State of New South Wales v Wilmot

1. [1]

   Wayne Wilmot (the defendant) is a 53 year old recidivist sexual offender who, since 2019, has been the subject of multiple successful applications by the State of New South Wales (the plaintiff), to either detain or supervise him following the completion of his sentences.

2. [2]

   The latest application, which is the subject of this judgment, is an application by way of summons filed on 27 August 2025, for a continuing detention order (CDO) of 12 months duration under the Crimes (High Risk Offenders) Act 2006 (NSW) (the Act). As alternative relief, the plaintiff seeks a 5 year extended supervision order (ESO). Further relief seeking a 5 year ESO following the expiration of the CDO (if imposed) was not ultimately pressed.

3. [3]

   The defendant does not oppose the imposition of a 5 year ESO (including a line-of-sight condition) but does oppose the imposition of the CDO.

4. [4]

   By way of brief background, on 24 September 2019, Lonergan J imposed the first CDO on the defendant for a period of two years: State of New South Wales v Wilmot (Final) [2019] NSWSC 1276. On 7 June 2023, Lonergan J made a further CDO on the defendant for one year, expiring on 9 June 2024: State of New South Wales v Wilmot (Final) [2023] NSWSC 605.

5. [5]

   On 5 March 2024, the plaintiff applied to this Court for an ESO in respect of the defendant for a period of 5 years. On 5 April 2024, following a preliminary hearing, Wilson J imposed an interim supervision order (ISO) on the defendant: State of New South Wales v Wilmot (Preliminary) [2024] NSWSC 354. On 9 June 2024, the CDO imposed by Lonergan J expired, and the defendant was released from custody subject to the terms of the ISO.

6. [6]

   Less than a fortnight after his release, on 21 June 2024, the defendant was arrested and charged with failing to comply with the ISO contrary to s 12 of the Act. For this ISO breach offending (set out in more detail below) he was returned to custody, and on 30 July 2024, he was sentenced in the Local Court of NSW to a fixed term of 18 months (expiring on 20 December 2025), later affirmed by the District Court on 18 September 2024, following an unsuccessful severity appeal. Following the defendant’s return to custody, the plaintiff, with the consent of the defendant, withdrew its application for an ESO dated 5 March 2024.

7. [7]

   The defendant is currently subject to an interim detention order (IDO) made by Fagan J which took effect at the expiration of the defendant’s sentence on 20 December 2025. The IDO has been extended a number of times and will finally expire on 20 March 2026.

8. [8]

   I have determined that the defendant should be subject to a CDO for one year. I now set out the reasons for my decision.

General Background

1. [9]

   The defendant was born in March 1973 and suffered from an extremely dysfunctional upbringing, marked by neglect, abuse, inconsistency of caregivers and general instability. He was made a ward of the State at the age of five, in 1979. He was placed at different times in foster care, children’s homes, refuges, juvenile detention institutions and other institutions. He ran away from a number of placements and was sexually abused during this time. There were a number of failed attempts at restoration with his mother.

2. [10]

   The defendant commenced abusing substances at the age of eight. While living on the street he abused alcohol, cannabis, Lysergic acid diethylamide, amphetamines and benzodiazepines. He reported ceasing substance abuse following his release from custody in 1996 and has denied further substance use since then.

3. [11]

   The defendant has been diagnosed with a polysubstance use disorder, in remission in a controlled environment, as well as a Severe Personality Disorder. He also satisfies criteria for Antisocial Personality Disorder and Borderline Personality Disorder. His cognitive functioning is assessed as falling into the borderline range, and he does not satisfy the criteria for an intellectual disability.

Criminal history

1. [12]

   The defendant’s criminal history started at 13 years of age with stealing offences.

2. [13]

   His first recorded sexual offence occurred in January 1987, when at the age of 13, he attacked an adult female victim walking through a park. When apprehended he was reported to have said “I’ve got a problem” and “this is not the first time I’ve done this”. He was convicted of sexual assault and related charges and committed to an institution.

3. [14]

   On 19 July 1987, aged 14, the defendant assaulted and robbed another adult female victim, exposing his penis and stealing her handbag. He was convicted of assault and rob and sentenced to a 2 year control order. He was also charged with wilful and obscene exposure which was dealt with in the sentencing for the offence set out in the next paragraph.

4. [15]

   One day later, on 20 July 1987, the defendant indecently assaulted a further adult female victim, who was pushing a pram containing her 18-month-old child. For this offence, and in relation to the wilful and obscene exposure referred to above, he was made subject to a 2 year probation order.

5. [16]

   On 8 September 1988, aged 15, the defendant and a female co-offender and male co-offenders travelled to Sutherland Railway Station with a plan to randomly abduct a woman to sexually assault her. The male co-offenders abducted a woman at knifepoint and the defendant drove the car while the victim was sexually assaulted in the backseat. The defendant stopped the car at an isolated stop on a freeway and remained in the car as the victim was removed from the car, sexually assaulted, bound, gagged, thrown over a fence, dragged to, and held underwater in, a dam until she drowned. This was done by the male co-offenders without the defendant’s involvement. Some of the victim’s personal items were shared and her ATM card used to withdraw money later that day. The defendant was taken into custody on 10 September 1988. On 22 March 1990, he was convicted of abduction and sexual intercourse without consent (four counts), robbery in company, and receiving and obtaining financial advantage by deception. He was sentenced to a total term of imprisonment of 9 years and 4 months, with a 7 year non-parole period. This sexual offending is a serious sex offence as defined in s 5(1)(c1) of the Act.

