R v Monteiro

The supervision orders

1. On 3 April 2020, that is, four days before the offender's sentence was due to expire, the Supreme Court made an interim supervision order for an initial period of 28 days. Further applications were made to the Supreme Court to renew the interim supervision order which were granted (see State of New South Wales v Monteiro (aka Lowe) (No 3) (Preliminary) [2020] NSWSC 350).
2. On 6 July 2020, the Supreme Court made an extended supervision order for a period of 5 years to date from 6 July 2020 and expire on 5 July 2025 (see State of New South Wales v Monteiro (Final) [2020] NSWSC 881).
3. At this stage I note that the objects of the Crimes (High Risk Offenders) Act as set out in s 3 of the Act as follows: "(1) The primary object of this Act is to provide for the extended supervision and continuing detention of high risk sex offenders and high risk violent offenders so as to ensure the safety and protection of the community. (2) Another object of this Act is to encourage high risk sex offenders and high risk violent offenders to undertake rehabilitation."
4. Section 5B of the Act provides as follows: "The Supreme Court may make an order for the supervision in the community of a person (an "extended supervision order") if: (a) the person is an offender who is serving (or who has served) a sentence of imprisonment for a serious offence either in custody or under supervision in the community, and (b) the person is a supervised offender (within the meaning of section 5I), and (c) an application for the order is made in accordance with section 5I, and (d) the Supreme Court is satisfied to a high degree of probability that the offender poses an unacceptable risk of committing another serious offence if not kept under supervision under the order."
5. In the extended supervision order proceedings, evidence was heard from two forensic psychiatrists. Each psychiatrist, that is, Dr Eagle and Dr Furst had assessed the offender as being well above the average risk of reoffending (see State of New South Wales v Monteiro (Final) at [28] and [38]). Each psychiatrist was also of the opinion that the offender's risk level was unlikely to change in the short to medium term (see State of New South Wales v Monteiro (Final) at [35] and [42]).
6. Dr Eagle noted the following conclusions: "[The defendant] did not display or describe signs or symptoms of a major mental illness such as a psychotic disorder or major mood disturbance on assessment. He has been described in various clinical and case notes as grandiose, entitled, agitated, hyperactive, pressured and erratic. … [The defendant] has been diagnosed on various occasions with a mood disorder. It is apparent that he has a history of severe emotional dysregulation from early childhood that is manifested in highly problematic behaviours including repeated and severe aggression. He has also been described as pervasively depressed at times and hypomanic at others. [The defendant] has been diagnosed with post-traumatic stress disorder (PTSD), arising both from earlier experiences in the correctional environment and childhood sexual abuse. … [The defendant] likely has a substance use disorder in remission, in a controlled environment…[The] use of substances has been implicated as a contributing factor in some of his alleged offended behaviours. He has criminal charges arising from the use of substances. Emotional dysregulation and mood disturbance are exacerbated by the use of substances. [The defendant] has a severe personality disorder. He has been diagnosed with narcissistic personality disorder and anti-social personality disorder. I am of the view that he would satisfy the criteria for those personality disorders on the information available and based on a psychiatric assessment. He has displayed a pervasive pattern of behaviour since childhood including failure to conform to social norms regarding lawful behaviours; deceitfulness (for instance the use of aliases); impulsivity; aggression; reckless disregard for the safety of self and others; and lack of remorse with evidence of conduct disorder before the age of 15 years old. He has been repeatedly described and continues to display a grandiose sense of self-importance; belief he is special and/or unique; has a sense of entitlement; behaviours that are interpersonally exploitative; a lack of empathy and shows arrogant haughty behaviours or attitudes. I am of the view that [the defendant] has a high loading of psychopathic traits based on assessment using the PCLR (Psychopathy Checklist Revised). The PCLR is a structured professional judgment tool designed to identify those with a psychopathic personality style or traits. A high score on the PCLR has been associated with a high risk of violence and sexual offending in research literature".
7. Dr Eagle also noted at [32]: "Most significant of these risk factors would appear to be [the defendant's] lack of insight or acceptance of responsibility for his previous offending which appears to be an ongoing barrier to his ability to address the factors associated with his risk of future offending. [The defendant's] risk of committing a further serious offence would appear to be highest in the context of intimate relationships, and involve a sexual offence against an intimate partner. His lack of insight into previous problematic relationships…or willingness to engage in meaningful strategies to acknowledge and address the problems associated with those relationships (involving his own conduct and vulnerabilities, rather than merely attributed to the intimate partner) would be that most significant barrier to his rehabilitation".
8. Dr Furst noted as follows at [38]: "A review of [the defendant's] criminal/relationship history is indicative of a pattern of both violent and sexual offending perpetrated against intimate partners, episodes of property damage and threats during periods of rejection and/or emotional conflict and potentially even in the absence of conflict or heightened emotions. His past offending appears to have been largely driven by a combination of emotional deficits, anger issues, negative attitudes towards women, a need for power, control and possessiveness in his intimate relationships and revenge themes. Those tendencies, traits and manifestations, which largely stem from his personality disorder are likely to resurface in future relationship with women. [Another factor] of significant concern in relation to his past offending and risk of future offending is his pathological level of denial in relation to virtually all previous offences, including a pattern of taking matters to trial, appealinh against convictions and severity of sentence, and ongoing denial of offending such as the denial that has persisted over the last 12 years in relation to [the index offence of January 2008]. In my opinion, his pathological level of denial, coupled with a pattern of continual rejection of authority figures and his personality disorder, is a far more ominous scenario than a sex offender who lacks insight into offending and/or has cognitive distortions facilitating future offending, the latter being much more amenable to therapy/interventions. Furthermore, the manipulative and threatening tendencies of [the defendant] towards his victims and his contempt for the criminal justice system, the courts, Corrective Services, psychiatrists and psychologists indicates he is completely lacking in any motivation to address his offending behaviour or underlying emotional deficits."
9. Dr Furst was of the opinion that without formal supervision in the community the offender would: "Likely pose an unacceptable risk of sexual or physical violence of a serious nature to his current and/or future female partners, especially in the form of control of his partners, threats, intimidation and increasing risk when [he] is rejected and/or perceives rejection".
10. Fagan, J observed as follows at [68]: "It appears to me that the most important aspect of supervision is for the DSO(Department Supervision Officer) to obtain particulars of any female partner of the defendant when and if he commences an intimate relationship, so that a judgment can be made as to whether the partner should be informed of the defendant's background. To this end, I have included condition No 4 in the schedule to the ESO. This requires the defendant to answer truthfully questions from his DSO about his location, his activities and his associations. Condition No 15 requires him to inform the DSO if he commences an intimate relationship. Past experience of Corrective Services' attempts to supervise the defendant in the community have shown that he cannot be relied upon to provide accurate information. If he fails to do so under conditions 4 and 15 he will be liable to prosecution for breach of the ESO under s 12."
11. Included in the interim supervision orders made on 3 April 2020 were the following conditions:

