentencing judge aggregated some but not all of the sentences, and the way in which her Honour assessed concurrency and in particular the totality of the applicant’s criminality, I very much doubt whether the overall effect of the sentence which the applicant is obliged to serve - 20 years with a non-parole period of 15 years will be in any way altered when he comes to be resentenced…

20. The sentencing judge then said in the ROS:

I can but concur.

Whilst these comments by Davies JA and Garling JA about the appropriateness of the ultimate overall sentence are largely obiter, nonetheless they remain persuasive, especially in relation to an assessment of the overall criminality represented by all offending. Exactly the same 26 substantive and additional offences are before on resentence…

The material tendered by the Crown on this resentence is no different to that originally before me for sentence, except to the extent necessary to reorder and rectify the errors in relation to the Form 1 and s 16BA documents. There has been some additional evidence tendered in court on behalf of the offender. That includes a psychological report, dated 1 August 2021 of Dr Pusey. The offender retendered the psychiatric report of Dr Furst, dated 30 June 2019. There are also two letters written to the Court by the offender, one dated 6 June 2021 and the other 3 August 2021 and the offender also gave evidence on this resentence.

I do not accept that this material indicates any real change in the offender’s circumstances…

21. The sentencing judge accepted the Crown’s submission that Dr Paul Pusey’s (Dr Pusey) diagnosis of post-traumatic stress disorder and substance abuse disorder had already been diagnosed by Dr Richard Furst (Dr Furst) and was taken into account on the first sentence. She said that there was nothing new in Dr Pusey’s report in relation to those two issues.

22. Further, her Honour held that the issue of alleged childhood sexual abuse was disclosed by the offender to Dr Furst and addressed by him as having no real connection with the offending behaviour such as to reduce the offender’s moral culpability. She accepted the Crown’s submissions that notwithstanding Dr Pusey’s more recent report, there was nothing in the evidence which would support a finding that any child sexual abuse suffered by the applicant had any relevant connection to the offending.

23. The sentencing judge “specifically reject[ed]” Dr Pusey’s opinion that what she had in the first sentence judgment described as “clearly manipulative and cunning behaviour” on part of the applicant “[m]ay in fact reflect an incoherence in relation to his view of self which impair[ed] his consequential thinking as well as his functional capacity within his interpersonal domain of functioning”. She said that if Dr Pusey’s opinion was that the offending may have “amounted to incoherent behaviour and impaired reasoning about consequences, caused at least in part by childhood sexual abuse”, there was nothing in the facts surrounding each of the offences to support that opinion.

24. Her Honour said:

Overall, it is my view that there is nothing in the additional evidence called on behalf of the offender on resentence which amounts to any relevant change of circumstances to those which were before me originally. Those were taken into account for that sentence, including an acceptance that he would serve his term of imprisonment in somewhat more onerous circumstances because of the nature of the offending, his previous employment as a police officer and the impact of Covid related restrictions in the present system, also the impact of his mental health and diagnosed conditions and the extent to which that affected the assessment of general deterrence and an assessment of his prospects of rehabilitation and his expressions of remorse and contrition. In my view, there is nothing which amounts to any real change in circumstances from the evidence now before me on resentence and I make no different or additional findings in relation to those matters.

25. Her Honour rejected the submission that any delay in the resentence of the offender, if established, impacted the appropriate sentence and any non-parole period. The sentencing judge did not accept that there had been any additional significant impact on the applicant within the prison system following the Court of Criminal Appeal decision when he was effectively treated again as a remand prisoner rather than as a sentenced prisoner.

26. A submission was made by counsel for the applicant on resentence that the sentencing judge might revisit the finding of special circumstances to increase the parole period to be served by the applicant. That submission was said to be based upon a consideration of his mental health, the conditions of his incarceration, and the fact of the accumulation of sentences. The sentencing judge rejected these submissions. Her Honour said that these matters had all been considered in the original sentence and, specifically with respect to the accumulation of sentences, was raised and rejected in the Court of Criminal Appeal. Her Honour said nothing tendered by the applicant on resentence, nor any submissions made on his behalf, caused her to alter any of the findings made in the first sentence judgment.

27. Her Honour said:

In those circumstances, and bearing in mind the fact that the Court of Criminal Appeal has effectively endorsed all of the earlier findings in relation to objective criminality and indicative sentences imposed… taking into account the total criminality and the fact that exactly the same offences are now before me for resentence as were before me on the last occasion, I will not be altering any of the sentences not impacted by any of the impugned Commonwealth additional offences.

28. Her Honour said that this meant that the only sentences which needed to be revisited and considered were those for sequences 55, 37 and 27 (being the State offences in relation to which the Commonwealth offences were impermissibly taken into account), and sequences 18 and 30 (being the Commonwealth offences which now had the additional Commonwealth offences to be taken into account). Her Honour then went on to consider each of those sequences and impose sentences for them. I do not consider it necessary to set out the detail of her Honour’s discussion with respect to those sequences as there is no complaint in any of the grounds of appeal with respect to how she did so, nor the length or structure of the sentences she imposed.

29. As observed, the effective overall sentence imposed was one of 20 years imprisonment with a non-parole period of 15 years.

Additional material on appeal

30. The applicant sought to read two documents styled as “affidavits” dated 23 August 2025 and 7 September 2025. I say these documents were styled as affidavits because they have simply been signed by the applicant and not attested before an appropriate person. Nevertheless, as the applicant was self-represented, they were received, with [11]-[14] of the document dated 7 September 2025 being treated as submissions only. It was read on the usual basis.

31. The “affidavit” dated 23 August 2025 attached a new psychological report of Dr Pusey dated 24 January 2025, and a new psychiatric report of Dr Furst dated 2 May 2025. The reports are new or fresh evidence and are related to ground 4 which is discussed below. The applicant did seek to suggest that some of the reports were relevant to ground 1 (being a denial of procedural fairness). [1] I will deal with the use of those reports, or parts of them, in support of that ground below.

32. The Crown read an affidavit of Steven Thomson sworn 20 October 2025 on the usual basis. It annexed documents relevant to the applicant’s time in custody, including records of assaults on him and an updated custodial record.