6. [17]

   The defendant was released to parole on 16 October 1996 and spent 20 months in the community. During that period, the defendant offended on four further occasions:

7. [18]

   The defendant was returned to custody as result of this series of crimes and he remained there until his release on the ISO in 2024.

8. [19]

   Whilst in custody, the defendant was also convicted of sexual assault and assault with act of indecency against two other prisoners. He received a sentence of five years, with a non-parole period of three years and nine months commencing on 27 June 2014, expiring on 26 June 2019.

9. [20]

   The defendant was also charged with a range of other sexual offences in 2011, 2022 and 2023, but the matters either did not proceed or the defendant was found not guilty. The allegations underpinning these charges were made by inmates in custody with the defendant.

Recent offending and return to custody

1. [21]

   After the defendant was released subject to the ISO on 9 June 2024, the following took place:

2. [22]

   As noted above, on 21 June 2024, the defendant was arrested and charged with one count of failing to comply with the ISO for searching for and viewing restricted X18+ material without approval.

3. [23]

   Following the defendant’s return to custody, the defendant’s cellmate reported being sexually assaulted by the defendant between 21 and 25 June 2024. The allegations included that the defendant had forced two fingers into the cellmate’s anus and made him perform oral sex on the defendant. The defendant denied the allegations and the complainant confirmed he did not wish to proceed with the matter due to concerns about retribution.

4. [24]

   The defendant has also incurred institutional charges whilst in custody, including intimidation, possess prohibited weapons and assault.

5. [25]

   The most recent assault allegation is that on 4 November 2025, the defendant assaulted another inmate by headbutting and hitting the inmate to his head with his right hand. The incident was captured on CCTV footage which I have viewed.

Hearing before me

1. [26]

   The hearing was held on 5 March 2026. A large volume of written material was tendered and a number of witnesses were called. Written and oral submissions were made and the Court is grateful for the assistance provided by Mr Babb SC who appeared with Ms Richards for the plaintiff, and Mr Broadbent SC who appeared with Mr Bhutani for the defendant, as well as their instructing solicitors.

2. [27]

   The plaintiff relied upon affidavits from Ellen Southwood, Briony O’Loughlin, Kelli Grabham, Sharryn Coe, Liam Matson, and Vicki McCarthy. Four witnesses were called to give evidence: Sharryn Coe, the Director of the Intensive Rehabilitation Directorate; Sarah Wright, the author of Risk Assessment Reports (RARs); and the two court-appointed experts who provided reports, Dr Sathish Dayalan (Psychiatrist) and Mr Patrick Sheehan (Psychologist).

3. [28]

   Also placed before the Court by the plaintiff was a statement of a victim of the defendant’s offending in accordance with s 21A(4) of the Act. The statement was provided to the court with the identity of the maker redacted. That set out the serious and lifelong effect the defendant’s offending has had on the victim. The Court is grateful to have heard directly from one of the defendant’s victims.

4. [29]

   The only live issue before me at the hearing was whether the defendant should be subject to a CDO (which involved exploration of the details of the Reintegration External Leave Plan (RELP), discussed below), or whether he should be placed on an ESO with conditions, including line-of-sight supervision. It was conceded that the statutory preconditions were otherwise satisfied for the making of both a CDO and an ESO.

Evidence in relation to the Reintegration External Leave Plan (RELP),

1. [30]

   As noted, Ms Coe is the Director of the Intensive Rehabilitation Directorate. As set out in her affidavit and oral evidence, since October 2025, a multi-disciplinary team has been meeting weekly to assist in the preparation of the Defendant’s eventual release to the community. A central part of this planning is the RELP. The RELP is designed to address the defendant’s individual reintegration needs while managing risk to the community. This allows the ESO team to engage the defendant in a wide range of activities while he is still in custody. Importantly, it is aimed at supporting his reintegration by gradually increasing his exposure to the community.

2. [31]

   It can also be noted that on 11 June 2025, the National Disability Insurance Scheme (NDIS) approved a 12 month plan for the defendant in the amount of $221,620.99 with the funding to be reviewed annually. The plan sets out the support the defendant will received until 10 June 2026.

3. [32]

   The defendant’s accommodation following custody has been arranged at the Nunyara Community Offender Support Program (COSP). This facility is fenced and is staffed 24 hours a day seven days a week. It has a curfew and is locked at night to prevent unauthorised persons accessing the facility at night. There are security cameras monitoring the COSP 24 hours a day. Whilst ordinarily designed as transitional accommodation with a six-month limit, there is greater flexibility for high needs inmates subject to an ESO. Accordingly, there is no fixed time limit for the defendant’s time in the COSP.