• Condition 3 - The defendant must comply with any reasonable direction given by his DSO or their delegate from CS New South Wales (Corrective Services New South Wales) for the enforcement and implementation of the ISO/ESO or any condition of the order. Where a direction may conveniently be given in writing (or is required to be given in writing), it may be given electronically including by SMS or other messaging service.
• Condition 23 - The defendant must give his DSO a list of all devices he uses to communicate with or to access the internet as soon as practicable and, in any event, no later than within 24 hours of obtaining the device or joining the service or application. This includes phones, tablet devices, data storage devices or computers ('the Devices'). This also includes the details of telephone numbers, service provider account numbers, email addresses, login names or other usernames and relevant passwords and codes, used by the defendant and the nature and details of the internet connection as directed.
• Condition 27 - The defendant must advise the DSO of any change of the inventory of the devices listed in condition 23.
• Condition 33 - The defendant must not change his name from Simon Monteiro or use any other name without the approval of his DSO.
• Condition 34 - The defendant must notify the DSO of all login names, passwords and email addresses that he uses other than those provided to the DSO under condition 23, on any internet site (including social networking sites), any online communication applications or any third party sites or applications that require the user to have a user identification name or login email.

1. Included in the extended supervision order made on 6 July 2020 were the following conditions:

• Condition 3 - The defendant must comply with any reasonable direction given by his DSO or the DSO's delegate from Corrective Services New South Wales for the enforcement and implementation of the ESO or any of these conditions. Where a direction may conveniently be given in writing (or is required to be given in writing) it may be given electronically including by SMS or other messaging service.
• Condition 13 - Before commencing any form of employment, volunteer work or educational course the defendant must advise the DSO of the nature and place of the relevant activity and the contact details of the person in charge and/or responsible for the defendant's involvement and participation.
• Condition 16 - The defendant is to notify his DSO of: 1. Any user name and password for any social media networking app that he may utilise and for any dating app or website that he joins or with which he affiliates, and 2. Any social club or similar organisation that he may join.
• Condition 17 - The defendant must give his DSO a list of all devices he uses to communicate with or to access the internet as soon as practicable and, in any event, no later than within 24 hours of obtaining the device or joining the service or application. This includes phones, tablet devices, data storage devices or computers ('the Devices'). The details to be provided shall include, as directed, telephone numbers, service provider account numbers, own email addresses, login names or other usernames, relevant passwords and codes used by the defendant and the nature and details of the internet connection.
• Condition 23 - The defendant must notify the DSO of all login names, passwords and email addresses that he uses, other than those provided to the DSO under condition 16, on any internet site (including social networking sites), any online communication applications or any third party sites or applications that require to have a user identification name or login email.
• Condition 24 - The defendant must not change his name from "Simon Monteiro" or use any other name without the approval of his DSO.

Communication with Community Corrections during the Interim Supervision Order between 3 April 2020 and 5 July 2020

1. On 6 April 2020, the offender provided a phone number to a Community Corrections Officer via an email address. The offender indicated that the number provided was "new and only contact number" and that he had given away his iPhone, iPad and MacBook that day. The number provided was also the contact number for his partner Carol Langley.
2. On 7 April 2020, a Community Corrections Officer met with the offender and explained his interim supervision order to him. The offender signed the acknowledgment in relation to the interim supervision order and its conditions.
3. Pursuant to condition 3 of the interim supervision order, the Community Corrections officer issued the offender with several written directions, including the following: 1. You are hereby directed not to access social media accounts which include but are not limited to Facebook, Instagram, Snapchat, Hangouts, WhatsApp, Pinterest, Plenty of Fish, Oasis, LinkedIn, Twitter or any dating websites/applications unless approved so in writing by your DSO. 2. You are hereby directed to provide a detailed inventory (including passcodes, login and usernames, serial numbers, IME numbers and phone numbers) of all devices that you currently have in your possession including but not limited to mobile phones, tablet devices, computers and external storage devices. Furthermore, you are directed to provide details of all email addresses that you use including the usernames and passwords. You must provide this inventory within 48 hours of the date of this direction. Furthermore, you are directed to advise your DSO of any change of the inventory that you supply to your DSO. 3. You are hereby directed not to destroy, tamper with, or interfere with your mobile devices, and computers (including SIM cards and storage devices). Furthermore, you are hereby directed that you must not delete any content from your mobile phone or any other electronic device. 4. You are hereby directed not to have on any phones, tablet devices, data storage devices, computer or other devices, software or applications that are designed to erase the history or hide the contents of the device. 5. You are directed that you are only to possess and use one mobile phone device and one SIM card at any given time. 6. You are directed not to access any other person's mobile device for any reason and you are not to permit any other person to access yours for any other reason.
4. The offender acknowledged those directions and signed an acknowledgment of them. After signing the acknowledgment, the offender indicated that he would dispose of all his devices and use his partner's phone. It was explained to the offender that in doing that it would be in a breach of the direction.
5. On 8 April 2020, the offender phoned his supervising Community Corrections officer and indicated he would purchase a "cheap phone and SIM card".
6. On 23 April 2020, a Community Corrections Officer sent an email to the offender requesting that he provide an inventory of all his devices and if he no longer had any he would still need to complete one stating such.
7. On 27 April 2020, a Community Corrections officer received an email from the offender's partner, Langley, indicating that the offender no longer had any electronic devices. She also indicated that the offender would purchase a new phone in the near future.
8. On 28 April 2020, the Community Corrections Officer reminded who he thought was Langley via email that the offender is to provide a signed inventory in relation to any electronic devices and a mobile phone for himself as a matter of urgency. The Community Corrections Officer received a response from the email address indicating that the offender would complete the inventory that night and purchase a phone the following day.
9. On 29 April 2020, there was an email exchange between the Community Corrections officer and Langley. During that exchange the Community Corrections officer was advised that the offender had purchased a phone and was provided with a phone number.
10. On 30 April 2020, the Community Corrections officer received an email under the assumption that it was Langley who had sent the email attaching an inventory that the offender had signed claiming that he had no electronic devices, apart from his recently purchased mobile phone, being an Optus X mobile handset (IMEI number provided).
11. On 6 May 2020, the Community Corrections Officer met with the offender and issued a formal written direction in relation to condition 23 and 25. In particular the following directions were issued: 1. You are not to have a third party contact Corrective Services New South Wales on your behalf except in an emergency. 2. You are not to use devices belonging to another person except in an emergency. 3. If any of the devices are destroyed, damaged or lost you must notify the DSO within 24 hours. 4. You must not dispose of or sell any of the devices without prior approval of the DSO.
12. The directions were again issued to the offender with regard to condition 23 and 25 of the interim supervision order. The offender signed these directions acknowledging them.