Grounds of appeal

33. There are four grounds of appeal:

34. Procedural unfairness;

35. Apprehension of bias;

36. Error of fact – with respect to remarks made as to the impact of COVID-19 on the applicant’s conditions in custody; and

37. New/fresh evidence – being new reports of Dr Pusey dated 24 January 2025, and Dr Furst dated 2 May 2025.

Ground 2 – Apprehension of Bias

34. It is appropriate to deal with this ground first. In Lee v H**uo [2026] NSWCA 15 (Lee v Huo), the Court of Appeal was dealing with an appeal raising, amongst other grounds, an allegation of apprehended bias. At [52] Bell CJ, with whom Mitchelmore and Stern JJA agreed, referred to Concrete Pty Ltd v Parramatta Design & Deve**lopments Pty Ltd (2006) 229 CLR 577; [2006] HCA 55. There, Kirby and Crennan JJ, with whom Gummow ACJ agreed at [3] said, at [117]:

An intermediate appellate court dealing with allegations of apprehended bias, coupled with other discrete grounds of appeal must deal with the issue of bias first. It must do this because, logically, it comes first. Actual or apprehended bias strike at the validity and acceptability of the trial and its outcome. It is for that reason that such questions should be dealt with before other, substantive, issues are decided.

35. In Lee v Huo, because the ground raising bias was formulated in a composite fashion drawing on other grounds of appeal taken together and other supplementary arguments, it was expedient, “exceptionally”, to deal with those other grounds first (Bell CJ at [53]). In this appeal, the ground of bias stands alone. Whilst the ground of a denial of procedural fairness, if established, may also strike at the validity and acceptability of the trial and its outcome, that is not always the case (see Smith v R [2024] NSWCCA 59 and the authorities discussed by Basten AJA at [42]-[44]). In accordance with authority, and the logic of doing so referred to, Ground 2 should therefore be dealt with first.

Legal Principles for apprehended bias

36. The test for determining an allegation of apprehension of bias is well known. It is whether a fair-minded person might reasonably apprehend or suspect that the judge might not bring an open and impartial mind to the resolution of the issues: Webb & Hay v R (1994) 181 CLR 41; [1994] HCA 30 per Mason CJ and McHugh J at [47]; Ebner v Official Trustee in Bankruptcy (2000) 205 CLR 337; [2000] HCA 63 at [6].

37. In Tarrant v R [2018] NSWCCA 21 the Court (Basten JA, R A Hulme J and Hidden AJ) said at [9]:

There was no issue in this Court that, where actual bias is not alleged, the legal test, as expressed in Johnson v Johnson, requires the court to be satisfied that “a fair-minded lay observer might reasonably apprehend that the judge might not bring an impartial and unprejudiced mind to the resolution of the question the judge is required to decide.” The High Court has reaffirmed the salience of the test on subsequent occasions, including in Michael Wilson & Partners Ltd v Nicholls. The so-called “double might” test is by no means easy to apply: its application requires attention to four discrete elements.

(1) First, there is the postulate of the “fair-minded lay observer”. Use of that expression reflects the principle that it is public confidence in the administration of justice which is sought to be preserved and not, as explained in Johnson v Johnson, “the assessment by some judges of the capacity or performance of their colleagues.”

(2) Secondly, the test has been described as “objective”, by which is meant a third party’s assessment of the judge’s conduct and capacity, and not, as with actual bias, an assessment of the judge’s own state of mind.

(3) Thirdly, there is said to be a two-stage process required; it is necessary to articulate “the connection between the events giving rise to the apprehension of bias through prejudgment and the possibility of departure from impartial decision-making.”

(4) Fourthly, use of the term “might” lowers the burden of proof below that of probabilities. Thus the court need not be satisfied that the fair-minded lay observer “would” have such an apprehension; nor need any apprehension in the mind of the observer itself involve a state of satisfaction on the probabilities.

38. The applicant in his written submissions, also referred to the passage from Tarrant which referred to Rouvinetis v Knoll [2013] NSWCA 24 where at [24] Basten JA said:

The court must thus accept that a fair-minded lay observer will not necessarily have the same confidence as do judicial officers in the ability of their colleagues to maintain objective impartiality.

39. The applicant confirmed in the hearing that he was asserting an apprehension of bias, not that the sentencing judge was actually biased. [2]

Applicant’s submissions

40. The applicant relied on comments made by the sentencing judge at a directions hearing on 31 May 2021 and the sentence hearing on 16 August 2021. He also said he was relying on the ROS to support his argument that there was a reasonable apprehension of bias on her Honour’s part.

41. The applicant focused on several parts of the transcript containing comments made by the sentencing judge during the directions hearing on 31 May 2021 to schedule the resentence hearing. Those extracts show, he said, that her Honour was critical of the Court of Criminal Appeal. These parts of the transcript reflect comments made by her Honour that the Court of Criminal Appeal, after determining that there had been error, could have resentenced the applicant rather than remitting the matter back to her Honour. The applicant referred to several passages of the transcript which he says reflected a criticism by her Honour of the Court of Criminal Appeal which indicated a displeasure at her having to resentence the applicant. These comments include the following:

42. On 31 May 2021 at the directions hearing, her Honour said:

Can I say at the outset, I have no idea, with the greatest of respect to the Court of Criminal Appeal, why they couldn’t have just done this themselves and I have made that comment to Garling J, who spoke to me about it not long after the decision. It seems to me to be a straightforward sort of issue that, with the greatest of respect, did not require the quashing of all of the sentences. However, that’s a situation that we have found ourselves in. When I was asked for a convenient or suitable date, my answer to it was, well, it depends what I have to do.

2. Her Honour also said:

…In fact, with the greatest of respect, if you actually look at the decision of the Court of Criminal Appeal, it’s nowhere near straightforward and there was possibly another argument available in fact. But nonetheless, they’ve done what they’ve done and then they have not gone on and done what, with respect, they should have done thereafter…

42. In addition to those matters which the applicant submits show her Honour being unhappy with the task at hand, the applicant referred to other comments of the sentencing judge at the directions hearing which, he submits, were indicative of her failing to approach the resentencing exercise afresh. These included her Honour saying:

How much less, if any, should he get for not having those form 1s taken into account on the state offences and how much more should he get on the [C]ommonwealth offences for having extra sentence taken into account? That’s what it’s all about, isn’t it?

43. The applicant submits that this comment by the sentencing judge denied him “the fundamental right of the resentencing exercise, that is for her Honour to start the sentencing process afresh. Whilst the Court of Criminal Appeal quashed the sentence imposed… due to a form one error, her Honour subsequently narrowed the field of the resentencing to only the form 1 errors…” (Applicant’s Written Submissions (AWS), p 4).

44. The applicant referred to an additional passage at the directions hearing being an exchange between the then Counsel for the applicant and the Bench:

BETTS: The basis to resentence, is there any room for me to go back and ask your Honour to consider special circumstances and rehabilitation?

HER HONOUR: You could try.

BETTS: I would raise that with your Honour.

HER HONOUR: I would have thought in the circumstances of an otherwise unsuccessful appeal to the Court of Criminal Appeal, whereas I don’t recall that being raised as a ground of appeal, and all of the grounds of appeal that were raised by the accused were dismissed by the Court of Criminal Appeal and the only appeal that was upheld was one that was raised in fact by the DPP.