4. [33]

   Ms Coe stated that the first RELP for the defendant was approved on 23 October 2025.

5. [34]

   Ms Coe noted an incident which occurred on 4 November 2025 (noted above at [25]) when the defendant acted aggressively and assaulted another inmate. As a result of this incident, the defendant was segregated for 7 days and his external day leave schedule was impacted, with his first period of external day leave delayed until 4 December 2025.

6. [35]

   By the time of the hearing, the defendant had completed thirteen external leave days, with generally positive performance. The activities the defendant has undertaken to date include him obtaining a temporary Medicare card, attempting and later successfully completing banking arrangements, undertaking basic phone setup tasks including SIM activation and account creation. He has also purchased basic organisational items, such as a folder and diary to help him manage his appointments and important documents. He has also attended health appointments including a GP consultation, a psychology session with Dr Carollyne Youseff, and a psychiatry review at Justice Health NSW Treatment and Rehabilitation Clinic (TRC) during which he has remained cooperative and behaved appropriately.

7. [36]

   The defendant has also accessed the disability support service, Mates & Mentors, funded through the NDIS, during his external day leave on 21 January 2026. The NDIS can provide a maximum of four hours of support per day for assistance with social economic and community participation, seven days per week (subject to changes in the NDIS plan, or his circumstances on release). Ms Coe stated that the approval for flexible use of core supports enables a staged transition to the community while allowing support staff to attend initial training regarding the defendant and gradually build rapport with the defendant as he adapts to independent living, with ongoing support needs to be addressed if he is released into the community.

8. [37]

   Since the incident on 4 November 2025, the defendant lost his employment in the kitchen. Following his seven-day segregation, the defendant was trialled in new roles and is now employed in the laundry.

9. [38]

   The defendant has an allocated room at the COSP and has been accessing this room at the beginning of each external day leave and sometimes at the end. He sometimes has lunch at the COSP and has the opportunity to engage with other residents.

10. [39]

    Ms Coe also provided evidence about an incident on 19 February 2026 at the Nunyara COSP whilst on external day leave. It occurred in the context of the defendant having a discussion regarding his NDIS support with his two DSOs after they had returned to the COSP following attending to earlier activities in the community together. Of particular concern was that the incident appeared to escalate quickly with no identifiable trigger; it involved behaviour reported by the DSO to be “extremely heightened” and “verbally aggressive” and raised questions about the defendant’s ability to deal appropriately with such frustration or disagreements in the community.

11. [40]

    As a consequence of the 19 February 2026 incident, the defendant’s external day leave planned for 23 February 2026 was suspended to allow time for a formal debrief with the defendant and those associated with his care. A “structured response” was developed and then undertaken, including a debrief with the Centre Governor (on 20 February 2026), psychological intervention by Dr Richard Parker, the CSNSW Specialist Senior Psychologist, and an interview between the DSO and Team Leader with the defendant to revisit the incident, clarify acceptable behaviour and explore triggers, and monitor the defendant in custody.

12. [41]

    Also on 19 February 2026 but prior to the above incident, the officers accompanying the defendant on external day leave observed two episodes where the defendant exhibited inappropriate interest in women in his presence at a medical centre and a shopping centre.

13. [42]

    External day leave resumed on 26 February 2026, and it progressed positively with no further incidents or inappropriate behaviour.

14. [43]

    Ms Coe stated that the RELP would continue to be reviewed should a CDO be ordered. Progression to three days of external day leave per week would be dependent on the defendant’s continued progress and resources. Ms Coe stated if the defendant regresses or there is otherwise behaviour of concern, external day leave may again be paused or reduced as appropriate.

15. [44]

    Ms Coe further stated that if the defendant were granted external overnight leave at the COSP he would also be required to wear electronic monitoring equipment and would be subject to a curfew. Ms Coe stated that external overnight leave would provide:

16. [45]

    At the hearing, Ms Coe informed the Court that an updated RELP had been approved the day before the hearing. Importantly, the updated RELP provides for up to three days supervised external day leave as well as the possibility of overnight stays. Whilst the overnight stays would not necessarily be available immediately, the RELP provides the capacity for a staged process such that overnight stays can be introduced when the defendant is deemed stable enough for them.

17. [46]

    Ms Coe outlined that, to date, whilst on the current IDO, the defendant has been on external day leave two times a week for a period of five hours on each occasion, with the plan to increase that up to three days a week, reflective of the resources of the team. Each external day leave requires two staff members to accompany the defendant on each occasion. Similarly, if a line-of-sight condition was a condition of an ESO, two departmental officers would be required each time the defendant wished to leave the COSP where he would reside. If the defendant were on an ESO, no more than three accompanied outings a week would be available, and the team could only commit to the first six weeks of the ESO. Ms Coe stated that given resourcing, after six weeks, her team would be “taking the opportunity to see what opportunities there were to transition him to a lesser level of supervision”. Beyond those six weeks, it would be “very difficult” for her to resource and commit to line-of-sight supervision. On the other hand, if the defendant was on a CDO, the defendant must necessarily be accompanied by corrections staff at all times when he is on external day leave.