Communication with Community Corrections during the Extended Supervision Order from 6 July 2020

1. On 6 July 2020, the offender met with a Community Corrections officer who completed the acknowledgment form with the offender. The offender signed the acknowledgment as Simon Lowe, in breach of condition 24, and was later given an official warning with regards to using another name.
2. On 15 July 2020, the Community Corrections officer met with the offender at the office of Gosford Community Corrections. During the conversation, the offender indicated that he did not use any form of social media or dating applications, nor does he communicate via any form or device other than his email address and his mobile phone, which he had previously provided the details for to Community Corrections.
3. In the same conversation, the Community Corrections officer noted that the offender had previously discussed his need to study and asked how he does this on his phone. The offender claimed that he occasionally uses the library computers and reads on his mobile phone. The offender was informed that he would need to provide details of any computers used, and community-based computers would fall into that category. The offender later noted that the only email address he used was 2020ourhome@gmail.com.
4. On 22 July 2020, a Community Corrections officer met with the offender at his home address. The offender was told that the Community Corrections officer wanted to complete a telecommunications devices and internet access form with him. The offender provided the address 2020ourhome@gmail.com as being the only email address he uses. During the conversation, the offender again asked the Community Corrections officer about using public computers and was informed that he would need to provide the IP addresses and any other relevant details, such as the details of the internet connections. The offender was advised not to use any public computers unless he was able to provide these details.

Sequence 1: Fail to comply with extended supervision order (condition 24 - use of other name - Simon White)

1. At approximately 12.40 pm on 21 July 2020, the offender attended Legends Gym in Kensington. The offender, when signing into the gym for a casual one day trial, used the name "Simon White". When completing the waiver form for the gym the offender again used the name "Simon White".

Sequence 2: Fail to comply with extended supervision order (condition 24 - use of other name - Adam Lowe)

1. At approximately 5.45 pm on 21 July 2020, the offender attended The Oakes Hotel in Neutral Bay with his partner and another associate. The offender used his brother's name, "Adam Lowe", when signing into the venue due to the pandemic.

Sequence 3: Fail to comply with extended supervision order (condition 17 - use of other device - iPhone X and Huawei Nova 3E)

1. Between 10 July 2020 and 24 July 2020, the offender was in possession of and using an Apple iPhone X. Call charge records show that the offender used the Apple iPhone and that in excess of 200 calls were made and/or received as well as 130 messages being sent and/or received. The call charge records for the iPhone show that the offender was in contact with several of his associates, legal representatives and family members. The offender was also in possession of a used Huawei Nova 3E mobile phone (IMEI number provided). The offender had been in possession of this phone and using it since 6 April 2020 despite claiming that he had disposed of it on several occasions.

Arrest and seizure of electronic devices

1. On 18 August 2020, the offender was arrested and charged for failing to comply with his extended supervision order, the conduct being the offending outlined for sequences 1 and 3 above. When New South Wales Police arrested the offender they seized the following devices: 1. Apple iPhone X (the subject of sequence 3); 2. Huawei Nova 3E phone (the subject of sequence 3); 3. Optus X Start handset (IMEI number provided); 4. HP laptop computer (serial number provided); 5. Apple MacBook laptop computer (serial number provided); and 6. Several external hard drives.
2. New South Wales Police electronically examined the devices that were seized. As a result of this analysis, the offender was charged with the following further offences of failure to comply with his interim supervision order and extended supervision order.

Count 1 - Fail to comply with interim supervision order (condition 23 - use of other devices, being the iPhone x, Huawei Nova 3E and MacBook computer

1. As a result of the devices that were seized by police being examined, the report showed that the offender was using the iPhone X, Huawei Nova 3E phone and MacBook Pro during the time that he was subject to the conditions of his interim supervision order, and after he had declared that they had been given away, that being between 30 April 2020 and 6 July 2020.
2. The reports show emails and text messages being sent and/or received by the offender and access to certain websites including his online TAFE course, were used on the devices.

Count 2 - Fail to comply with extended supervision order (condition 17 - use of other device - Mac computer)

1. As a result of the MacBook computer being examined, the report showed that the offender was using the device during the time that he was subject to the conditions of his extended supervision order. The report shows emails and text messages being sent from and/or received by the offender and access to certain websites, including his online TAFE course, were used on the device.

Count 3 - Fail to comply with interim supervision order (condition 33 - use other name)

Count 4 - Fail to comply with interim supervision order (condition 34 - not declare email address)

1. In the early stages of his interim supervision order, the offender expressed his intention to engage in helicopter lessons. At the time, the offender was subject to providing weekly schedules of his movement and any requested activities required approval from Community Corrections. The offender provided a Community Corrections officer with a contact number for Anthony Winter whom he claimed was his flight instructor from "Rotary Aviation". The Community Corrections officer made numerous attempts to contact Anthony Winter on the number provided.
2. On 7 May 2020, the email address rotarywing.aviation@gmail.com with the name "Anthony Winter" was set up from a device of the offender. Shortly afterwards, a Community Corrections officer sent an email to that address attempting to confirm the offender's helicopter lessons after the email address was provided to him.
3. On 7 May 2020, an email was sent from that address confirming the offender's flight lessons for 10 May 2020 and 15 May 2020 and was signed off by "Anthony". The offender was the person using the relevant email address and had falsely represented himself as being the person Anthony Winter.

