R v Simon [2025] NSWSC 309 | Case summary | Zoe

NSWNSWSC

R v Simon

[2025] NSWSC 309

Supreme Court of NSW|2025-04-03|Before: McNaughton J

View on NSW Caselaw

At a glance

Source facts

Court

Supreme Court of NSW

Decision date

2025-04-03

Before

McNaughton J

Catchwords

CRIME – sentence – murder – plea of guilty – where
victim was offender’s daughter’s partner –
where conflict over
property – whether sentence of life imprisonment should be imposed –

Source

Original judgment source is linked above.

Catchwords

CRIME – sentence – murder – plea of guilty – wherevictim was offender’s daughter’s partner –where conflict overproperty – whether sentence of life imprisonment should be imposed –whether full 25% discount forplea of guilty should be imposed – s 25FCrimes (Sentencing Procedure) Act 1999 (NSW) – where specialcircumstances

Judgment

Source: NSW Caselaw (www.caselaw.nsw.gov.au). Converted to plain text by ZoeLaw. Not the official version.

Medium Neutral Citation: R v Simon [2025] NSWSC 309

Hearing dates: 07, 19 November 2024, 24 February 2025

Date of orders: 03 April 2025

Decision date: 03 April 2025

Jurisdiction: Common Law - Criminal

Before: McNaughton J

Decision: Mr Simon is sentenced to imprisonment for 31 years. The Court sets a non-parole period of 22 years commencing on 9 February 2023, and an additional term of 9 years commencing on 9 February 2045 and ending on 8 February 2054.

Catchwords: CRIME – sentence – murder – plea of guilty – where victim was offender’s daughter’s partner – where conflict over property – whether sentence of life imprisonment should be imposed – whether full 25% discount for plea of guilty should be imposed – s 25F Crimes (Sentencing Procedure) Act 1999 (NSW) – where special circumstances

Legislation Cited: Crimes Act 1900 (NSW), s 19A Crimes (High Risk Offenders) Act 2006 (NSW), s 5A Crimes (Sentencing Procedure) Act 1999 (NSW), ss 3A, 21, 25F(2), 30E, 54A, 61 Evidence Act 1995 (NSW), s 4

Where, as here, on a plea of guilty, an agreed statement of facts is relied upon, the sentencing judge is not precluded from seeking further material if the judge comes to the view that the document is inadequate for the sentencing exercise. This is because the judge’s sentencing discretion must be exercised in the public interest: R v Uzabeaga [2000] NSWCCA 381 per Bell J at [34] (Simpson and Dowd JJ agreeing); Nguyen v R [2015] NSWCCA 268 at [45] per Price J (Hoeben CJ at CL and Button J agreeing). In making any findings of fact, those facts must be consistent with the plea of guilty. If I make a finding of fact adverse to the offender, I must be satisfied of that fact beyond reasonable doubt. If I make a finding of fact favourable to the offender, I must be satisfied of that fact on the balance of probabilities: The Queen v Olbrich (1999) 199 CLR 270; [1999] HCA 54 at [27].
In sentencing the offender, I must apply the purposes of sentencing established at common law and as set out in s 3A of the Crimes (Sentencing Procedure) Act 1999 (NSW) (“Sentencing Act”).
The conduct must be denounced, and the offender must be held to account and punished appropriately. The Court must recognise the harm done to the victims and to the community. The sentence must deter the offender, as well as others, from engaging in this type of conduct. The protection of the community is also an important consideration. Further, it is important, both for the offender and the community, that the sentence should promote his rehabilitation to the extent it is appropriate. As for all sentencing exercises, some of the factors pull in different directions.
The offence of murder carries a maximum penalty of life imprisonment (Crimes Act 1900 (NSW), s 19A). A life sentence must be imposed if the level of culpability involved in the commission of the offence was so extreme that the community interest in retribution, punishment, community protection and deterrence can only be met through the imposition of that sentence (Sentencing Act, s 61(1)). In this case, the Crown Prosecutor submitted that a life sentence should be imposed. This was opposed by counsel for the offender. I will consider this important matter in detail later in my remarks.
A standard non-parole period of 20 years for the offence of murder has been specified by the legislature (Sentencing Act, s 54A).
The maximum penalty and the standard non-parole period are both important statutory guideposts which need to be kept in mind when I consider all of the factors relevant to the sentencing task, assess their significance, and then determine the appropriate sentence: Muldrock v The Queen (2011) 244 CLR 120; [2011] HCA 39 at [26]–[27]; Markarian v The Queen (2005) 228 CLR 357; [2005] HCA 25 at [51].
Murder involves the taking of human life. Any sentence must reflect the profound seriousness of this offence in light of the maximum penalty of life imprisonment which has been prescribed by our parliament on behalf of our community. In this case, the life of Damien Conlon was taken. The value the community places upon the preservation of human life is reflected by the need to have the conduct denounced by a sentence appropriate to the circumstances of the case and the particular circumstances of the offender.