18. [47]

    Ms Coe stated that on an IDO or CDO, increasing to three days of supervised external day leave as well as progressing to overnight leave is dependent on the defendant’s progress as well as resourcing.

19. [48]

    Ms Coe helpfully summarised the main differences between a CDO and an ESO. She stated if the defendant is on a CDO and is out on escorted day leave, and there is an incident where people are feeling unsafe or there is a risk to community safety as a result of the defendant’s conduct a decision can be made to return him to custody immediately. In contrast, if he were on an ESO, they would need to respond within the conditions of the order, and it is likely that he would remain restricted to his accommodation location, where he would have access to staff and other residents.

20. [49]

    Further, as stated in Ms Coe’s affidavit of 3 March 2026, if the behaviour constituted a breach of his ESO, breach-management processes may be initiated, which may include further charges.

21. [50]

    Ms Coe also stated in that affidavit that, if subject to a CDO, external day leave could be structured such that when at the COSP the defendant is always supervised by a DSO. Under an ESO with a line-of-sight condition, the default is rather that the defendant would remain at the COSP at all times unless with a DSO. There would be no physical barrier preventing the defendant from leaving the COSP from 6am to 9pm (when the COSP is unlocked).

22. [51]

    Further, if the defendant were to leave the COSP without approval there would be differences in responses depending on whether he was subject to an ESO or a CDO. Under an ESO, leaving the COSP without approval would be treated as a breach of the ESO and breach-management processes would be initiated. Under a CDO, if he were at the COSP on external day leave, he would remain a person temporarily released from lawful custody. Leaving the premises without authority or failing to return at the end of the approved leave period would be considered an escape from lawful custody and police would be called.

23. [52]

    At the hearing, Ms Coe stated that the handling of the 19 February incident showed how the RELP was serving its purpose and it highlighted how it was able to be responsive to emerging risk. She stated:

24. [53]

    Ms Coe returned to update her evidence after the luncheon adjournment and said that depending upon the demonstrated compliance and cooperation with overnight leave, it may be possible to further amend the RELP and extend the length of overnight leave available, up to three nights, and potentially more. Ms Coe stated, “I don’t think that anything is off the table […] but it needs to be a considered and planned approach”.

25. [54]

    Before I turn to the main issue, I will briefly set out my findings in relation to the statutory preconditions.

Statutory preconditions

1. [55]

   I am satisfied that the following statutory preconditions for the making of either a CDO (or an ESO) are satisfied. By reference to the CDO provisions, and as conceded by the defendant, I am satisfied that:

2. [56]

   The Court must also be satisfied to a high degree of probability that the offender poses an unacceptable risk of committing another serious offence if not detained: s 5C of the Act. In determining whether to make an order, the safety of the community must be the paramount consideration (s 17(2)), and the court must have regard to the matters set out in s 17(4) of the Act, in addition to any other matters it considers relevant. The s 17(4) matters are also useful in relation to applying the unacceptable risk test: State of New South Wales v Davis (Preliminary) [2020] NSWSC 754 at [28].

3. [57]

   Section 5D of the Act provides:

4. [58]

   The meaning of unacceptable risk is not defined in the Act. Its meaning was considered by Beazley P in Lynn v State of New South Wales (2016) 91 NSWLR 636; [2016] NSWCA 57 at [50]-[51] (Lynn) in the context of an application for an ESO (but is equally relevant to an application for a CDO):

5. [59]

   In Lynn, Basten JA stated at [126]:

6. [60]

   The unacceptable risk inquiry is not discretionary, but it does involve an evaluative balancing exercise to be undertaken in the overall context of the primary object of the Act, that being to ensure the safety and protection of the community: s 3(1) of the Act. Unacceptability of risk involves consideration of both the likelihood of the risk eventuating and the gravity of the risk that may eventuate: State of New South Wales v Simcock (Final) [2016] NSWSC 1805 at [71] (Wilson J); and State of New South Wales v Chaplin [2019] NSWSC 471 at [15] (Rothman J).

7. [61]

   An offender may pose an unacceptable risk even where the likelihood of committing another serious offence is low if the likely consequences of such an offence are very grave: State of New South Wales v Kamm (Final) [2016] NSWSC 1 at [41] and [43] (Harrison J); and State of New South Wales v Devaney (Final) [2022] NSWSC 60 at [73] (Dhanji J).

8. [62]

   I now turn to consider the matters in s 17(4) of the Act.

Section 17(4) matters

1. [63]

   Dr Dayalan was appointed as an expert at the preliminary hearing for this application and provided a report dated 9 February 2026. As noted, he also gave evidence at the hearing before me.

2. [64]

   Dr Dayalan was previously appointed by the court in April 2024 in relation to the plaintiff’s earlier application for an ESO. His first report is dated 28 May 2024. In that report, he opined that the defendant suffered from a Borderline and Antisocial Personality Disorder and a substance use disorder (in remission in a controlled environment). Dr Dayalan then considered that the defendant presented a risk of committing a further serious offence and required close supervision and monitoring if released into the community on an ESO.