Count 5 - Fail to comply with extended supervision order (condition 17 - not declare email address)

Count 6 - Fail to comply with extended supervision order (condition 24 - use other name)

Count 7 - Fail to comply with extended supervision order (condition 16 - use social network account)

1. The offender failed to declare six email addresses (Count 5), used ten names other than his own name (Count 6), used four social media accounts without notifying his DSO of any usernames or passwords (Count 7).
2. The failure to comply with the relevant conditions of his extended supervision order were as follows:
3. An email account clpilot6969@gmail.com with the associated name TWAIDIAPIYC was noted be signed in on the Apple iPhone X that was seized by police. This Google account was noted to be linked to the following accounts: 1. Service NSW; 2. MyGov; 3. LinkedIn; 4. YouTube; and 5. Apple ID
4. An emailed signed off "Simon" was last sent from this account on 8 July 2020. The email account elpilotomd500@gmail.com with the associated name "Simon Lowe" was noted to be signed in on the Apple iPhone X. This account was noted to be linked to the following accounts: 1. LinkedIn; and 2. Apple ID
5. Several emails were marked as read since the time the offender had been subject to his extended supervision order.
6. The email account beyondvertical90@gmail.com with the associated name "S J White" was noted to be signed in on and used by the Apple iPhone X and MacBook laptop. This account was noted to be linked to the following accounts: 1. Plenty of Fish; 2. Match.com; 3. TAFE NSW; and 4. Seek.com.au
7. This email account was used consistently since the time the offender had been subject to his extended supervision order.
8. The email account 2020home.email@gmail.com with Langley's name being noted to be signed in and used by all three mobile devices seized, as well as the MacBook.
9. Within the Gmail app on the iPhone X, all inboxes were noted to be selected with all of the above emails logged in as well as rotarywing.aviation@gmail.com with the account name "Anthony Winter" and 2020ourhome.email@gmail.com with the account name "Simon Monteiro".
10. The login details for a Facebook account were located within the password section of the Apple iPhone X. Subsequent checks identify that the Facebook page is associated with the account "Sean White" and this account is linked to a mobile phone number 0423796047, being the Optus service number associated with the Apple iPhone X. From the data available, this account was last logged in from an Optus IP address on 18 July 2020. Since being subject to the interim supervision order and the extended supervision order, the account has conducted at least 80 searches with the name of at least one Community Corrections New South Wales female staff member included in that search.
11. The Facebook application was noted to be installed on the Optus X handset, being the only declared device of the offender. The offender had not declared this account nor had he deactivated it.
12. Subsequent checks identified an active Instagram account linked to the above Facebook account. The name associated with the account is "Twadiap" which is the same name used for one of the offender's email accounts. A previous name linked to the account is "Seann White". This account is linked to a mobile phone number being the Optus service associated with the Apple iPhone X. From data available, this account was last logged in from an Apple iPhone on 10 July 2020. The account is followed by 25 users and is following 236 users. The offender had not declared this account nor had he deactivated it.
13. The application WhatsApp was installed on the Apple iPhone X. This application is a cross platform messaging service owned by Facebook. It allows users to send encrypted text messages and voice messages, make voice and video calls and share images, documents, user locations and other media.
14. An active WhatsApp account belonging to the offender had been identified. The name associated with the account is the offender's partner Carol Langley and the phone number linked to the account was 0423796047. From data available, this account was regularly being used by the offender who had not declared this account, nor had he deactivated it and uninstalled it from his device.
15. The application 'Line' was noted to be installed on the Apple iPhone X. This is a freeware application for instant communications on electronic devices such as smartphones, tablet computers and personal computers. Line users exchange text, image, video and audio and conduct free VoIP conversations and video conferences. An active Line account of the offender was identified. The name associated with the account was "Simon White" and the phone number linked to the account was 0423796047. From the data available, it appeared the account was last used on 7 August 2020. The offender had not declared this account, nor had he deactivated and/or uninstalled it from a device he regularly used.

Count 8 - Fail to comply with extended supervision order (condition 13 - employment)

Count 6 - Fail to comply with extended supervision order (condition 24 - use another name)

1. During the arrest of the offender, an amount of cash was located within his vehicle. Further, many torches were seen within the vehicle. At the time, the offender asserted that the money and torches belonged to his partner for her torch business.
2. As a result of the electronic examination conducted on the seized mobile phones, it was established that the offender was the principle facilitator involved with the purchasing, advertising, and distribution of torches. Police have identified the source from which the offender was purchasing the torches. Information provided to police identified that the offender initially contacted the company about one to two months prior, providing the name "Simon Lowe". Then offender told the company he had a partnership with Canon Australia and could organise some photography for them and further, organise film shoots from a helicopter. This never eventuated however, the offender began to purchase expensive torches at a wholesale price and was given several expensive sample torches for advertising.
3. The offender on sold these torches by various means including online via Gumtree and/or by attending several businesses. On one such occasion being 12 August 2020, the offender travelled to Komatsu located at Tomago, New South Wales. The offender provided a demonstration of the torch products he was selling and he in turn made several sales. On this occasion, the offender provided a business card for which he claimed was a marketing concept, "Into the Light" which listed 0435237201 and the email address beyondvertical90@gmail.com as his contact details.
4. Further, as a result of the electronic examination conducted, police located a spreadsheet listing the sales and profits made as a result of the torch business. Over 20 persons are noted as having purchased torches with a noted profit of approximately $1,260 between 30 June 2020 and 12 August 2020.