| Officer A: | “I understand mate that you’ve rung 000 this morning is that right?” | | Offender: | “I have. Correct.” | | Officer A: | “I understand that someone has been shot on the front lawn.” | | Offender: | “Correct.” | | Officer A: | “Can you tell me who did that?” | | Offender: | “I’m not going to say anything” | | Officer A: | “Ok you’re under arrest for what I suspect to be the murder of a man down here. You’re not obliged to say or do anything. [Anything] you do say or do will be recorded. Do you understand that?” | | Offender: | “I understand.” | | Officer B: | “Obviously there was mention of a firearm?” | | Offender: | “It is inside the house on the kitchen bench. There may be a round in the chamber. You will have to clear it but be very careful.” | | Offender: | “This is what happens when you con people. When you try to take people’s houses off them. So let this be a warning to every con man out there.” | | Offender: | “Listen guys, I am on heaps of medication I have just had heart surgery.” | | Officer A: | “Can you sit your bum down here?” | | Offender: | “Yeah, I can. I have got, I have got miles of medication. I have got miles of medication inside. I have got miles of medication and I’ve got sleep apnoea as well.” | | Officer C: | “OK.” | | Offender: | “And I take a lot of tablets. It’s ok. I’m fine. You don’t need to check me.” | | Offender: | “Oh don’t worry I clipped him behind the ear. This [sic] is no doubt about it. He’s dead. I’m ex-army so I know where to place them.” | | Offender: | “When my father died, he bought me this house. I said to my daughter, to make things easier on you why don’t you build me a granny flat and move into the house? Now they want me to move out and they won’t build me the granny flat. That [sic] wanna take possession. Believe me, as a gold card veteran, homeless. So If you wanna know why, let this be a warning to every con man and scam artist out there […] You don’t fuck around with people like that, you know. This is 60 years of my father’s hard work and I won’t see it pissed up against the fuckin wall.” |

Whether or not the gun was kept out for two days, as opposed to returned to the safe then retrieved on the morning of the murder, was not clear from the Agreed Facts document. At that point in my understanding, that fact potentially could have been relevant to the contested issue as to whether there was an ongoing and settled intention to kill Mr Conlon from the 7 February 2023.
The parties indicated that they wished to engage further with this issue but preferred to have a further oral hearing. A brief hearing occurred on 19 November 2024, at which I was informed that there was additional CCTV footage that was not referred to in the Agreed Facts document. I was further informed that following my email, the Crown served additional CCTV footage (not previously made available) covering the time following the taking out of the firearm on 7 February 2023, and also 8 February 2023. Given the potential relevance of the issue, I gave leave to the Crown, over the objection of the offender’s counsel, to re-open the evidence. The offender’s counsel argued that they had not had sufficient time to look at the additional material, and accordingly I allowed the offender’s counsel as much time as he needed to examine the material. Ultimately, the matter was adjourned to 24 February 2025 for further submissions. In the meantime, further police statements covering the retrieval and copying of the CCTV cameras was served on the offender’s counsel.
When the sentencing hearing continued on the adjourned day of 24 February 2025, I acceded to the offender’s request to make a s 4(2) of the Evidence Act 1995 (NSW) direction to the effect that the law of evidence would apply in relation to the question of whether or not the murder weapon was also taken out of the safe by the offender on the morning of the killing (that is, on 9 February 2023), as the offender said he did, or only on 7 February 2023. Given the potential relevance to the sentencing exercise it was appropriate to make such a direction pursuant to s 4(4) of the Evidence Act (rather than s 4(3) of the Evidence Act as I was not yet of the view whether the question “is or will be significant in determining a sentence to be imposed”).
Three police officers who had made statements in relation to the CCTV retrieval and/or the search of the gun safe were called and cross-examined: Detective Sergeant Adrian Graham (“Detective Graham”), Detective Senior Constable Tammy Smyth (“Detective Smyth”) and Detective Senior Constable Justin Williams (“Detective Williams”).
The evidence on this issue can be summarised as follows:
The CCTV relevantly shows the offender taking out a pistol within a pistol case from the safe once on 7 February 2023.

An empty pistol case (apparently identical to the one seen being put into the safe at 1:35pm on 7 February 2023) was photographed in the living room, but not seized.
Even though police officers took other weapons from the safe, and logged them into the police system, it can be seen from the available pictures, footage and logs that they did not log any empty weapon cases (some of which were clearly visible on the evidence) into the system.
If the firearm remained out of the safe from 7 February 2023, and only the cover was returned later that day, the safe would still contain an empty firearm cover. However, the evidence does not reveal whether or not the total contents of the safe were accounted for in police logs.
The Crown contended I would look at the evidence showing that empty firearms covers were not logged, and would view that evidence along with the other evidence. Mr Nash, counsel for the offender, urged that I should make a “Mahmood type finding” that none of that material would have assisted the Crown particularly in establishing that there was an empty pistol cover in the safe. That was a reference to Mahmood v State of Western Australia (2008) 232 CLR 397; [2008] HCA 1 at [27] in the context of the lack of police evidence in relation to the contents of the safe (given there were police who attended on the day and apparently videoed and photographed certain items from the safe).
In my view, it is not appropriate to approach this portion of the evidence, raised by me in the course of a sentencing proceeding, in a piecemeal fashion. Rather, I will ultimately make any finding as to when the murder weapon was last retrieved from the safe by the offender in the light of all the evidence, keeping in mind that the prosecution has the burden of proof in relation to matters adverse to the offender.
As to the ability to treat the CCTV footage as showing every human interaction with the safe between 7 and 9 February 2023, I cannot make that finding beyond reasonable doubt because it is not clear from the police evidence if all the CCTV files were successfully copied over from the source SD cards. I note the following:

(a) Detective Graham reviewed the CCTV recordings from the laundry covering the gun safe. There were 1,863 activations over a period of 921 days. He confirmed the activations set out at [22(1)] above. He reviewed a second copy of the material which had been copied from a master copy onto a USB (though not copied by him). He reviewed the evidence he had available of the scientific 3D imaging but that was taken when the safe was shut. He did not make further enquiries of other crime scene or ballistics officers in relation to the contents of the gun safe. (b) Detective Smyth stated that Detective Senior Constable Ben O’Connor (“Detective O’Connor”) made copies of the source SD cards onto USBs. She stated that Detective O’Connor and Detective Williams were discussing the SD cards and working out how to have them copied. Detective Smyth later stated it was her understanding that Detective O’Connor or Detective Williams made the copy that she worked from. She believed that it was the 10th, but she could not be certain. As for a further copy that was served on the Director of Public Prosecutions by way of USB that had the 9:37am file missing, she did not know how that occurred. That omission was later rectified. In re-examination, whilst Detective Smyth agreed with the Crown proposition that the missing portion of the CCTV fell outside the 48 hour period before the murder which was served, I note that timing does not account for the missing portion at 9:37am given that fell within the 48 hour period. (c) Detective Williams stated he could not recall if Detective O’Connor was with him on 10 February. He also stated that his attempt to extract the footage with the Cellebrite machine from the SD cards failed, but then on 2 March he successfully made a copy of the information on the SD cards by way of bulk copying and pasting over the thousands of files from the SD cards to a USB. He never crosschecked that every file from the SD cards made it onto a USB. He did not remember speaking to Detective O’Connor about the issues, or any involvement by him.

The offender was 57 years of age at the time of the offence and is now 59 years old.
He has a limited criminal history containing the following:
in 1984, he was convicted for offensive behaviour, possess shortened firearm and cause firearm to be shortened for which he received modest fines;
in 1989, he was convicted for having a mid-range prescribed concentration of alcohol whilst driving a vehicle for which he received a modest fine and was disqualified from driving for 6 months;
in 1991, he was convicted and received a 12 month good behaviour bond for assault; and
in 2007, he was convicted of driving a vehicle with an illicit drug present in the blood for which he received a modest fine and 3 months’ disqualification.
He has never previously been in full-time custody other than one night in 1987 for defaulting on a fine, and he has received no custodial punishments.
The psychological assessment report prepared by Ms Alison Cullen was based on an interview, mental status examination and psychometric assessments conducted with the offender over a period of 3 hours and 45 minutes on 17 September 2024. Ms Cullen also had available to her the offender’s treatment progress notes of psychologist, Mr Dean Oxley (the offender’s former treating psychologist), dated between 26 February 2016 and 25 January 2023; correspondence from Dr Andrew Frukacz, psychiatrist, dated 22 March 2022 and 9 August 2022; the offender’s criminal antecedents, the Agreed Facts on Sentence, and a letter of instruction from the offender’s instructing solicitor. Ms Cullen also had a phone consultation with Mr Oxley on 25 September 2024.
Whilst the Crown did not object to the tender of the report, they required Ms Cullen for cross-examination on the basis that there were significant inconsistencies between the accounts given by the offender to Ms Cullen and those provided to other parties in other documents. The Crown submitted that Ms Cullen’s findings were undermined by those inconsistencies. I also note that the offender did not give evidence before this Court.

Ms Cullen noted that the offender’s twin brother died from a heart attack at 56 years old, three months before their father died in 2021. The offender stated he has still struggled to accept the loss of his father.
As to significant relationships, the offender stated he had been with his first serious partner from around 20 years of age with whom he had three daughters. Linda Simon is the oldest child. The offender’s relationship with this partner dissolved because of his violence towards her after discovering she had withdrawn all the money from their account to cover their mortgage repayments which he stated felt, “like a kick on the head”. He said he sustained regular contact with his daughters every one to two weeks.
One of his daughters had incurred severe disabilities when she was deprived of oxygen at birth and was housed in a group home. When the youngest daughter was in her final years of schooling, the girls’ mother died.
In 1996, the offender reported having a new relationship with a woman who died two years later, suddenly, from diabetes. He stated he struggled with her death and subsequently relapsed on alcohol and drugs to cope with his grief.
His most recent relationship was in 2001 with Helen (a pseudonym). Helen’s former partner apparently committed suicide, and she had two young children. They broke up in around 2005 to 2006 because of incompatibility.
The offender reported that he had had difficulty in all his relationships “mainly due to the sexual abuse” he suffered.
After leaving the Army, he stated he had trouble keeping a job for more than a couple of years at a time. His longest, and most recent, employment was at Sydney Markets, during which time he sustained an injury to his knee, causing complications, including post-surgery infection. He attributed his “major leg injury” coupled with lack of cartilage in his left knee to his subsequent inability to work. He was granted the Disability Support Pension in 2006 and has been unemployed since then. He indicated that his physical immobility hinders his capacity to work while in custody.
The offender claimed his drug and alcohol use commenced after leaving the Army at 16 years old. He used alcohol heavily and also Valium, heroin, cannabis, speed and LSD. He struggled with addiction, with periods of abstention coinciding with starting a new relationship. He had not contemplated the need to attend a rehabilitation facility because he did not realise he had a problem. He reiterated that there were times he felt he was able to abstain.
Following the dissolution of his last relationship, the offender moved to Oberon, and lived with his father. Prior to injuring his spine in 2020, he occasionally used drugs and alcohol, including cannabis, LSD and mushrooms. He was subsequently prescribed multiple medications. His alcohol and drug use was only sporadic, but he had the occasional “bender” between 2020 and 2023.
As a child, he consulted a child psychiatrist when he started experiencing severe migraines. The doctor “molested” him. No action was taken against the doctor although he never returned.
The offender has only had “sporadic” mental health intervention. He was admitted to hospital as an involuntary patient in 1981 following the sexual abuse, stating: “I cut myself apparently. I was out of my skull; that badly intoxicated”. He later suffered from bouts of depression.
He undertook psychotherapy from 2013 to 2015 with the Defence Abuse Response Taskforce (“DART”) psychologists. Once he gained his Department of Veterans’ Affairs (“DVA”) gold card, he accessed his own external psychologist, Mr Oxley. The focus of that intervention was Cognitive Behavioural Therapy and relaxation techniques. Ms Cullen stated that the following strategies were referenced within the progress notes: reframing negative distortions; normalisation of challenges; the practice of gratitude; mindfulness-based techniques to stop rumination; and stress inoculation strategies, such as exercise and talk therapy as well as distraction activities. Ms Cullen reported that the offender’s diagnosed Post-Traumatic Stress Disorder (“PTSD”) symptoms, including flashbacks, panic attacks, nightmares, physiological hyperarousal, increased irritability, suicidality, and need to escape certain locations were well documented, and appeared to have fluctuated throughout treatment. Ms Cullen stated:

The offender also had a therapy dog from November 2016 to September 2019 to manage his PTSD episodes. The dog was responsible for assisting him with his nightmares and pulling him out of crowds or shops when having an episode. The dog apparently failed a particular test (the Public Access Test) and was taken away for rehoming.
Problems with his knee are such that a knee replacement is no longer an option and because he had fallen several times in custody, a decision was made in mid-2023 for him to use a wheelchair for safety. The offender also indicated he had suffered “a spinal cord injury” in 2020 after slipping, resulting in a “paralysis feeling on the right side of [his] body”. He had a catheter inserted and has suffered from kidney infections, one resulting in seven days on a drip in hospital. Hygiene concerns have resulted in him being given a cell by himself.
The offender also reported two heart attacks, one in 2013, and one following the murder, in March 2023. He takes medication for his heart, blood pressure, unstable angina and a sleeping tablet.
His PTSD prognosis has worsened in custody because of the lack of access to regular psychological support. The offender indicated that the personality disorder service checks on him monthly. He reported to have self-harmed in custody.
Ms Cullen reported that the offender confessed he had received several infringements in custody, including for intimidation, although I note no such infringements appear to be reflected in the documents before the court. The offender claims to be triggered in custody for example, getting tense if he is asked to take his clothes off in front of people. He also disclosed that he had been charged with possession of a weapon/implement which related to a homemade knife strictly, he claimed, for his own protection.
The mental state assessment included the Paulhus Deception Scale, which measured two major forms of socially desirable responding, namely self-deception and impression management. He scored high on both sub-scales. Individuals scoring high on both sub-scales tend to be restrained, and generally well-socialised, but when they do have problems, they lack the insight to deal with them and appear rigid.
In relation to the PTSD Checklist for DSM-5, the offender’s score significantly exceeded the cut off, suggesting that he is exhibiting symptoms commensurate with PTSD.
From the phone consultation with Mr Oxley, Ms Cullen reported the following:

Bruce Ross provided an affidavit to the Court. He has been retired since 2015. His career included service as an infantry soldier in the Army, a dog handler in the Army Military Police, and a dog handler with the Air Force Military Police. He also had owned a security business with his wife.
He met the offender at the Oberon pistol club, prior to moving to Oberon in 2016, and they became friends after learning they had both been in the military. By the time of the shooting, Mr Ross had moved to Emu Heights, in Sydney, but he remained in regular contact with the offender, including by phone and text message.
Mr Ross said that by the time of the shooting, he was aware that the offender had both physical and mental health issues. The offender had disclosed to him some of the details of the abuse against him while an Army apprentice and that, by 2021, he was receiving psychological treatment regularly. He described the offender as a bit of a loner, but to him that was not unusual for people with a military background. He remembered the offender speaking affectionately about his grandchildren, Linda’s children to Damien and her previous partner.
During 2022, Mr Ross recalled hearing about the delays with the granny flat. By December 2022, or January 2023, his impression was that the offender’s anxiety about the granny flat had increased significantly. The offender told Mr Ross that he thought Linda Simon was wanting him to be committed to a mental hospital so she could have the house. Mr Ross did not know whether to believe the offender as the offender was “a bit of conspiracy theorist”. For instance, the offender thought COVID-19 was a conspiracy and he was a doomsday prepper, buying food rations to allow him to survive a long time in the event of a catastrophe.
By early February 2023, Mr Ross was so concerned about the offender that he decided to visit him and suggested he come away on a holiday with him and his wife to Western Australia (I infer, at a later time). Mr Ross visited on 8 February 2023 and invited the offender, and the offender agreed to come. Before leaving, the offender asked Mr Ross to take some of his personal property from his home including a metal detector, some tools and some buckets of food rations. Mr Ross stated during the visit the offender made it clear that he was anxious, and that if he left the house he would “lose it” and “lose the property in it”. At that time, Mr Ross says he had no inkling the offender was thinking about shooting Mr Conlon.
Mr Ross received the messages from the offender after the shooting when he was at Emu Heights, and he started driving to Oberon shortly after. He stated that when he spoke to the police, he said he never thought the offender was capable of shooting and killing Mr Conlon or anyone else.