3. [65]

   For his latest report, Dr Dayalan interviewed the defendant by video-link on 23 January 2026. Relying on this interview as well as other sources, after setting out some of the defendant’s background, Dr Dayalan recorded that the defendant denied having committed any sexual offences and initially claimed that he only had convictions for two sexual offences one of which he had not directly participated in, and the other one which he said was consensual. The defendant contended that his convictions for sexual offending in custody arose from false allegations. In relation to the ISO breach offending, the defendant claimed to have clicked on a “pop up” and “had a look around” because he is “only human”. He contended that he did not know that he needed permission to access pornographic material and that he had been given a phone with no instructions on how to use it. In relation to the recent assaults in custody, he said, “they were warranted” and that he could have seriously hurt the inmates but instead restrained himself.

4. [66]

   Dr Dayalan observed that the defendant’s disposition in the interview varied quite quickly, and he became agitated when discussing past behaviour of concern. Whilst maintaining he had not committed any sexual offences, he stated, “I have been trying to get it [sexual functioning] a bit more active in the last couple of weeks… as I could be getting out…. I would like to get my dick wet like any other bloke”.

5. [67]

   The defendant reported adapting well whilst on leave in the community. He acknowledged impulsivity but said he was making an effort to slow down his decision making and intended to comply with the conditions of any ESO.

6. [68]

   Dr Dayalan confirmed his earlier psychiatric diagnoses of the defendant. The defendant presented with traits which support diagnoses of Borderline and Antisocial Personality Disorder, including impulsivity, difficulty regulating anger resulting in aggression, propensity for paranoid ideation, problems with interpersonal relationships, failure to conform with social norms, deceitfulness, reckless disregard for the safety of others, lack of remorse and consistent irresponsibility.

7. [69]

   The defendant also meets diagnostic criteria for substance use disorder currently in remission (cannabis, benzodiazepines, and probably alcohol).

8. [70]

   Dr Dayalan also noted the defendant had been assessed as suffering from psychopathy, which, whilst not listed in the DSM-V, was “nevertheless quite relevant to his risk of violence and criminal offending behaviour”.

9. [71]

   The STATIC-99R risk assessment placed the defendant in the Well Above Average Risk level with a score of 9, which Dr Dayalan considers unlikely to change.

10. [72]

    The STABLE2007 test showed the defendant having a high level of stable dynamic risk and needs, with relevant dynamic risk factors such as lack of concern for others, impulsivity, poor cognitive problem solving skills and problems cooperating with supervision. Dr Dayalan observed that the defendant’s recent behaviour in the community indicates a heightened sex drive and deviancy in sexual interests.

11. [73]

    Dr Dayalan also assessed the defendant’s risk of future violence and found the defendant to have a high loading of historical risk factors, clinical risk factors and risk management variables. If released to an ESO, Dr Dayalan anticipated problems in engaging with professional services due to his antisocial personality, problems with his living situation due to likelihood of conflict and problems with response to treatment given limited insight. Dr Dayalan opined that the defendant has limited strategies to cope with stress, and being released to the community on an ESO with restrictions would likely contribute to the level of stress experienced by him.

12. [74]

    In essence, Dr Dayalan found that the defendant presents with a high loading of static and dynamic risk factors for both sexual and violent offending, with the risks long-term in nature. Importantly, Dr Dayalan stated:

13. [75]

    Dr Dayalan highlighted certain matters in his oral evidence, including that the defendant was quite institutionalised and that the last time he was out in the community he found it quite overwhelming. He recalled the defendant having reported an interaction after being out in the community that it was good for him to get back custody to allow him to get his head around things.

14. [76]

    Dr Dayalan had concerns about the defendant being subject to an ESO, including that there was an increased risk of him reacting in an aggressive manner which might continue to escalate if he were to be repeatedly exposed to an environment which he finds stressful. Further, in the context of anticipated NDIS support in the community, he referred to the report of Dr Sally McSwiggan, Consultant Neuropsychologist dated 11 November 2021, who stated:

15. [77]

    Dr Dayalan emphasised that his support for a CDO is primarily based on the premise that the defendant would have increasing amounts of leave from the correctional facility into the community which would help with his transition to the community. Dr Dayalan stated that the defendant would struggle going into the COSP on an ESO without a greater period of transition. He stated:

16. [78]

    Dr Dayalan added that if everything went well a lesser period than 12 months might be sufficient but that would depend on there being no “hiccups”.

17. [79]

    Mr Sheehan was also appointed as an expert at the preliminary hearing in the context of the present application and provided a report dated 13 February 2026. As noted, he also gave evidence at the hearing before me.