BETTS: So, basically your Honour is saying no?

HER HONOUR: I am not saying no because this is a resentence. But what I am saying is that it would be an unusual circumstance in the absence of any other evidence there to be any finding that was any different. But I don’t know.

BETTS: There were just three areas that I wondered if I may raise with your Honour at the time, but they are very short.

HER HONOUR: You would have every right to do so because this is a resentence.

45. The applicant submits that having regard to the test for apprehension of bias and that his Counsel had to clarify whether she could make further submissions, “it stands to reason a lay observer could conceive her Honour had a prejudged mind” (AWS p 5).

46. The applicant also referred to the following passages in the same vein. The italicised part of the passage was not included in the applicant’s reference:

HER HONOUR: Can I just say again - and this is perhaps just a first thought - that as a first thought, in the absence of any further submissions and, particularly, as this has been a largely unsuccessful appeal on merit in the Court of Criminal Appeal on behalf of the accused, I would be unlikely to make any different findings in relation to objective criminality and accept for those to which there might be either fewer or more form one offences attaching, be unlikely to make any different findings about what the sentence length ought be. I don’t know. But again, those individual components are not really the issue on that sentence because it really had to do with what the final figure was on a totality basis.

… (Discussion as to dates and the time required)

HER HONOUR: …If this were being resentenced in the Supreme Court, I would get a whole week out-of-court to deal with this and then a whole week to deal with the outcome.

BETTS: What would be the most convenient for your Honour?

HER HONOUR: The Court of Criminal Appeal could do what it should have done in the first place and resentence them as they could easily have done.

BETTS: Unfortunately, that’s gone.

HER HONOUR: On the basis that this was an overwhelmingly unsuccessful defence appeal except for the one legal ground that was raised by the Crown that has, with the greatest of respect, on the evidence that was then before the Court of Criminal Appeal, almost no difference to the outcome, particularly so when one of the judges said this seemed like about the right outcome to me, in fact on the basis it might have been a bit too lenient.

47. The sentencing hearing took place on 16 August 2021. [3] Dr Furst’s report of 30 January 2019 was again tendered. A report of Dr Pusey of 1 August 2021 was also tendered, as were two letters from the applicant. The applicant gave evidence at the sentence hearing and was cross-examined.

48. Towards the end of the sentencing hearing, her Honour said:

HER HONOUR: They are the submissions that each of you want to make then. My task now is to decide how to deliver this judgment because I can assure you, both of you, that I have absolutely no intention of re-writing the 90-page judgment. I don’t know whether any of you have given any thought to how it is that this judgment should be delivered.

49. The applicant refers to the italicised portion of that quote as additional evidence of the apprehension of the sentencing judge’s bias. The applicant submits that the conduct of the sentencing judge, and the comments that I have referred to, reflected the fact that she simply imposed the same sentence as in the first sentence proceedings when the first sentence had been quashed by the Court of Criminal Appeal. This, he submitted, manifested the apprehension of bias. He submitted that the sentencing judge came into the resentence hearing thinking her previous sentence had been “endorsed” by the Court of Criminal Appeal and had a prejudged mind and did not sentence him afresh. This was regardless of the additional material in the second sentence proceedings.

The Crown’s submissions

50. The Crown accepted in the Crown Written Submissions (CWS) at [60] that the sentencing judge “expressed that her preference would have been for the Court of Criminal Appeal to resentence the applicant”, however, at no stage did she express a view that she was not open to further submissions, or the possibility of revisiting any previous findings. Rather, the Crown submitted that the sentencing judge made it clear that the applicant was to be resentenced afresh and expressly invited further submissions. The Crown referred to the passage I have extracted at [44] above emphasising the last comment of her Honour. The Crown noted that in the passage extracted at [46] above, her Honour expressly referred to her “first thought, in the absence of any further submissions…”.

51. The Crown submitted that it was clear from the exchanges referred to by the applicant that the sentencing judge had invited further submissions from each party if the legal representatives were of the view that such submissions should be made. Her Honour indicated that it was unlikely she was to make different findings in the absence of any other evidence. The Crown noted that the parties did not submit that her Honour should make any different findings with respect to objective seriousness, and the submissions made by the applicant’s counsel and the second sentence hearing were confined in nature. The Crown submits that her Honour made it clear that further submissions could be made and fairly forecasted that if they were not, it was likely that her previous findings would be adopted.

52. The Crown submitted that the additional evidence tendered by the defence was dealt with by her Honour in the ROS. In those passages her Honour made findings, recited at [20] above, that she did not consider that the additional evidence tendered by the applicant on resentence caused her to change her findings made on the first sentence.

53. The Crown submits that there is nothing in her Honour’s conduct, or in the ROS, which would indicate any apprehension of bias.

Determination

54. I agree with the Crown submissions.

55. I consider that it is clear from a reading of the whole of the transcripts of the directions hearing and the sentence hearing that the sentencing judge did invite additional submissions, but made it clear that absent such submissions, she was likely to make the same findings as in the first sentence judgment. Read fairly, although expressed in what could perhaps be considered robust language, her Honour’s comments should be considered her tentative views on the findings she would likely make absent further submissions (see Concrete Pty Ltd v Parramatta Design & Developments Pty Ltd (2006) 229 CLR 577; [2006] HCA 55 at [112]). These views were mostly expressed in the directions hearing to set the matter down for resentence.

56. The italicised parts of the passage extracted by the applicant referred to at [48] above do not reflect the full exchange between the applicant’s counsel and her Honour. It is important to assess the passages relied upon by the applicant in the full context of the transcripts and remarks rather than cherry pick parts of them: Crackin’ Snack Pty Ltd v Gameking Australia Pty Ltd [2024] NSWCA 182 at [85] and [92]. The exchange occurred at the conclusion of submissions from each of the parties, including by the applicant’s counsel. The applicant’s counsel had provided written submissions on resentence which did not cavil with her Honour’s finding in relation to objective seriousness in the first sentence judgment. The applicant’s counsel noted that she only raised four issues – being subjective matters. They included hardship in custody, special circumstances and delay.

57. As to delay, it was explained by counsel for the applicant that the issue was really the fact that the applicant had to go back into remand and his uncertainty about what was happening in relation to that. She submitted that if there is a delay where there is uncertainty, the court may take that into account. Her Honour then said:

HER HONOUR: I would have thought that it was perhaps less of an issue with a person who has already been sentenced and in relation to whom the Court of Criminal Appeal has said, if I can paraphrase it, we see nothing wrong with the ultimate sentence that’s been imposed. There is a relatively minor legal issue here that means that it all has to be resentenced. I’m not saying that’s necessarily what I’m going to do and clearly enough it is necessary for me to address those sentences where there are no longer matters to be taken into account on a form one or additional sentence or whether there are more than there were before.