Count 5 - Fail to comply with extended supervision order (condition 17 - not declare email address)

Count 6 - Fail to comply with extended supervision order (condition 24 - use other name)

Count 9 - Fail to comply with extended supervision order (condition 23 - Gumtree account and email address - tonywinter638@gmail.com) (Form 1 offence)

1. The application Gumtree was installed on the Apple iPhone X. Enquiries conducted with Gumtree identified two accounts linked to a phone number of the offender. The first account is linked to the email address beyondvertical90@gmail.com with the contact name "SJ" and the above service of the offender listed as the contact number. This account has been active since 2019 and currently has no active ads.
2. On 10 July 2020, an advertisement was placed via this account for a torch for $350. On this date, a private message was sent via Gumtree to the offender asking for an email contact. The offender provided the email address rotarywing.aviation@gmail.com and commenced negotiations for the sale of the torch.
3. The second account linked to the Gumtree account is tonywinter238@gmail.com with the contact name "Tony" and the above service of the offender listed as the contact number. Records of this email being accessed by the seized MacBook computer have been located. This Gumtree account has been active since 2020 and currently has no active ads. Between 31 July 2020 and 1 August 2020, five advertisements were placed using this account, all for various torches ranging from $139 to $269.
4. Those facts clearly disclose serious objective criminality in circumstances where the offender's deliberate failure to comply with specific terms of the interim supervision order and the extended supervision order essentially meant that his supervision was significantly nullified. Interim supervision orders and extended supervision orders are only utilised where a court is satisfied to a high degree of probability that the offender poses an unacceptable risk of committing another serious offence if not kept under supervision. The law mandates compliance with such orders to ensure the safety of the community.
5. In State of New South Wales v McQuilton (Final) [2019] NSWSC 265, Fagan J observed as follows in relation to offences of failing to comply with supervision orders at [91]: "The offence created by s 12, of breaching a supervision order, is in my view intended only to provide a means of enforcement of the conditions of an order. Upon prosecution under s 12 a central purpose of punishment is to deter the defendant, specifically, against breach of the order that binds him. Prosecution and the imposition of a sentence must be directed, not exclusively but in large measure, to bringing the person who is subject to the order into compliance with its terms for the future. The supervision order in conjunction with the power to prosecute for breach is not to be viewed as a mechanism for securing preventive detention of persons who have served their sentences for past serious sex offences."
6. In addition to the need for specific deterrence, I am also satisfied that general deterrence has a role to play to promote future compliance by other individuals with both interim supervision orders and extended supervision orders.

Assessment of objective seriousness

1. In assessing the objective seriousness of Count 1, I have taken into account the following factors: 1. The nature of the breach of the interim supervision order being that the offender had not declared two phones and one laptop, an Apple MacBook. 2. The period of the offending was between 30 April 2020 and 6 July 2020 a period of two months and one week. The offender during that period had sent and received emails and text messages on each of these devices. 3. On 6 April 2020, the offender had told a Community Corrections officer that he had no relevant devices other than the one phone that he had provided information about.
2. In assessing the objective seriousness of Count 2, I have taken into account the following factors: 1. The nature of the breach was that the offender had not declared his laptop, the Apple MacBook, during the terms of the extended supervision order. 2. The period of the offending was between 5 July 2020 and 19 August 2020, approximately six weeks. The offender had been using this device during that time. 3. The offender had told a Community Corrections officer that he had no devices other than his phone.
3. The gravamen of each of these offences is that it prevents inspection of these devices for the purpose of monitoring compliance with the extended supervision order. Condition 22 of the extended supervision provides that: "The defendant must allow Community Corrections New South Wales to search any device that he may use". That search includes the power to inspect the device's logs in relation to text messages, emails, images, data, and any records in relation to searches or search engines that are being used. Clearly by not declaring any of these devices, Community Corrections New South Wales were not able to undertake any of that examination.
4. In relation to Count 1, I regard the objective seriousness as at the mid‑range.
5. In relation to Count 2, I regard the objective seriousness as below the mid-range.
6. In assessing the objective seriousness of Counts 3 and 4, I have taken into account the following factors: 1. That at the time of the offending the offender was required to provide a weekly schedule of his movements. 2. He used a false name and email to deliberately deceive Community Corrections New South Wales in relation to his movements. 3. Each name and email address was used between 7 May 2020 and 15 May 2020.
7. I regard the objective seriousness of each of these offences as being below the mid-range.
8. In assessing the objective seriousness of Count 5, I have taken into account the following factors: 1. The nature of the breach was using six email addresses that were not declared. 2. The duration of the offending was between 5 July 2020 and 19 August 2020. 3. On 22 July 2020, the offender had told a Community Corrections officer that he only uses one email address and had disclosed that address.
9. In assessing the objective seriousness of Count 6, I have taken into account the following factors: 1. The nature of the breach was using a name other than the offender's name. 2. The offender used ten names during the offending period between 7 July 2020 and 19 August 2020. That is a period of six weeks. 3. The offender used a combination of false names with email accounts that were not declared.
10. Again, this prevented Community Corrections New South Wales from remotely inspecting any of those email accounts used by the offender for the purpose of monitoring his compliance with the extended supervision order.
11. Condition 18 of the extended supervision order provided as follows: "The DSO (or any other person requested by the DSO) may remotely inspect any internet account used by the defendant, including the defendant's email addresses and social media accounts, in monitoring compliance with this order".
12. In relation to Count 5, I regard the objective seriousness as just below the mid‑range.
13. In relation to Count 6, I also regard the objective seriousness as just below the mid‑range.
14. In assessing the objective seriousness of Count 6, I have taken into account the following factors: 1. The nature of the breach was using four social media applications that were not declared. 2. The duration of the offending was between 5 July 2020 and 19 August 2020 a period of approximately six weeks. 3. During that time 80 searches have been conducted on a Facebook account, including the name of at least one Corrective Services New South Wales female staff member. An Instagram account was used that had 236 followers. A WhatsApp application was used, that is an encrypted service. This account was regularly used by the offender. A Line application was also located. There was no evidence in relation to how regularly this account was used by the offender.
15. On 15 July 2020, the offender had falsely represented to a Community Corrections Officer that he does not use any form of social media or dating applications, nor does he communicate using any device other than his mobile phone. The failure to declare the four social media applications meant that Corrective Services New South Wales were prevented from remotely inspecting the applications used by the offender for the purpose of monitoring his compliance with the extended supervision order (see condition 18 of the extended supervision order).
16. I assess the objective seriousness of Count 7 as being at the mid‑range.
17. In assessing the objective seriousness of Count 8, I have taken into account the following factors: 1. The nature of the breach was a failure to declare the nature and place of employment. 2. The duration of the offending was between 5 July 2020 and 19 August 2020, a period of approximately six weeks. 3. During his employment, the offender used a name and an email account that had not been declared. Again, this prevented Corrective Services New South Wales from remotely inspecting that email account for the purpose of ensuring compliance with the extended supervision order (see condition 18 of the extended supervision order).
18. In relation to Count 8, I assess the objective seriousness as being just below the mid-range.