18. [80]

    Mr Sheehan had also been appointed by the court in April 2024 in relation to the plaintiff’s earlier application for an ESO. His first report is dated 24 May 2024. At that time, Mr Sheehan diagnosed the defendant with polysubstance use disorder (mild-moderate, in sustained remission in a controlled environment), and a severe personality disorder with ‘Cluster B’ presentation, being a composite of primarily Antisocial Personality Disorder but also with features of Borderline Personality and Narcissistic Personality. He assessed the defendant’s risk of a serious sex offence to be at the “high end of the risk spectrum” and that it was “very clear” that the risk could not be managed adequately in the community without an ESO. In his most recent report, Mr Sheehan confirmed the previous diagnoses. He was unable to arrive at a diagnosis of ADHD but could not exclude it, noting that, in his view, the defendant’s recent preoccupation with dexamphetamine but refusal of non-stimulant medications suggests he is more interested in seeking stimulant mediation than in addressing any symptoms.

19. [81]

    Mr Sheehan was unable to reinterview the defendant for his most recent report as the defendant failed to attend a scheduled appointment for assessment, claiming he was sick due to “dust mites”. Mr Sheehan noted however that the defendant was well enough the following day to engage in external day leave. Accordingly, Mr Sheehan’s report was based upon the material with which he was briefed as well as his 2024 interview with the defendant.

20. [82]

    After setting out the defendant’s background, Mr Sheehan opined that the nature of the defendant’s ISO breach “reveals his that his sexual interests remain strong and focussed on themes of sexual aggression and domination”.

21. [83]

    Mr Sheehan set out that in 2024, the defendant took almost no responsibility for his offence history relating to sexual violence,

22. [84]

    Mr Sheehan also noted the troubling level of sexual predation allegations in custody, the most recent in 2024.

23. [85]

    More positive, however, was the recent significant effort to ensure a coordinated multidisciplinary case management approach for the defendant’s eventual release. Mr Sheehan noted the defendant’s behaviour whilst on external day leave has been positive.

24. [86]

    Mr Sheehan’s assessment of the defendant’s risk was in essence the same as that of Dr Dayalan, also based on various risk assessment tools. He opined that the defendant’s offending is skewed heavily towards sexual crimes, but violence is embedded in his offending. He noted the following dynamic risk factors as being relevant: the chronic nature of the defendant’s sexual violence history commencing in childhood and persisting across the life span; poor psychological adjustment as reflected in denial and extreme minimisation; severe problems with self-appraisal and a range of pathological coping behaviours; sexual preoccupation and sexual coping and presence of psychopathic personality; serious problems with social adjustment through intimate and non-intimate relationships and persistent antisocial attitudes; serious problems with supervision, with the ISO breach revealing this problem is ongoing. In summary, Mr Sheehan considers the defendant is in the “highest range of the risk spectrum” for further serious sexual offending and “loads heavily” across all the established domains of dynamic risk factors.

25. [87]

    Mr Sheehan opined that the defendant’s risk scenario primarily pertains to random sexual attacks on women in public places, with offending occurring spontaneously and opportunistically, targeted by perceived vulnerability and would likely use some degree of force or violence with risk to the victim of injury of unpredictable severity. There is a possibility a weapon might be used and sexual risk to young children cannot be excluded.

26. [88]

    Mr Sheehan opined that he considers it “arguable” as to whether a CDO would “substantially add to [the defendant’s] prospects” noting the significant resources put in to readying him for release and his current momentum. He is of the view that if a CDO were to be imposed, 2 – 6 months would be “adequate for the purposes of the RELP”.

27. [89]

    In oral evidence, Mr Sheehan confirmed that he would have preferred to have been able to interview the defendant, but he still had plenty of information for his report. He agreed with Dr Dayalan that there is a lot of benefit in graduated release and referred to the plans put forward by Corrections as “a gold standard of preparation for release”.

28. [90]

    Mr Sheehan was of the view that given the extent of the defendant’s institutionalisation, there would be likely mistakes and poor judgments regardless of the type of whether he was on a CDO or ESO, and that compliance would be very difficult for him.

29. [91]

    Mr Sheehan stated that whilst it would be most desirable to have staged release before moving onto an ESO, given he has now finished his sentence, and a staged release would involve a CDO, an ESO would be “adequate”. The most “desirable” plan would have been to do the staged release whilst he was still serving a sentence, but overall, he would “never criticise what’s going on” and indeed encouraged it. Mr Sheehan’s view was that the most desirable period on a CDO was a period of two to six months. This shorter length of time would provide some “momentum” and “some personal stake in the processes that are occurring”. Because the defendant is “pretty entitled” Mr Sheehan was of the view that he would get to the point where he might be difficult to dealt with and he “might lose sight of the objective of going out to live his life in the community”.

30. [92]

    Mr Sheehan stated he was impressed with the level of responsiveness by the authorities to the defendant’s setbacks, and he had not seen that level of responsiveness before.

31. [93]

    In a question from me, Mr Sheehan agreed that embedding life skills in an institutionalised person takes a while, and then stated:

32. [94]

    Ms Wright’s RAR reports are dated 20 November 2023, 2 July 2024, 27 June 2025 and 4 March 2026 (the latter three reports being updates).

33. [95]

    During the 2023 assessment Ms Wright conducted with the defendant, he indicated he wanted to “start fresh” and “forget this system” and maintained that he did not commit any sexual offences. He did not acknowledge any risk factors, nor did he acknowledge any need to do things differently or implement strategies to not reoffend.