BETTS: I do accept that, your Honour, but it needs to be raised because he has had this period of uncertainty and, unfortunately, it wasn’t caused by the offender, it was more to do with the mistakes and probably by the defence and the Crown.

HER HONOUR: No, everybody. And as I understand it to, it was not an issue that exercise the mind to almost anybody until the decision of Illick in the Court of Criminal Appeal and then it became something of a favourite topic for a while and, regrettably, this decision was before Illick. It wasn’t brought to my attention. It went unnoticed by me. It went un-noted by anybody else in the Court. Those who appeared for your client at the time asked that I take the offences into account. The Crown was not heard to gainsay or oppose that and, in fact, signed all the necessary form one and 16BA documents. Everybody got it wrong. (Emphasis added.)

58. This passage reflects no more than the circumstances in which the error occurred on the first sentencing hearing which resulted in the first appeal. The applicant’s counsel then continued to make submissions. It was at the end of that debate between the Bench and bar table that her Honour made the comments referred to in [44] above. She continued shortly after in a passage not referred to by the applicant:

HER HONOUR: …This is a re-sentence, it’s as if it didn’t happen. I am obliged to set out what it’s about, the objective seriousness and all those sorts of things. It seems to me that for those in relation to which there are no changes, it is as simple as simply adopting those portions of the original sentence. That’s what I would be proposing to do. For those where there is a change, it would be a matter of adopting the factual findings, the objective seriousness and where it’s necessary to reassess the extent to which either the addition of further additional offences or the fact that some additional offences are no longer to be taken into account to assess whether or not that, in fact, defects what I perceive to be the appropriate sentence for that group of five where there are changes. But in circumstances where I would otherwise just adopt the factual findings and findings of objective seriousness in relation to those five groups.

And then I am obliged to deal with your submissions, Ms Betts, your submissions about his subjective circumstances and the extent to which, if at all, that should alter the overall sentence because it might affect - I don’t quite understand what it is you’re saying - but I [sic] relation to what the ultimate sentence should be. I certainly understand your submission in relation to special circumstances and your ultimate submission there is that, taking these additional factors into account he needs a longer period on parole than that which I had currently sentenced him to.…

59. This passage is illustrative of the debate that occurred at this hearing as to the issues which had arisen on resentence. Her Honour was very familiar with the case having undertaken the first sentence. The Court of Criminal Appeal in the first appeal had only found error on the limited basis discussed. None of the other grounds of appeal, as I have mentioned, were found to have any merit and were dismissed. Her Honour was expressing the view that the issues were limited to considering the impact of the effect on the overall sentence of the sequences which had erroneously had Commonwealth matters taking into account using the State Form 1 procedure and, on resentence, would be taken into account on Commonwealth counts. This was in the context where there was no relevant challenge to the sentencing judge’s factual findings from the first sentence. It was an appropriate matter to flag with the party’s legal representatives. Neither of them sought to dissuade her Honour from that course or said that this was an inappropriate way to consider the issues that would arise.

60. Additional material had been put before the Court by the applicant and further submissions made by his counsel. Her Honour exposed her reasoning with respect to the additional materials and submissions in the ROS.

61. I do not consider that the applicant has established that a fair-minded person might reasonably apprehend or suspect that the sentencing judge might not bring an open and impartial mind to the resolution of the issues which would arise on resentence. In light of this Court’s reasons in the first appeal, it is unsurprising absent any relevant new or fresh evidence, that there was no challenge to her Honour’s factual findings, including as to the objective seriousness of the offending. The only issues raised by the applicant’s counsel were subjective matters. Her Honour considered those in the ROS and found that there was nothing in the new material which caused her to change her findings from the first sentence.

62. I do not consider her Honour’s remarks concerning whether this Court should have resentenced the applicant rather than remit it back to the District Court are evidence of apprehended bias. It was a long and complex sentence, and her Honour was no doubt managing a busy workload. Having another task added can sometimes lead to expressions of frustration, but that does not mean the task is not completed fairly and with an open mind.

63. In so far as the applicant refers to the ROS and the fact that the same sentence was imposed reflects an apprehension of bias, it must be kept in mind that an assessment of the question of whether there was apprehended bias by reference to the reasons for judgment impermissibly directs attention to whether the judge had in fact prejudged the issue. In Michael Wilson & Partners Ltd v Nicholls (2011) 244 CLR 427; [2011] HCA 48 at [67], Gummow ACJ, Hayne, Crennan and Bell JJ said:

…[A]n allegation of apprehended bias requires an objective assessment of the connection between the facts and circumstances said to give rise to the apprehension and the asserted conclusion that the trial judge might not bring an impartial mind to bear upon the issues that are to be decided. An allegation of apprehended bias does not direct attention to, or permit consideration of, whether the judge had in fact prejudged an issue. To ask whether the reasons for judgment delivered after trial of the action somehow confirm, enhance or diminish the existence of a reasonable apprehension of bias runs at least a serious risk of inverting the proper order of enquiry (by first assuming the existence of a reasonable apprehension). Inquiring whether there has been “the crystallisation of that apprehension in a demonstration of actual pre-judgment” impermissibly confuses the different enquiries that the two different allegations (actual bias and apprehended bias) required to be made. And no less fundamentally, an enquiry of either kind moves perilously close to the fallacious argument that because one side lost litigation the judge was bias, or the equally fallacious argument that making some appealable error, whether by not dealing with all of the losing side’s arguments or otherwise, demonstrates prejudgment.

64. As observed above, the applicant specifically conceded he was not alleging actual bias, but only apprehended bias. His complaint that by adopting the path the sentencing judge did on resentence, in the manner she did and reaching the result that the same sentence was imposed, demonstrates that the sentencing judge prejudged the matter and manifested apprehended bias, impermissibly confuses the relevant inquiry.

65. I would grant leave to argue this ground but dismiss it.

Ground 1 – Procedural Unfairness

66. The essence of the applicant’s complaint in this ground is that the rejection by the sentencing judge of the diagnosis that he had an unspecified paraphilic disorder was procedurally unfair, such as to amount to an error.

67. The applicant referred to the report of Dr Furst of 30 January 2019. That report was tendered in the first sentence and on resentence. On page 9 of that report under the heading “Diagnosis (DSM-5)”, Dr Furst said:

In relation to the offending behaviour before the Court his apparent sexual deviance, [the applicant] meets criteria for the diagnosis of an unspecified paraphilic disorder, which is characterised by recurrent, intense, sexually arousing fantasies, urges or behaviours that are distressing or disabling and that may involve intimate objects, nonconsenting adults, and/or suffering or humiliation of oneself or the partner with the potential to cause harm.