Mr Holles set out various matters in his affidavit he was told by the offender and attached some supporting documents. The information included that at a legal conference with the offender in October 2024, the offender told him of a restorative engagement conference with Lieutenant General David Morrison in Canberra following which he received a handwritten letter of apology. The offender also told him about his ongoing physical health problems, including: a scar on his knee relating to an injury he received whilst working as a security guard in approximately 2001; a scar on his back as a result of an operation in relation to a back injury in 2020; and a series of scars on his left wrist and left forearm, including a scar approximately 5cm by 3cm on his left wrist, which he said were the result of self-harming in custody.
Mr Holles also stated that the offender talked of a recent hospital admission two weeks previously, during which the offender said he was medicated with intravenous antibiotics for three days and had a suprapubic catheter inserted, following nerve injuries to his bladder.
Amongst the documentation annexed to Mr Holles’ affidavit was correspondence relating to the abuse suffered by the offender when he was an apprentice musician in the Army. This abuse was described by the offender in a form for the DLA Piper Review of Allegations of Sexual and Other Abuse (and related matters) in Defence. He stated that he suffered from bastardisation from second year apprentices at the Army apprentices school, and then he went Absent Without Leave (AWOL). As a result, he was picked up by the Military Police and billeted with a Military Police Corporal only known as “Porky”. He stated whilst with him at his unit, he was forced to the ground and sodomised, without consent, and as a minor. He stated that since being discharged from the Army, he had trouble keeping jobs and had bouts of depression. He stated he had trouble with relationships and that he had divorced not long after getting married.
In a document prepared for the Defence Abuse Reparation Scheme, it was reported that the offender was subjected to physical abuse on an almost daily basis, and that he was kicked, punched in the face and burnt with cigarettes by second year apprentices. He also reported being at a different facility where he was physically assaulted and thrown down a flight of stairs. This document also included the abuse involving “Porky”.
The accounts were accepted by the Defence Abuse Reparation Scheme as credible partly because they were made prior to the taskforce and reparations scheme being announced by the Australian Government; other applicants to the taskforce allege abuse at the same location, and of a similar nature, to the abuse alleged by the applicant; and that 25 complaints had been received, including descriptions of physical abuse of the kind described by the offender.
In 2013, Lieutenant General DL Morrison wrote to the offender indicating that his discharge would be based on being medically unfit for service. In 2014, DART wrote to the offender informing him that he qualified for a $50,000 reparation payment, and he received a Certificate of Service and the Australian Defence Medal in 2014 from the Chief of Army.
In 2015, the offender was advised he was eligible for a disability pension from the DVA (after initially being refused) on the basis of an Anxiety Disorder. A letter in 2019 stated that the DVA had accepted the claim for PTSD and erectile dysfunction.
In documentation prepared in 2016 for the DVA, the following answers were provided by the offender to questions included in the form in relation to his disability (which was not defined in this form):

| Which of the following statements apply to you? | The offender ticked: “You are withdrawn and find it difficult to get on with other people” | | How do you believe that your disabilities cause the above problems? | The offender provided the following description: “Mistrust of all people. I am even estranged from my family. After being sexually assaulted in the Army, I lost all trust in people.” | | Do your disabilities affect your life with your family? | The offender ticked “Yes” and provided the following description: “Don’t have any contact with my family in General. They describe me as Abrasive.” | | Do your disabilities affect your social life? | The offender ticked “Yes” and provided the following description: “What social life?” | | Has there been a change in the way you get on with other people since the disabilities occurred (or got worse)? | The offender ticked “Yes” and provided the following description: “2 failed marriages, at least 30-50 jobs (inability to hold down employment due to interpersonal problems/mistrust). Estranged from family due to the change in my character post Army.” | | Does your medication affect your family or social life? | The offender ticked “No” and provided the following description: “Don’t have much of either.” | | Do you have any problems walking? | The offender indicated he suffered from the following: • distance is a problem (most of the time); • I get panic attacks at any time anywhere (most of the time); • Panic attacks can range from fleeing from a person or situation, to full blown breakdowns (some of the time); • This is why I am a loner/shut in. I have completely lost trust in this “World” we live in. Only go out when I have to (most of the time). | | Are there any activities you have given up because of your disabilities? | The offender ticked “Yes” and provided the following activities: “Bushwalking, music, Archery, regular social dinners and outings with family (twice weekly dinners/ Lunches). Was a member of a speiliological [sic] group (caving). All these were replaced with alcoholism, drug addiction and social withdrawal post Army. I hit my wife and was separated soon after.” | | As to how often he undertakes certain activities: | The offender indicated the following: • Rarely or never: visit or have visitors; go out; do a hobby; do voluntary work. • Monthly: play a sport. • 2 or 3 times a week: relax (e.g. reading, watching TV, listening to music). | | List the main ways your disabilities affect the way you live now. | The offender provided the following answer: “I have virtually no social contact. I avoid people and crowded places. Since seeing psychologists and psychiatrists, they have explained this is due to COMPLEX P.T.S.D. My Psychiatrist has told me because the abuse happened during my formative years, behaviours have been ingrained into my personality. My family avoid me because they find me abrasive and controlling. I only have intermittent contact with all my family members. I often feel like the family outcast. I spend a lot of time by myself in contemplation, and self reflection, reflecting on the failures I have endured post Army. In a nut shell, life post army has been one job after another (mostly due to interpersonal difficulties), addictions, self harm and suicide attempts. […] [I] have realised [with the help of a psychiatrist and psychologist], that before I joined the Army, I led a very normal life. A loving family, stable upbringing and solid foundation in Music. […] Fortunately I have overcome the addictions, and with my psychiatrist’s help, am working to try and regain some sense of ‘normality’. It is a very slow and hard road. I am lucky to get 4 hrs uninterrupted sleep a night. I have constant nightmares of all those years ago. I can be in a public place, hear a word, or smell something that triggers a panic attack. To say these are embarrassing and unpleasant is an understatement. This is why I avoid it as much as possible.” |