34. [96]

    At that time Ms Wright noted the defendant had exhibited a high level of violence and aggression towards staff and inmates, particularly when he disagreed with something, exemplified by the defendant’s own example of grabbing a psychiatrist by the throat to force him to take him off medication. He appeared to justify his behaviour by saying he was better off without that medication.

35. [97]

    Ms Wright administered a number of tests to assess the defendant’s risk of future offending, which again, essentially came to the same conclusion as the court appointed experts. For instance, combining the STABLE-2007 and STATIC-99R results generated a composite assessment of risks/needs as placing the defendant at Well Above Average risk of future sexual offending. Likewise, the defendant’s dynamic risk factors assessed by the tool RSVP V2, placed the defendant in the High Risk category for repeat sexual violence.

36. [98]

    Not only did Ms Wright opine that the defendant was at a well above average risk for further sexual offending, but she also stated he was at a high risk for violent offending. She was of the view that sexual offending was likely to be impulsive and opportunistic, may occur in the context of other offending, and would most likely involve forced penetrative sexual activity with use of physical coercion.

37. [99]

    Her more recent reports confirmed that the defendant’s risk of recidivism remains the same as noted earlier. In the July 2024 report, Ms Wright stated that the defendant’s risk scenario should be broadened to consider teenage girls as well as potentially accessing child abuse material. Further, in the June 2025 report it was noted that the defendant’s most recent convictions suggested a lack of understanding of the importance of complying with conditions and also identified potential sexual arousal to, and gratification from, sexual violence.

38. [100]

    In Ms Wright’s most recent report and in oral evidence, she stated that the therapeutic or rehabilitative benefits would be similar under either a CDO or ESO, but a CDO would provide a higher level of containment. She was of the view that there could be potential benefits to a gradual, supported transition towards independence with overnight leave under a CDO. Ms Wright said it was plausible that other residents at the COSP would be at risk, given the defendant’s history of sexual offending against inmates, and allegations of the same conduct.

39. [101]

    A great number of reports have been prepared in relation to the defendant over the years. The content of many of these reports have been summarised by Lonergan J in State of New South Wales v Wilmot (Preliminary) [2019] NSWSC 776 at [75]-[103] and State of New South Wales v Wilmot (Final) [2023] NSWSC 605 at [26]-[45] and will not be repeated here.

40. [102]

    Included amongst that material, it is worth highlighting the following.

41. [103]

    Dr Rod Milton, consultant psychiatrist, in a 1999 report, opined that the defendant was “chronically a very dangerous person” whose risk was likely to persist into the foreseeable future (decades rather than years), for whom no treatment could be offered. An environment that provided support, restrictions, limitations on his anti-social behaviour and medication was “the one likely to do the most for him”.

42. [104]

    Dr Richard Parker, in a RAR dated 17 June 2021, opined that the defendant’s psychopathic personality “means that the normal inhibitions which restrain most people from offending, and most offenders from committing certain types of offences, are not operative, or are of lesser strength”.

43. [105]

    Dr Kerri Eagle, in her report dated 5 November 2021, opined that the defendant had developed severe maladaptive personality traits which are difficult to manage or modify, and which were likely to contribute significantly to his ongoing offending risk. Dr Eagle was of the view that it was highly likely the defendant would continue to experience difficulties accepting and tolerating supervision.

44. [106]

    Further, in Dr Sally McSwiggan’s report dated 11 November 2021, she opined that the defendant was “an unremitting opportunistic offender with a disregard for potential sanctions”. Dr McSwiggan also noted that while he had previously superficially complied with Community Corrections, he reverted to serious offending within a year of his release and his behaviour in custody since suggested this pattern may well be repeated.

45. [107]

    I take into consideration the Risk Management Report (RMR) dated 20 June 2025 prepared by Ms Louise Robinson, the Acting Team Leader of the Extended Supervision Order Team, as well the evidence of Ms Coe, as discussed above and further set out below.

46. [108]

    The RMR sets out a tailored risk management plan for the defendant in the event an ESO is imposed, with a focus on both engaging in targeted intervention to address his offending and mitigate the risk of re-offending, as well as transitioning the defendant into the community given his significant institutionalisation.

47. [109]

    As set out above at [48]-[53], Ms Coe gave clear evidence outlining the differences between and ESO (with a line of sight condition) and a CDO. I was impressed by the level of responsiveness provided by Ms Coe and her team to the defendant under the IDO and which would be able to be provided under the CDO.

48. [110]

    The defendant was first enrolled in High Intensity Sex Offender Program (HISOP) in 2012. HISOP is a seven to ten month long custody-based residential therapy program for men who have committed sexual offences and who are assessed as having moderate to high-risk needs. He was suspended from this program within the first six weeks for “inappropriate and aggressive behaviour”. This included exposing his genital area to young female staff, referencing his “suck me” tattoo on his groin area, and verbally abusing a teacher and throwing a chair.