68. He submitted that the sentencing judge should have warned his legal advisors that she was not going to accept this diagnosis, which the Crown had not disputed in its written submissions on the appeal. The applicant says this is reflected in [222] of the first sentence judgment where the sentencing judge said:

…The Crown submissions indicate that sexual desire would appear to have been arising from a paraphilic disorder for which treatment is yet to commence. As will become clear, I am far from convinced that a paraphilic disorder does in fact exist in this offender. I will deal with that in due course.

69. The sentencing judge did return to this issue at [240]-[244] of the first sentence judgment where she said:

He is also diagnosed by Dr Furst as suffering from what is called unspecified paraphilic disorder, but as I understand it, that diagnosis is based on the fact that he in fact committed the offences before me for, and what is said to be the degree of sexual deviance involved. I accept that this so-called disorder is, according to Dr Furst, characterised by recurrent intense, sexually arousing fantasies, urges, or behaviours. This diagnosis as described in that way, does not seem to me to fit the facts surrounding the sentences.

His sexual offending was indeed surrounded by controlling and manipulative behaviour, and there was considerable planning, but it seems to me there is nothing about the sexual activities on the facts that are before me, to indicate that he was playing out any particular fantasy. He was tricking, manipulating and blackmailing women into fellating him, usually in his bedroom, and once or twice in a car or outdoors, but with nothing else. He was doing the same, that is, tricking, manipulating or blackmailing them, in an attempt to get them to give him naked pictures of themselves.

There is no evidence that there were any fantasies surrounding these activities. In fact, it had the hallmarks similar to someone accessing pornography. He also sexually assaulted a number of different women, most of the time in a fairly cold and calculating way, not apparently involving any sexually arousing fantasies, urges or behaviours that are distressing or disabling, but rather involving sexual activity that on the facts, he would seem to have enjoyed. He committed these offences the sexual pleasure, not in my view, as a result of sexual deviance, or at least not on the evidence that is before me.

What he did was illegal. It involved his obtaining of sex illegally because it was without consent, and on the basis of threats. It was not, in my view, the result of any particular form of sexual deviance. I would give little weight to this diagnosis, albeit I accept that Dr Furst is of that opinion, but on the material before me, it seems to me that this diagnosis is not actually available. However, Dr Furst, on the basis of his diagnosis, has suggested that it is something that can be treated. Indeed, there are programs available in the prison, and hopefully he will have access to them.

He is, of course, a sex offender. These are all sexual offences, and there are sex offender programs in the prison. There is a suggestion also by Dr Furst that because these offences were all driven by sexual desires, that when he is due for release he might be treated with anti-libidinal medication. Whether or not that occurs will be a matter for the medical staff and Corrective Services, in due course.

70. It is plain, therefore, from these passages that the sentencing judge did not accept that the diagnosis of unspecified paraphilic disorder was relevant to the facts that she found with respect to the commission of the offences.

71. The applicant notes that on resentence, together with Dr Furst’s report, an additional report of Dr Pusey dated 1 August 2021, a psychologist, was tendered. He says this report also diagnosed him as suffering from unspecified paraphilic disorder. At [56] of that report Dr Pusey said:

Dr Furst additionally diagnosed [the applicant] with a diagnosis of an unspecified paraphilic disorder specifically in relation to his sexual offending. None of the information that I have been provided either through a review of the documents provided for this assessment or through interview with [the applicant] has given me any reason to dispute the validity of this diagnosis.

72. At the resentence hearing on 16 August 2021, there was discussion with counsel for the applicant about [70] of Dr Pusey’s report. Dr Pusey there said:

It is likely to the combined activation of the risk factors identified in paragraph 68-69 which accounts for the behaviour which characterizes [the applicant’s] offending behaviour which although having the appearance of being manipulative or cunning may in fact reflect an incoherence in relation to his view of self which impairs both consequential thinking, as well as his functional capacity within his interpersonal domain of functioning.

73. Having regard to the manner in which that paragraph is expressed, perhaps unsurprisingly, her Honour said that she did not understand that paragraph. She said:

I do need to have this stated quite clearly, Ms Betts, that I don’t understand what that paragraph means and if it’s relied on in that portion of the report that deals with the prospects of recidivism, that section of the report that it’s in, I have no idea what it means. I will leave you to deal with that in due course.

Ms Bett: I will try to contact Dr Pusey to find out what that means.

74. The applicant complained that the sentencing judge did not tell his counsel that she was rejecting the finding of unspecified paraphilic disorder. He submitted that he gave evidence during the resentencing hearing and was not cross-examined by the Crown on that diagnosis. He submitted that her Honour was bound to give warning/notice that she intended to reject the diagnosis (which he said had been accepted by the Crown), and if she had given that warning, then Dr Furst and Dr Pusey could have been called. The applicant submitted that the diagnosis lowers his moral culpability and his suitability as a vehicle for specific deterrence. He submitted that he was denied procedural fairness and is entitled to a re-hearing of the sentence proceedings (citing O’Neal-Show v R [2010] NSWCCA 42 at [27], [50] and [51]; Heath v R [2016] NSWCCA 24 at [40]-[41] and Lehn v The Queen (2016) 93 NSWLR 205).

The Crown’s submissions

75. The Crown referred to [240]-[244] of the first sentence judgment which I have extracted at [69] above. As I have observed, in those paragraphs her Honour did not consider that the diagnosis of unspecified paraphilic disorder fitted the facts as she found them.

76. The Crown referred to the paragraph of Dr Pusey’s report extracted at [71] above. It submitted this was not a diagnosis of unspecified paraphilic disorder, rather an observation that he was not aware of anything which could question the validity of Dr Furst’s diagnosis.

77. The Crown noted that the applicant’s counsel did not make any submissions with respect to the diagnosis of paraphilic disorder, or its impact on sentence, in the resentence hearing. No submissions were made that the diagnosis should be accepted by the sentencing judge notwithstanding her Honour’s earlier conclusions in the first sentencing judgment. The Crown noted that it was expressly recognised by the applicant’s counsel in their written submissions on resentence that the sentencing judge did not accept the offender met the diagnostic criteria of unspecified paraphilic disorder.