Subjective circumstances

1. The offender is now 54 years old.
2. His adult criminal history commences in 1986 when he was dealt with for offences of trespass and use cancelled ticket. He was fined.
3. In 1987, he was dealt with for assaulting police and assault occasioning actual bodily harm. He was fined in respect of each of those matters.
4. In 1994, he was dealt with for an offence of improper use of telecommunications. He was fined.
5. In 1999, he was dealt with for offences of destroy or damage property and behaving in an offensive manner. There is no court result in relation to either of those matters.
6. In 2002, he was dealt with for an offence of supplying prohibited drug. He was sentenced to 6 months imprisonment. In that same year he was dealt with for two counts of using a listening device to record a conversation. He was sentenced to a term of imprisonment of 2 years with a non‑parole period of 9 months. He was also dealt with at the same time for two counts of publish a conversation unlawfully listened to. He was sentenced to fixed terms of 9 months.
7. In 2004, he was dealt with for an offence of stalk and intimidate and was sentenced to a s 12 suspended sentence for 12 months.
8. In 2007, he was dealt with for offences of assault occasioning actual bodily harm and common assault. He was sentenced to fixed terms of 3 months.
9. In 2009, he was dealt with for the offences to which I have already referred earlier in my remarks, the offences of larceny, aggravated sexual assault and destroy or damage property. As I have previously indicated, the total effective sentence for those matters was 12 years and 3 months with a non‑parole period of 7 years and 9 months.
10. The offender also has a Queensland criminal history. In 1991, he was dealt with for assault occasioning actual bodily harm and imprisoned for 3 weeks. In 2006, he was dealt with for possess prohibited article and imprisoned for 7 days.
11. He also has a Commonwealth criminal history. In 1994, he was dealt with for improper use of a telecommunication service and he was fined.
12. Having regard to the offender's criminal history, I am satisfied it disentitles him to the leniency on sentence that would otherwise be available to a person of good character.
13. The offender did not give evidence during the sentence proceedings. The following material was tendered on his behalf:

• Exhibit 1 - A letter under the hand of the offender, undated;
• Exhibit 2 - An affidavit of AH dated 1 June 2020;
• Exhibit 3 - An affidavit of PI dated 3 June 2020;
• Exhibit 4 - An affidavit of RL dated 1 June 2020;
• Exhibit 5 - A letter under the hand of Diane Thompson dated 16 May 2021;
• Exhibit 6 - A sleep study under the hand of Dr Marcus McMahon dated 10 February 2020;
• Exhibit 7 - A letter under the hand of Edgar Reyes Chaplain from Bathurst Correctional Centre dated 7 May 2021;
• Exhibit 8 - Certificates of completion;
• Exhibit 9 - A certificate of completion;
• Exhibit 10 - Documents in relation to the environmental film, Gigo;
• Exhibit 11 - Statutory declaration of PD dated 19 March 2020;
• Exhibit 12 - Three pages of photographs of a community garden;
• Exhibit 13 - A report of John Machlin, clinical psychologist, dated 25 May 2021;
• Exhibit 14 - A letter under the hand of JL dated 25 May 2021;
• Exhibit 15 - A letter under the hand of JM dated 27 May 2021;
• Exhibit 16 - Defence written submissions; and
• Exhibit 17 - Statistics from the Judicial Commission.

1. The offender's background is outlined in the report of John Machlin. Mr Machlin assessed the offender on 1 February 2021 and 24 May 2021 via audio visual link.
2. The offender reported that he was born in Sydney and was the youngest of three boys born of his parents' union. His father had been in the Air Force and later worked in logging and timber importing. The family lived in New Guinea when the offender was three years of age. When the offender was four years of age his mother tragically died from melanoma aged 33 years. His father raised the offender and his brothers on the Central Coast.
3. The offender reported that his father spent a lot of time at work and was "distant and inexpressive at home". He stated that his father had a couple of girlfriends and a longer term "dysfunctional" relationship with a women whom he described as emotionally abusive towards him.

Education and employment

1. The offender reported that he was educated on the Central Coast. He attended a Catholic boarding school and reported that he was "abused by priests" on multiple occasions over the course of a year when he was 11 or 12 years of age. Following this, the offender reported that he "went a bit off the rails" and spent time in a behavioural school. He reported that his "life normalised after that" and he attended Gosford High School up to Year 10.
2. He reported working in marketing and business development positions and travelling to the US and Europe where he primarily worked in the entertainment industry. He reported he has a daughter who was born to him in the United States in 2000.

Medical history

1. In relation to his medical history, the offender reported that he suffers from sleep apnoea and takes thyroid medication. I note that Exhibit 6 (the sleep apnoea study) indicates that there is a moderate obstructive sleep apnoea condition.

Psychiatric history

1. The offender reported a history of post-traumatic stress disorder as a result of the sexual abuse he suffered at boarding school. He reported giving evidence at the Royal Commission into Institutional Responses to Child Sexual Abuse and accessing a counsellor from Interrelate on a weekly to fortnightly basis over an estimated six year period.
2. Mr Machlin noted that in past psychiatric assessments the offender had been diagnosed with an antisocial and narcissistic personality disorder by Dr Eagle and that Dr Furst had identified a personality disorder with borderline narcissistic and antisocial traits. Both Dr Eagle and Dr Furst were noted to have considered that the offender had a past substance use disorder in remission.

Attitude to the offending

1. When being assessed by Mr Machlin, the offender disputed the justification for the extended supervision order and stated that those proceedings relied on "decades old evidence where charges have been withdrawn or dismissed". Mr Machlin noted that the offender gave a "rational albeit indignant account" of his breaches of the order and emphasised the practical difficulties that he encountered under its tight restrictions.
2. He reported that he used a false name and email address in circumstances where he believed that using his real name would have resulted in discrimination, exclusion or persecution given the media attention he has received. He stated that none of the breaches committed were committed with a harmful or exploitative intention. He disputed interpretations of his conduct as being nefarious and expressed concern that predictions of his future risk of offending were being based on "conjecture". He did express to Mr Machlin a willingness to abide by the conditions of the extended supervision order upon release from custody.