Ms Cullen opined that the motive to “lure and intimidate” the victim two days before the murder was therefore relevant to his underlying PTSD “as [the offender’s] behaviours were driven to prevent further impending losses from occurring to him. Accordingly, she stated, this assessment revealed a nexus between the offender’s mental health impairments (i.e., cPTSD) and the index offence.
As already noted, the Crown required Ms Cullen for cross-examination. Whilst not taking issue with the diagnosis of PTSD as a result of his Army experiences, the Crown challenged Ms Cullen in relation to her finding a nexus between the PTSD and the index offence. The Crown drew Ms Cullen’s attention to a number of inconsistencies in the material she was more recently provided. That new material had been provided to her on the afternoon before she gave evidence (that is, well after her report was prepared). That new material is summarised above as the material annexed to Mr Holles’ statement relating to his DVA claim. The Crown put to Ms Cullen that the new material, when compared to the offender’s self-reporting, undermined some of her conclusions. Ms Cullen rejected that proposition.
Ms Cullen further responded that one could not separate the diagnosis of PTSD from personality, specifically when the aetiology of that personality stress occurred at such a formative age, or critical development age.
Ms Cullen agreed that if she had the new material prior to interviewing the offender she would have explored the different accounts of the offender’s childhood given to the DVA as opposed to the account given to her. She agreed that there was evidence that the offender had a support network which was at odds with what he had reported to the DVA. Ms Cullen noted that the questionnaire in 2016 was, however, around the time he initiated therapy with Mr Oxley, so it was potentially a situation where his social network could increase across time.
The Crown also pointed to the discrepancy in relation to the account of the sexual acts given to her versus what was said to the DVA. Ms Cullen pointed to the great sensitivity involved in discussing such acts, and there is a lot of shaming around what transpired, so it was one thing to disclose having things done to them, and another where someone is forced to perform sexual acts on the perpetrators. Hence, it was not necessarily a conflict.
Ms Cullen agreed there were various factors which motivated the offender’s conduct, and they were driven by the underlying PTSD.
I accept the evidence of Ms Cullen to the extent that she found the offender suffered from PTSD arising from his abuse in the Army when he was about 15 years old. This is because Ms Cullen’s assessment of PTSD is consistent with the material more recently available from DVA. Further, it was not challenged by the Crown.
It is tolerably clear too that the offender had ongoing personality difficulties, to some extent, throughout the course of his life.
However, the evidence shows that the offender is an unreliable historian not only in relation to his childhood prior to joining the Army, but also more recently in relation to the extent of his social dysfunction. The offender’s account to Ms Cullen of his trauma-filled pre-Army childhood is entirely at odds with what he told the DVA about his loving family and stable upbringing. Further the assessment of Mr Oxley that the offender was “very social” is hard to reconcile with the impression created by the DVA material where he stated in 2016, “what social life”. It could be the case that it was only in more recent years (since 2016) that he developed a social life, but the highly divergent accounts in a reasonably proximate period mean I am of the view that I cannot rely upon the offender’s account without objective support.
I note the offender’s counsel, Mr Nash, conceded that the offender did not rely upon his account to submit that the offender had an extremely deprived childhood. I note too, that it was accepted the offender’s parents had separated and it was not controversial that he had had a step-mother. I accept these facts. Mr Nash reiterated, and, as noted I have accepted, that the most important evidence is the abuse he suffered when in the Army at age 15, and the consequential PTSD diagnosis.
However, I am unable to accept that the offender’s PTSD was directly causally related to the murder. I do not accept the account from the offender that he had not planned to kill Mr Conlon until Mr Conlon smirked at him and he lost control (or, as he put it “lost his shit”). Not only is the offender an unreliable historian, this self-serving statement is, in my view, entirely inconsistent with the cold and calculated demeanour of the offender when he took out the murder weapon two days before the murder and stated, “that’s the one that is going to put him to sleep”, and “fucking Damien, you’re fucking gone”. Further, it is at odds with the discharge of multiple shots at Mr Conlon. It is also inconsistent when viewed in the context of the pause between the shots taken inside the house and the final fatal shot on 9 February 2023 when the offender followed Mr Conlon out of the house to the location where Mr Conlon had collapsed in clear and alarming physical distress as a result of being shot inside the house. As noted, at this point, the offender calmly and carefully aimed at the head of Mr Conlon, when the offender stated, “bye bye Damien” and calmly walked away.
Whilst I do not find that the offender’s PTSD triggered an immediate emotional response on the day of the killing which he found difficult to control in the moment, I find the offender’s PTSD provides some underlying explanation for the personality problems which ultimately led to the offender’s disproportionate response to the housing dispute with his daughter and her partner. In all of the circumstances I find that the offender’s underlying mental disorder diminishes, but only to a limited extent, the offender’s moral culpability.
I now turn to whether a life sentence should be imposed upon the offender.