78. The Crown noted that the issue of the applicant’s alleged paraphilic disorder was not included in the subjective matters that were raised by the applicant’s counsel during the resentencing proceedings as warranting a differing or additional finding to those made in the first sentence judgment. The Crown submitted that it was open to the applicant’s counsel to re-agitate a submission that the sentencing judge should, contrary to her Honour’s earlier conclusions, accept the diagnosis of unspecified paraphilic disorder and/or that the diagnosis was a material contributing factor to the offending in this case. The Crown submitted that by reason of the first sentencing judgment, the applicant and his counsel were clearly on notice of the sentencing judge’s conclusions with respect to this matter. Further, the sentencing judge had made it plain that absent any other evidence for different findings, it would be unusual in the circumstances for her to make different findings to those contained in the first sentencing judgment.

79. The Crown’s written submissions on resentence were that nothing had changed since the first sentencing judgment with respect to the applicant’s mental health issues.

80. The Crown submitted that in the circumstances, the contention that the sentencing judge was required to give a specific warning or notice in the resentence hearing that she intended to reject the diagnosis of a paraphilic disorder, and that her Honour’s failure to do so resulted in any procedural unfairness, should be rejected.

81. The Crown also submitted that the assertion by the applicant that the Crown ought to have cross-examined him in the resentencing proceedings with respect to Dr Furst’s diagnosis should be rejected. It is unclear what purpose such cross-examination would have had in the circumstances where it was Dr Furst, not the applicant, who had made the diagnosis, and the sentencing judge had already indicated that her conclusion was that the offending was not a manifestation of that diagnosis.

82. The Crown submitted that these were not circumstances where the sentencing judge made findings adverse to the applicant without warning of an intention to do so. The applicant was plainly on notice of the sentencing judge’s rejection of Dr Furst’s diagnosis and the likelihood that, absent additional evidence, she would not change her findings to those made in the first sentence judgment.

Applicant’s Oral Submissions

83. In response to the Crown’s written submissions, the applicant submitted that the Crown had always proceeded accepting that he had been diagnosed with paraphilic deviancy. In those circumstances, he submitted he could not have had warning that the diagnosis was being rejected. He refers to his evidence in chief on the resentence where his counsel led from him Dr Furst’s diagnosis of unspecified paraphilic disorder. He noted that the sentencing judge did not interject that she had rejected the diagnosis.

84. The applicant submitted that it only needed to be established on the balance of probabilities that he suffered from a paraphilic disorder and that if the sentencing judge was going to reject that diagnosis, she should have given prior warning.

Determination

85. A consideration of the application of the principles of procedural fairness in analogous situations can be found in Smith v R [2024] NSWCCA 59 at [6]-[10] per Adamson JA and [34]-[44] per Basten AJA. As a basal proposition, it can be accepted that it would be a denial of procedural fairness if a sentencing judge, without alerting the parties to the possibility that he or she would not accept the joint position of the parties, took a position contrary to that joint position thereby depriving the parties the opportunity to address that possibility.

86. I do not accept the applicant’s submissions that on resentence, the sentencing judge took a position or gave an indication prior to the imposition of the sentence with respect to the diagnosis of unspecified paraphilic disorder and imposed a sentence on him contrary to that position or indication, without giving his counsel an opportunity to address her. Nor do I accept the sentencing judge was required to give any specific indication that she did not accept Dr Furst’s opinion on that matter.

87. The starting point is her Honour’s conclusions in the first sentence judgment with respect to the applicant’s paraphilic deviancy not correlating to the facts of the offending as she found them at [240]-[244]. There was no ground of appeal in the first appeal challenging these findings.

88. It may be accepted that her Honour’s findings were unclear as to whether she rejected Dr Furst’s diagnosis or simply found that on the facts of the offending, it did not apply. I consider the latter is the position on a fair reading of her Honour’s remarks. In the paragraphs identified in [69] above, her Honour compares and contrasts the characteristics of the diagnosis with the facts of the offending. In [243] of the first sentence judgment she says:

What he did was illegal. It involved his obtaining sex illegally because it was without consent and on the basis of threats. It was not, in my view, the result of any particular form of sexual deviance. I would give little weight to this diagnosis, albeit I accept that Dr Furst is of that opinion, but on the material before me, it seems to me that this diagnosis is not actually available. However, Dr Furst, on the basis of his diagnosis, has suggested that it is something that can be treated. Indeed, there are programs available in prison, and hopefully he will have access to them. (Emphasis added.)

89. When read with the balance of the ROS relevant to this point, I consider that where her Honour says that the diagnosis is “not actually available”, she is re-stating her view that the facts of the offending as she found them were inapposite to the characteristics of such a condition as described by Dr Furst.

90. The applicant says that the Crown did not challenge the diagnosis. So much can be accepted for the first sentence proceedings. However, the question of procedural fairness here arises in the context of the resentence proceedings. The sentencing judge had made it plain in the directions hearing on 31 May 2021 that absent further material and submissions, and in light of the Court of Criminal Appeal’s judgment in the first appeal, she was unlikely to make any different findings. It can be readily inferred that this included findings with respect to the applicant’s mental health condition and any impact that may have on the sentence to be imposed. The applicant’s counsel made no submissions in the resentence hearing raising the diagnosis of paraphilic disorder, its asserted material contribution to or connection with the offending conduct and any impact on the applicant’s moral culpability for that conduct.

91. It may have been different if the sentencing judge had accepted the diagnosis in the first sentence judgment but made a finding on resentence rejecting the diagnosis without giving notice to the applicant’s legal representatives so that they had an opportunity to persuade her Honour that the diagnosis should be accepted. That, however, is not what occurred.

92. Even if the diagnosis of the applicant having the unspecified paraphilic disorder was not challenged by the Crown, it was open to her Honour to reject that diagnosis if she identified in the course of the sentence proceedings her reservations about the diagnosis thereby alerting the parties to the possibility that she may reject it.

93. In Goodridge v R [2014] NSWCCA 37, this Court was dealing with an appeal from a judge alone special hearing. The judge had expressed “slight reservations” about the opinions of psychiatrists which were in evidence. Those opinions were relevant to whether the defence had made out the partial defence under s 23A of the Crimes Act 1900 (NSW) as to substantial impairment by abnormality of mind. The judge did not accept those opinions. It was asserted on appeal, relevantly, that there had been a denial of procedural fairness and a miscarriage of justice because her Honour did not advise the parties that she intended to reject the unanimous expert evidence and did not invite the parties to provide further material or call the experts to give further evidence. After considering the exchanges between her Honour and the parties where her Honour had exposed her reservations about the evidence Hoeben CJ at CL (Simpson and Johnson JJ agreeing) said at [136]-[138]:

The remaining exchanges between her Honour and counsel made it clear that her Honour retained the reservations which she had identified. It was open to both counsel to have made an application to her Honour but they declined to do so. That is a very different situation from a case where there has been a denial of procedural fairness. This is not the sort of case where the judge remained silent and failed to reveal opinions thereby depriving the party affected of the opportunity to persuade the judge to change or modify those opinions.