Current circumstances

1. In relation to his current circumstances, the offender told Mr Machlin that whilst in custody he has concerns for his physical safety and is in the special management area. He reported experiencing violence from other inmates whilst held in that area.

Future plans

1. In relation to his future plans, the offender told Mr Machlin that he plans to work for a friend in the field of workplace health and safety once he is released from custody. He said that he would also like to resume his course in project management by distance education and continuing learning to fly helicopters. He reported that he has strong support from his father, brother, aunty and friends.

Other material tendered on behalf of the offender

1. Exhibit 2 is an Affidavit of AH dated 1 June 2020. AH is a neighbour of the offender's father. He outlined the assistance provided to him by the offender who helps him on his rural property.
2. Exhibit 3 is an Affidavit of PI 3 June 2020. PI has known the offender for 20 years. In his opinion, the offender was moving in a positive way since his release from custody. I note that that Affidavit was prepared prior to the offender's current arrest.
3. Exhibit 4 is an Affidavit of RL 1 June 2020. The offender's father. The offender's father outlines that the offender assists him at his rural property almost daily. The property is located at Somersby. He describes a good relationship with the offender and it is clear that the offender has his ongoing support.
4. Exhibit 5 is a letter under the hand of Diane Thompson dated 16 May 2021. Ms Thompson has known the offender for 35 years. She met him through his brother. She remains supportive of the offender.
5. Exhibit 7 is a letter of Edgar Reyes, the Chaplain at Bathurst Correction Centre. Mr Reyes indicates that whilst at the correctional centre the offender completed the Positive Lifestyles Program in 2021.
6. Exhibit 9 is a certificate in relation to the completion of a course, Taking Charge of Your Life, which is a course conducted through the HOPE channel.
7. Exhibit 10 is documentation in relation to the outline of an environment film Gigo which I understand with which the offender is involved.
8. Exhibit 11 is a statutory declaration from Paul Douglas. Mr Douglas has provided training to the offender with respect to work, health and safety. In his statutory declaration he outlines the difficulties he encountered in trying to engage the offender in employment, and ultimately that the employment was terminated.
9. Exhibit 12 is photos of a community garden which was built by the offender since his release from custody.
10. Exhibit 14 is a letter under the hand of JL. JL is the stepbrother of the offender. He outlines that he had reconnected with the offender after his release from custody and he remains supportive of him.
11. Exhibit 15 is a letter from JM. He has known the offender for ten years. He represented him in a civil claim. In his opinion, the offender has a good understanding of his previous breaches of his extended supervision order and is not likely to repeat his offending.
12. Exhibit 1 is a letter under the hand of the offender. The offender indicates that he deeply regrets his actions and is now willing to abide by the conditions of the extended supervision order. He explains the difficulties created for him because of the extended supervision order, most particularly trying to get employment. He describes that his greatest achievement since leaving custody is the community garden that he commenced on his father's property. He outlines that his father is elderly and has been diagnosed with prostate cancer. He considers he is too old to run his rural property. When the offender was in the community, he was maintaining the property for his father.
13. In relation to his custodial circumstances, he indicates that he is in non‑association which restricts his access to places within the correctional facility. He described that most days he is locked in his cell for 23 hours a day. His sleep apnoea is not treated while in custody and he also described the courses he has completed whilst in custody.

Submissions on behalf of the parties

1. The Crown relied upon comprehensive written submissions supplemented by oral submissions. The Crown described the various breaches as deliberate and persistent, calling for strong denunciation. The Crown also submitted that general and specific deterrence had a substantial role to play in the sentencing exercise. The Crown summarised those factors relevant to the objective seriousness of each offence (see Crown written submissions at [8]). Ultimately, the Crown submitted the length of the aggregate sentence would mean that there would be no availability for any sentence other than full-time imprisonment.
2. Ms Betts of Counsel, on behalf of the offender also relied on comprehensive written submissions, supplemented by further oral submissions. Ms Betts submitted that the offending falls at the very lowest end of objective seriousness, as the breaches are administrative and technical in nature, with no criminal offending and no danger to the community. It was submitted that the Court would find the offender's prospects of rehabilitation as favourable and also that he is unlikely to reoffend and that he is genuinely remorseful.
3. It was further submitted that the Court should take into account the offender's hardship in custody as a result of his medical conditions and the manner of his detention. It was further submitted there is exceptional hardship to the offender's father because of the offender's incarceration. Ultimately, it was submitted on behalf of the offender, that the time spent in custody since 18 August 2020 is sufficient to address the purposes of sentencing. Alternatively, the Court could consider an alternative to full-time imprisonment, namely a community correction order or an intensive correction order.

Relevance of custodial conditions

1. Having regard to the offender's medical conditions namely sleep apnoea and severe ear pain exacerbated by cold climatic conditions, I am satisfied that custody is more onerous for the offender. I propose to moderate the otherwise appropriate sentences accordingly.

Hardship to third parties

1. Whilst I accept that the offender's incarceration will have a detrimental effect on his father in circumstances where the offender assists his father in maintenance of his property and his father has recently been diagnosed with prostate cancer, I am not satisfied that such matters warrant a finding of exceptional hardship as that term is understood as a matter of law (see R v Edwards (1996) 90 A Crim R 510 at 515). Whilst I do not regard such evidence as demonstrating exceptional hardship, I will nevertheless take it into account on sentence.

The relevance of the offender's mental health

1. The relevant principles in relation to the relevance of an offender's mental health on determining the appropriate sentence are well established and well-known (Director of Public Prosecutions (Cth) v De La Rosa (2010) 205 A Crim R 1; NSWCCA 194 at [177]). It was submitted on behalf of the offender that the offender's moral culpability is reduced due to his post-traumatic stress disorder in circumstances where this would have affected his ability to deal with the stress of strict supervision orders and requirements placed upon him.
2. In the absence of any expert evidence to establish a causal link between the offending and the offender's mental condition, I do not propose to find that such a condition warrants a reduction in moral culpability. I do, however, propose to take it into account on the basis it will make his custody more onerous.

Remorse

1. The offender has expressed remorse for his offending in the letter he wrote to the Court. I give those expressions of remorse limited weight given that they were not on oath (see Imbornone v R [2017] NSWCCA 144 per Wilson J at [57]).