The maximum penalty for murder is life imprisonment*,* but there remains a discretion for a court to pass a lesser sentence: Crimes Act, s 19A*;* Sentencing Act, s 21(1). As noted above, the Crown submitted that a life sentence should be imposed.
As noted above, s 61(1) of the Sentencing Act provides that a court is to impose a sentence of imprisonment for life on a person who is convicted of murder if the court is satisfied that the level of culpability in the commission of the offence is so extreme that the community interest in retribution, punishment, community protection and deterrence can only be met through the imposition of that sentence. The burden falls on the Crown to establish, beyond reasonable doubt, that a case falls within s 61(1): R v Merritt (2004) 59 NSWLR 557; [2004] NSWCCA 19 at [35].
The case law makes clear that in assessing the level of culpability of the offender in the commission of the offence for the purposes of s 61(1), the Court should take into account the circumstances surrounding or causally connected to the offence. This exercise not only includes consideration of the objective seriousness of the offence, but also subjective matters, such as the offender's background, criminal history and any mental disease, disorder or incapacity. Even if these matters tend towards the imposition of a life sentence, there remains a discretion for the Court to impose a fixed term. In the exercise of instinctive synthesis, consideration of subjective matters such as remorse, confessions, pleas of guilty and their timing, and the offender’s prospects of rehabilitation are germane. Some matters may be relevant to both stages of the assessment: Sentencing Act, ss 61(3) and 21(1); R v Harris (2000) 50 NSWLR 409; [2000] NSWCCA 469 at [93]; Rogerson v R; McNamara v R [2021] NSWCCA 160 at [634]–[635].
As noted above, the Crown submitted that the Court would find the offender formed the intention to kill Mr Conlon at least two days before the murder, and that he lured him to the Oberon property under false pretences with the settled intention of killing him. The Crown contended that the offender’s actions amounted to a pre-planned execution style killing, and that the offender’s level of culpability is so extreme that the community interest in retribution, punishment, community protection and deterrence mandate the imposition of a life sentence.
Mr Nash submitted that a life sentence should not be imposed. Whilst he accepted that the offending here is “above mid-range”, Mr Nash submitted that there are a number of factors tending against the imposition of a life sentence. In contending that the Court would not find beyond reasonable doubt that the offender had a settled intention to kill for at least two days, he highlighted a number of matters. He pointed to the phone call on the morning of the murder which was made to the daughter and not to Mr Conlon and there was no direction to the daughter to send Mr Conlon. He did not tell his daughter not to come, rather he asked if she was coming. This created tension between the possibility of them both coming and the asserted settled intention to kill Mr Conlon. Mr Nash also pointed to the ambiguity of the use of the plural when talking to the IGA worker the previous day. In addition, Mr Nash pointed to the delay of several minutes between Mr Conlon arriving at the Oberon property and the likely beginning of the shooting of Mr Conlon, culminating in the devastating final lethal shot to his head. Mr Nash also submitted that the offender’s agreement to go on holiday with Mr Ross, and to give him some of his possessions are not consistent with the offender’s settled intention to kill Mr Conlon.
Mr Nash contended that the court should not infer, beyond reasonable doubt, that the offender had an enduring intention to kill between 7 and 9 February, but should infer that the intention only crystallized once Mr Conlon “smirked” at the offender.
In my view, the combined effect of the undisputed evidence is such that I am satisfied beyond reasonable doubt that the offender had a settled plan to execute Mr Conlon. I find that the intention to kill Mr Conlon was formed by Tuesday 7 February 2023.
Even though the phone call falsely reporting that Mr Conlon’s belongings had been stolen was made to his daughter, the call was made at a time early in the morning and was clearly designed to lure Mr Conlon to the Oberon property. The offender clearly admitted that. I also take into account that Linda Simon had caring responsibilities involving young children, known to the offender, and at that time in the morning would be highly unlikely to be able to quickly attend.
I also take into account the words uttered by the offender when he took the murder weapon out of the safe on 7 February 2023 and the tone in which he said those words. In addition, I note the words said to the IGA worker, which in the context of the other evidence, support a continued intention to kill. I take into account that the offender must have gone to his safe to get out the murder weapon prior to Mr Conlon arriving at the front door, and that the weapon was either pre-loaded, or loaded by the offender that morning.
I have also viewed the disturbing and chilling video of the final shooting of the already wounded Mr Conlon. I note the calm and calculated manner in which the offender shot Mr Conlon, the words “bye bye Damien”, the tone of his voice, as well as the offender’s multiple admissions to the shooting. Whilst it is unclear (because there was no autopsy) how many times the offender shot Mr Conlon, it was clearly more than once. It can also be noted that the offender boasted about his prowess in shooting Mr Conlon to the police, as set out at [16] above. Further, the use of the firearm not only demonstrates premeditation and planning, it also meant that there was no realistic opportunity for Mr Conlon to defend himself.
I also agree with the Crown submission that in the moments between being shot inside the house and the point at which he was finally killed, Mr Conlon must have been in a state of abject terror, contemplating what would inevitably happen to him. I further agree with the Crown contention that the offender knew that the deceased was the father of two children, the stepfather of two others and the loved partner of his daughter. He would have known and considered for at least two days the catastrophic effect Mr Conlon’s murder would have had on his daughter and her four children. Such awareness is relevant to the offender’s culpability: R v Mark Lewis [2001] NSWCCA 448 at [67]. I note, too, though it bears little weight on sentence, that this is a particularly tragic aspect, given the children were also the offender’s own grandchildren and his own daughter was the mother of those children.
Further, I note that Linda Simon and Mr Conlon had been intending to live in the house where Mr Conlon was killed, once renovations were complete. That the murder occurred in their intended future home also impacts upon Mr Conlon’s family.
All these factors together significantly elevate the seriousness of the offending.
However, given the offender’s mental disorder provides some underlying explanation for his entirely disproportionate response to his short-term housing problem, and, as I have found, reduces the offender’s moral culpability to an extent, I am unable to determine beyond reasonable doubt that a sentence of life imprisonment is the only way of meeting the community interest in retribution, punishment, community protection and deterrence. Accordingly, I will impose a determinate sentence upon the offender. I am of the view, though, that the objective seriousness of the offending is very high, and well above mid-range.