Having clearly expressed her reservations and concerns with respect to the psychiatric material, it was for the parties to decide what course they wished to take. It was not her Honour's role to decide how they should proceed. That was a matter for counsel. Importantly, there was no requirement for her Honour to tell the parties outright that she intended to reject the evidence of the psychiatrists. In fact her Honour may not have reached that conclusion at that point in time given that submissions were continuing. The identification of her concerns was sufficient.

I am satisfied that no procedural unfairness took place and that this ground of appeal has not been made out.

94. In my opinion, the position is analogous here. The applicant’s legal representatives were aware of her Honour’s views on the diagnosis from the first sentence judgment. Her Honour made plain during the directions hearing and in the sentence hearing prior to the imposition of the resentence that, absent further material or submissions, she was likely to make the same findings. This is what she did. There was no denial of procedural fairness.

95. In so far as the applicant seeks to rely on the new reports of Dr Furst, dated 2 May 2025 and Dr Pusey, dated 24 January 2025 with respect to this ground, I would not allow him to do so. Those two reports have been prepared for separate sentencing proceedings shortly coming before the District Court of New South Wales for similar offending. They bear no relevance in my opinion to the question of whether or not the applicant was denied procedural fairness in the resentencing proceedings the subject of this appeal. The fact that Dr Furst’s report confirms the opinions of the authors that the applicant meets the criteria for unspecified paraphilic disorder is beside the point. Dr Pusey’s report is at best ambiguous in this regard (as further described at [117] below) and does not assist the applicant on this ground.

96. In the circumstances, I do not consider the applicant has established this ground. Whilst I would grant leave to argue it, it has not been made out.

Ground 3 – Error of Fact – COVID-19

Applicant’s submissions

97. This ground relates to a statement by the sentencing judge that certain matters, including the impact of COVID-19 related restrictions in the prison system, were taken into account in the first sentence judgment. The applicant contends, correctly, that the impact of any COVID-19 related restrictions was not referenced in the first sentence judgment. Indeed, that could not have been done since the impact of COVID-19 was unknown at that time. The applicant contends, citing Kentwell v R (No. 2) [2015] NSWCCA 96 that once error has been established this court must exercise its sentencing discretion afresh.

98. In oral submissions, the applicant contended that the sentencing judge said she had taken into account COVID-19 restrictions in the first sentencing judgment when that was factually incorrect. At the time of the second sentence, however, it was correct to say that COVID-19 had an impact on the onerous nature of custody and there should accordingly be a reduction in the sentence.

The Crown’s submissions

99. The Crown accepts that the first sentence judgment did not refer to COVID-19 by reason of the fact that, at that time, the pandemic had not been commenced.

100. The Crown submitted that the question to be considered is whether the reference to COVID-19 was a slip or inadvertent misstatement about a matter which did not affect the sentence imposed or whether the sentencing judge mistook the facts and the error was material: House v The King (1936) 55 CLR 499; [1936] HCA 40 at [505]. The Crown submitted the comment made by the sentencing judge with respect to COVID-19 having been taken into account in the first sentence was nothing more than a slip.

101. The Crown submitted that the reference to COVID-19 was made in the context of the sentencing judge explaining the reasons for her finding in the first sentence judgment that the applicant would endure more onerous conditions in custody. The sentencing judge indicated she intended to give the same benefit of that finding to the applicant on resentence.

102. The Crown submitted the slip is explicable as the issue of the impact of COVID-19 on the courses or programmes available to the applicant in custody was raised in submission on resentence. No submissions were made by counsel for the applicant, either orally or in writing, that restrictions in place because of COVID-19 would make the applicant’s time in custody more onerous.

Determination

103. I do not consider that there is any merit in this ground. It was plainly a slip by the sentencing judge in referring in the ROS to COVID-19 in the context of the positive finding she made in the first sentence judgment as to an allowance for the onerous nature of custody on the applicant. The applicant had the benefit of that positive finding which was maintained by the sentencing judge in the resentence. She found there were no additional matters raised in the evidence which would amount to a change in circumstances to make further findings to require an alteration to the non-parole period to be served.

104. As the Crown observed, the issue of the impact of COVID-19 and restrictions that may have been in place because of it making custody more onerous on the applicant was not raised by the applicant’s counsel on resentence. At the resentence hearing, the applicant’s counsel did not ask to be heard on the indicative sentences, the structure of the sentences or the aggregate sentences imposed. She asked for an adjustment to the non-parole period to allow for the better facilitation of treatment as recommended by Dr Pusey to aid his rehabilitation.

105. Matters said to be relevant to the mitigation of sentence are expected to be raised by an offender’s legal representative at the sentencing hearing. This Court is a court of error and is reviewing the exercise of the discretionary judgment of the sentencing judge. It is not rehearing any plea in mitigation of the sentence. Appellants cannot revise and reformulate the case presented. In any event, having had the benefit of a positive finding of the onerous nature of the conditions of custody, I do not consider that the applicant has established that if it had been taken into account, it would have reduced the sentence imposed such as to render a serious injustice to the applicant or cause a miscarriage of justice. In the context of what occurred, the impact of COVID-19 on conditions of custody warranting an additional adjustment to the non-parole period, if thought to be relevant to this case, was obvious. The absence of it being raised by counsel for the applicant allows an inference that it was not thought to have had any merit in terms of reducing the sentence imposed (see Zreika v R [2012] NSWCCA 44; (2012) 223 A Crim R 460 at [79]-[83]).

106. I would grant leave to argue this ground, but reject it.

Ground 4 – New/Fresh Evidence

107. By this ground, the applicant wishes to rely on two new reports, one from Dr Pusey dated 24 January 2025 and the other from Dr Furst dated 2 May 2025. These reports were prepared for use in sentence proceedings pending in the District Court. There the applicant is to be sentenced for one count of sexual intercourse without consent and one count of stalk/intimidate with intent to cause physical or mental harm. The offending occurred in 2008, within the timeframe of some of the offending the subject of this appeal.

108. The applicant’s written submissions state that the applicant seeks to rely on these reports in this appeal to rebut the sentencing judge’s rejection of the diagnosis of unspecified paraphilic disorder. He submits if the sentencing judge’s rejection of that diagnosis is allowed to stand, he will not have access to treatment thus negatively impacting his rehabilitation.

109. Additionally, he submits that if the sentencing judge’s findings as to that diagnosis remains, it will have ramifications on his impending District Court sentence. He submits that the District Court judge “logically has to accept the precident [sic] set by Judge Tupman” (AWS p 4). He contends that by reason of the sentencing judge’s findings rejecting the diagnosis, the District Court sentencing judge would not be able to accept the opinions of Dr Pusey or Dr Furst in the new reports.