Prospects of rehabilitation

1. Any view of the offender's prospects of rehabilitation must necessarily be very guarded, having regard to the risk assessment undertaken during the extended supervision order hearing and his previous response to supervision being considered poor (see the Sentencing Assessment Report (Exhibit A)). The Court is hopeful that the offender does maintain his current expressed intention to comply with the conditions of the extended supervision order upon his release from custody. It is positive that he is making future plans and is supported by family. At this stage, I am unable to find that he is unlikely to reoffend.

Form 1 matter

1. In sentencing the offender I have taken into account the Form 1 matter in accordance with the principles enunciated in Attorney-General's Application under s 37 of the Crimes (Sentencing Procedure) Act 1999 No 1 of 2002 (2002) 56 NSWLR 146.

Totality

1. In circumstances where I am dealing with the offender for more than one offence I am required to determine each sentence and thereafter consider the principle of totality. The relevant sentencing principle to consider is whether the sentence for one offence can comprehend and reflect the criminality of the other. If so, the sentences should be concurrent, but if not there should be some accumulation (see Cahyadi v R (2007) 168 A Crim R 41; NSWCCA 1).
2. In circumstances where there is some factual commonality between Counts 1, 2 and Sequence 3 on the 166 certificate, I propose to find a significant degree of concurrency between these offences. Counts 3 and 4 relate to the same event, that is, the offender using a false name and email address claiming to be a flight instructor. Again, there will be a significant amount of concurrency between these offences.
3. Count 6 and Sequences 1 and 2 on the s 166 certificate relate to the use of false names. Again, there will be significant concurrency between these counts. I note that the concurrency will be notional given that I propose to impose an aggregate sentence.
4. In relation to the remainder of the counts there will be some partial accumulation to properly reflect the nature and extent of the total criminality.

Special circumstances

1. It was submitted on behalf of the offender that the Court would find special circumstances and vary the statutory ratio between the non‑parole period and the parole period pursuant to s 44(2B), Crimes (Sentencing Procedure) Act. It was submitted that special circumstances could be found having regard to the following: 1. The offender has good prospects of rehabilitation; 2. He has taken steps to rehabilitate himself in custody; 3. The accumulation of sentence; and 4. The Court may find he has become institutionalised.
2. In circumstances where I cannot be satisfied that the offender would benefit from extended supervision and where any accumulation will be notional (given that I will impose an aggregate sentence) and further, where I am not satisfied the length of the sentence is such that he has become institutionalised, I do not propose to vary the statutory ratio.

Determination

1. In determining the appropriate sentences I have had regard to the purposes of sentencing set out in s 3A, Crimes (Sentencing Procedure) Act 1999 (NSW).
2. Having considered all possible alternatives, I am satisfied in respect of each offence that no penalty other imprisonment is appropriate pursuant to s 5(1), Crimes (Sentencing Procedure) Act. I have had regard to the objective gravity of each offence, the relevant prescribed maximum penalty and the offender's subjective circumstances.
3. I propose to impose an aggregate sentence pursuant to s 53A(1), Crimes (Sentencing Procedure) Act.
4. Pursuant to s 53A(2)(b), Crimes (Sentencing Procedure) Act the indicative terms are as follows:

• Count 1 - A starting term of 16 months discounted by 10% leaving a term of 1 year and 2 months.
• Count 2 - A starting term of 12 months discounted by 10% leaving a total term of 10 months.
• Count 3 - A starting term of 12 months discounted by 10% leaving a total term of 10 months.
• Count 4 - A starting term of 12 months discounted by 10% leaving a total term of 10 months.
• Count 5 - A starting term of 14 months discounted by 10% leaving a total term of 1 year.
• Count 6 - A starting term of 14 months discounted by 10% for the plea of guilty leaving a total term of 1 year.
• Count 7 - A starting term of 16 months discounted by 10% leaving a total term of 1 year and 2 months.
• Count 8 (taking into account the Form 1 matter) - A starting term of 14 months discounted by 10% leaving a total term of 1 year.

Section 166 certificate offences:

• Sequence 1 - A starting term of four months discounted by 25% for the plea of guilty leaving a total term of 3 months.
• Sequence 2 - A starting term of four months discounted by 25% for the plea of guilty, leaving a total term of 3 months.
• Sequence 3 - A starting term of 16 months discounted by 25% for the plea of guilty leaving a total term of 12 months.

1. Having regard to the indicative terms, I regard the appropriate total aggregate sentence as being a term of 2 years and 8 months. I have considered whether it is appropriate that that term of imprisonment or the remainder of it be served by way of an intensive correction order.
2. When determining whether to impose an intensive correction order, the Court is required to consider s 66, Crimes (Sentencing Procedure) Act. Section 66(1) requires that community safety must be the paramount consideration when a sentencing court is deciding whether to make an intensive correction order in relation to an offender.
3. Section 66(2) requires the court to assess whether making the order or serving the sentence by way of full-time detention is more likely to address the offender's risk of re-offending.
4. Section 66(3) requires the Court, when deciding whether to make an intensive correction order, to take into account the provisions of s 3A that the purposes of sentencing and any other relevant common law sentencing principles.
5. Having considered s 66 (2), I am not satisfied that serving the sentence by way of an intensive correction order is more likely to address the offender's risk of re-offending, in circumstances where to date he has declined to engage in any rehabilitation. Further, even if I was satisfied that the risk of re-offending would be better addressed by way of an intensive correction order, in my view, only a full-time custodial sentence is appropriate to address the need for both specific and general deterrence.
6. Accordingly, my formal orders are as follows.
7. Mr Monteiro in relation to each of the offences you are convicted.
8. I sentence you to a total aggregate sentence of two years and eight months to date from 18 August 2020 and expire on 17 April 2023 with a non-parole period of two years to date from 18 August 2020 and expire on 17 August 2022.
9. I direct your release to parole on 17 August 2022. I have declined to find special circumstances.

DISCLAIMER - Every effort has been made to comply with suppression orders or statutory provisions prohibiting publication that may apply to this judgment or decision. The onus remains on any person using material in the judgment or decision to ensure that the intended use of that material does not breach any such order or provision. Further enquiries may be directed to the Registry of the Court or Tribunal in which it was generated. Decision last updated: 23 July 2021