Linda Simon read to the Court a victim impact statement.
Pursuant to s 30E(3) of the Sentencing Act, I consider that it is appropriate to take this statement into account. I do so on the basis that the harmful impact on Mr Conlon’s family is an aspect of the harm done to the community as a whole by the actions of the offender. It is also an important way for the Court and the community to find out more about Mr Conlon.
Linda Simon stated how difficult it was to put into words how the actions of the offender had taken away her fiancé and father to her two youngest boys; a man who was also a brother, a son, and a good friend to many. She said how she was a shell of her former self because she was unable to put into the right words the suffering through the pain, sorrow, fear, anger and emptiness she feels since Damien’s life was taken. She spoke of how the offender had held her sons within hours of them being born, and told them he loved them, and would not let any harm come to them, yet he killed their father and stepfather, harming them in a way that can never be repaired. His actions have resulted in loss, grief and a strong sense of betrayal.
Linda Simon recounted how Damien had moved to Australia from the County Sligo in Ireland to pursue a better life. He lived fully, loved fully and laughed fully.
Almost daily her sons have questions she cannot answer concerning why their grandfather wanted to hurt them so badly. Each of the children are, and will be, deeply affected by Damien’s death, and even their second-youngest son who was only 2 years old at the time of the crime and is now 3 years old asks “why is daddy dead?” and other heartbreaking questions.
When her fiancé left that morning, he was just going to work and would be home in a few hours. Linda Simon set out how she did not take stock of his attire, or the blue of his eyes and the smell of his beard as he kissed her goodbye for what she did not know was the final time.
She now struggles to enjoy the company of friends and family and struggles to know how to enjoy herself. She and Damien shared everything about themselves with each other and despite difficulties in the relationship with her father, Damien encouraged her to be forgiving and supportive.
Linda Simon has had to force herself to grieve sporadically because she must nurture the boys through their grief. Damien will miss all the small and large events of the boys’ lives and it breaks her heart that her boys will struggle with the emptiness of the absence of a father because of the actions of the man that should have been their grandfather.
Linda Simon also set out how Damien’s birth family in Ireland struggle daily. Leanna, his baby sister, still goes to call him to check in, get advice and have a laugh, but cannot. His goddaughter, Leanna’s eldest child, still cries for her godfather and aches to hear from him again. His little brother Philip struggles to cope with the way Damien died. Damien’s parents, Dermot and Ethel, suffer from indescribable pain from losing their son. Damien’s big brother, John (known as Moss) finds it hard to believe his brother has gone.
Damien’s death has meant that Linda Simon now finds it difficult to focus on her career, something she was previously passionate about. It has taken her 18 months to want to return to work which has caused financial hardship as well.
Linda Simon’s victim impact statement was powerful and provided the Court with insight into who Damien was and the impact of his death on her, their children, his family in Ireland and others. I am acutely conscious of the fact that neither words nor the imposition of a sentence can restore the loss of a loved one or assuage the grief caused to Damien’s family and friends. But it is important that the impact of the offender’s actions upon the victim’s loved ones be recognised and never forgotten. On behalf of this Court, I extend my sympathies and sincere condolences to Damien’s loved ones.

R v Simon

At a glance

Court

Decision date

Before

Catchwords

Source

Catchwords

Judgment

JUDGMENT

General sentencing principles

Factual findings

Material tendered on sentence

Factual findings for the purposes of sentence

Background

The offender

The deceased

The agreement

The eviction notice

7 February 2023

8 February 2023

The murder

9 February 2023

Post-offending

Arrest

Judicial query about whether the murder weapon remained out of the safe between 7 and 9 February 2023

Subjective circumstances of the offender and other considerations

Subjective material as reported by Ms Cullen in her report

Account of the offending to Ms Cullen

Other evidence relied upon by the defendant

Bruce Ross

Dominic Holles, Solicitor

Consideration of nexus between the offender’s mental health impairments and the offending

Consideration of imposition of life sentence and objective gravity of the offending

Consideration of whether the offender should receive the full 25% deduction for his plea of guilty.

Hardship in custody

Rehabilitation

Victim impact statement

Comparative cases

Special circumstances

Other sentencing considerations

Sentence

Endnote

Parties

Legislation Cited (6)

Cases Cited (7)

Cited By (1)