The Crown’s Submissions

110. The Crown referred to the principles that an applicant for leave to appeal a sentence is generally bound by the evidence and the case which was advanced at the sentencing hearing and may not seek to enhance the case on appeal: Khoury v R [2011] NSWCCA 118; 209 A Crim R 509 (“Khoury”) at [104] (Simpson J, Davies J and Grove AJ agreeing); Tran v R [2014] NSWCCA 32 at [11]; R v Birks (1990) 19 NSWLR 677 at 683; R v Fordham (1997) 98 A Crim R 359 at [377]; Col v R [2022] NSWCCA 279 at [30]; Barnes v R [2022] NSWCCA 140; 299 A Crim R 483 at [24]; GAR v R [2021] NSWCCA 265 at [45]; Betts v The Queen (2016) 258 CLR 420; [2016] HCA 25 at [2]. Except, however, the rule is not absolute, and an appellate court has the flexibility to receive new evidence where that is necessary to avoid a miscarriage of justice.

111. The Crown submits that the two reports are new (rather than fresh) evidence. That is, that evidence would have been available to the applicant and his legal representatives at the time of the sentence. It notes that the earlier reports of Dr Pusey and Dr Furst (which have been referred to above) were attended in the sentence proceedings. A further opinion from Dr Furst, which was obtained in 2019, could have been obtained with reasonable diligence prior to the resentence hearing in 2021.

112. In any event, the Crown submits that the new reports sought to be relied upon do not establish any miscarriage of justice. The Crown submits that neither report offers any new conclusion on the circumstances advanced in the first sentence proceedings or the resentence. The Crown submits that neither of the reports could have had a bearing on the exercise of the sentencing discretion in any material or significant way. The reports do not change the applicant’s case in respect of the diagnosis of unspecified paraphilic disorder.

113. The Crown submits that the applicant’s contention that the rejection of the diagnosis of an unspecified paraphilic disorder somehow binds the District Court sentencing judge when that judge comes to sentence the applicant for the additional offences, should be rejected. That is because the District Court judge would not be bound to accept a factual finding made by the sentencing judge in these proceedings.

Determination

114. In Lawavou v R [2025] NSWCCA 35, Yehia J (with whom Garling and Cavanagh JJ agreed), from [110]-[116] reviewed the principles dealing with the receipt of new or fresh evidence on an appeal to this Court. Relevantly, those principles include:

(a) “fresh” evidence is more readily admitted than “new” evidence: Barnes v R (2022) 299 A Crim R 483; [2022] NSWCCA 140 (“Barnes”), Hamill J (Gleeson JA and Ierace J agreeing) at [28]. See also Adanguidi v R [2024] NSWCCA 82; R v Abou-Chabake (2004) 149 A Crim R 417; [2004] NSWCCA 356; Khoury; (b) “fresh” evidence has been defined (in the context of trial proceedings) by Mason J in Lawless v The Queen (1979) 142 CLR 659 at 675; [1979] HCA 49 as “... evidence of which the accused was unaware at the time of his trial and... evidence which he could not have discovered with reasonable diligence”; (c) evidence is “new” evidence, if it was available to be adduced at trial, either actually or constructively, but was not adduced: Adanguidi v R at [13] (Garling, Fagan and McNaughton JJ). Evidence is constructively available if it could have been discovered or available at the trial by the exercise of due diligence: R v Abou-Chabake Kirby J (Mason P and Levine J agreeing) at [63].

115. I agree with the Crown submission that, in so far as it is necessary to decide, the evidence now sought to be adduced is the opinions of Dr Furst and Dr Pusey contained in their new reports, as to the offender having an unspecified paraphilic disorder is new evidence in the sense described above. The opinions of those doctors as to that diagnosis, was known at the time of the resentence.

116. The first report of Dr Furst was dated 30 January 2019. It was used in the first sentence hearing. It contained the diagnosis of unspecified paraphilic disorder. It was used again in the resentence proceedings which were almost 2 years after the first sentence judgment. If thought necessary, a further report from Dr Furst could have been sought and tendered in the resentence proceedings. It was not. Nor was a new report commissioned for this appeal. The new report is for different proceedings concerning different offending, albeit of a similar nature committed in the same time period as the offending the subject the resentence. The opinion proffered by Dr Furst in the new report repeats and reinforces his diagnosis of the unspecified paraphilic disorder. It adds nothing new.

117. Dr Pusey’s report dated 1 August 2021 was tendered in the resentence proceedings. The new report was not commissioned for this appeal, but for the District Court proceedings. In any event, in the new report Dr Pusey does not make a diagnosis of unspecified paraphilic disorder. He says, at [74] under the heading “Diagnosis”:

Dr Furst in his report diagnosed Mr Hildebrand with an Unspecified Paraphilic Disorder. Further assessment by appropriately qualified psychiatric and psychological clinicians would be required to clarify the continued validity of this diagnoses [sic], and to provide treatment recommendations appropriate to this.

118. It cannot be said that either of the new reports casts any new light or offers any new conclusions on the circumstances giving rise to the offending to that advanced in the first sentence proceedings or on resentence. It cannot be concluded, therefore, that the absence of this material resulted in a miscarriage of justice because the reports would have had a real bearing on the exercise of the sentencing discretion. Nothing in those reports further advances the applicant’s case with respect to the diagnosis of unspecified paraphilic disorder, its contribution to the offending and impact on the sentencing discretion. Indeed, it could be said that Dr Pusey’s new report does not assist the applicant with respect to the diagnosis.

119. I do not accept the applicant’s submissions that it is necessary to receive the new reports so that the sentencing judge’s rejection of the diagnosis of unspecified paraphilic disorder is overturned. I have dealt with this issue in more detail when dealing with ground one above.

120. Additionally, I do not accept that the District Court sentencing judge will be bound by the findings of the sentencing judge in these proceedings with respect to the reports of Dr Pusey and Dr Furst. Her Honour’s findings with respect to the applicability of the diagnosis to the facts as she found them is a finding of fact that does not bind the District Court judge. Even if it is correct that her Honour rejected the diagnosis rather than held it did not apply to the facts of the offending as she found them, the same result would maintain.

121. I would grant leave to the applicant to argue this ground, but it is not made out.

Conclusion

122. For the above reasons the orders that I would propose are:

123. Extend the time for the filing of a notice of appeal to 27 October 2025;

124. Grant leave to appeal; and

125. Dismiss the appeal.

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Endnotes

Tcpt, 3 November 2025, p 3(6).

Tcpt, 3 November 2025, p 8(32).

After dealing with an application for non-publication orders, the transcript of the sentence hearing proper commences; see Tcpt, 16 August 2021, p 16(45).