49. [111]

    The defendant re-attempted HISOP between June 2018 and June 2019. This time he was again discharged prior to completion, but it was noted that “he had likely achieved as much as he would and that he would not gain anything further from re-entering HISOP at the time. Reasons for discharge included ongoing difficulties managing aggressive behaviour, poor insight and resistance to planning for the future, limited willingness to discuss sexual offending and concerns about the ability to control his behaviour in the context of increasing agitation and aggression. These concerns are exemplified by the following extract from the HISOP treatment report dated 26 July 2019.

50. [112]

    It can also be noted that the defendant has described HISOP as “rubbish” and that he got “fuck all” out of it.

51. [113]

    The defendant has had one-on-one sessions with Dr Parker, the CSNSW psychologist, as well as with Dr Carollyne Youseff, a psychologist in the community. The defendant’s behaviour has largely been positive in these settings and has made some progress in relation to strategies for dealing with aggression. However, again, the defendant remained unwilling to talk about his sexual offending. He further blamed his breach of the ISO on external factors, including that someone brought him a “cheap phone”.

52. [114]

    Mr Sheehan noted that the defendant’s risk factors are chronic and have remained largely resistant to therapeutic intervention. He also noted that the recent sessions with Dr Parker had not revealed much by way of identifiable gains.

53. [115]

    Further, as observed by Ms Wright in the RAR dated 20 November 2023:

54. [116]

    It can also be noted that the defendant was also recently referred to the TRC of the Community Forensic Mental Health Service (a new NSW Health service, offering highly specialised assessments and treatments for patients with complex forensic mental health needs, specifically problematic sexual behaviours). On 6 January 2026, the defendant attended an appointment with Dr Kevin Bragg (Psychiatry Registrar) and Dr Andrew Ellis (Forensic Psychiatrist).

55. [117]

    Those doctors noted that the defendant focussed primarily on concerns relating to inattention which the defendant attributed to a diagnosis of ADHD and he requested stimulant medications. The doctors did not aim to specifically confirm or exclude an ADHD diagnosis, but in their opinion, his inattention could have multiple drivers in addition to or instead of ADHD. Their opinion was that, despite his denial of any problematic sexual thoughts, his history was strongly suggestive of a sexual sadism disorder and possibly a paraphilic disorder, specifically an exhibitionist disorder. They noted that the defendant was offered, and refused, libido lowering medication; and was offered and refused medical investigations to assess for the possible appropriateness of libido lowering medication.

56. [118]

    Stimulant treatment, requested by the defendant, was refused. The doctors informed the defendant that such medication was contra-indicated as it would, contrary to his assertions, almost certainly increase his libido and accordingly increase his risk of problematic sexual behaviours. It would potentially also negatively affect his physical health, especially his blood pressure and kidney health. They also stated that given his documented history of substance use disorder including recreational stimulants, prescribing stimulants would also pose a potential risk of relapse or misuse. It was further noted that the defendant refused to discuss non-stimulant medication options in any detail, stating he believed they would be ineffective.

57. [119]

    The defendant’s breach of the ISO, the circumstances of that breach and his insight into it, together with his lack of insight into his past offending, strongly indicate that the defendant will not comply with the conditions of an ESO. Whilst the defendant maintains that he will not reoffend in the future, I note that he maintains that that an ISO or ESO breach is not a “real crime” and continues to externalise blame for his conduct. His breach of the ISO within days of release from custody with his attempt to view material depicting violent and extreme sexual behaviour, some of which apparently involved children and his externalisation of blame for this conduct, strongly indicate that further breaches would be likely should he be released to an ESO.

58. [120]

    I have set out above the defendant’s lengthy and serious criminal history. It clearly shows a pattern of continuing serious sexual offending, much of which also involved violence. This pattern of offending, as noted above as recently as January 2026, is strongly suggestive of a sexual sadism disorder.

59. [121]

    In sentencing the defendant in 1990 for serious sexual offending, Wood J made the following observations as to the defendant’s previous offending:

60. [122]

    Ten years later, in 2000, Judge Graham described the defendant’s prospects of rehabilitation as follows:

61. [123]

    However, the pattern and seriousness of the defendant’s offending was emphasised by Judge Graham:

62. [124]

    By 2006, when the defendant was being sentenced for the attack on the railway station worker which involved “extreme brutality”, Judge Marien was “unable to find, as Judge Graham did, that there are some glimmers of prospects of rehabilitation, or some glimmers of hope in that regard.” Rather,

63. [125]

    On 1 March 2007, the Court of Criminal Appeal dismissed the defendant’s appeal against the severity of the sentence imposed by Judge Marien: Wilmot v R [2007] NSWCCA 30; 169 A Crim R 280. Bell J (with whom Sully and Buddin JJ agreed) relevantly said:

64. [126]

    Judge Townsden found, in 2015, the sex offences in custody demonstrated a “continued disobedience of the law” and that “his prospects of rehabilitation remain poor”.

65. [127]

    Most recently, in 2024, Magistrate Milledge observed in the context of sentencing the defendant for the ISO breach:

66. [128]

    Later in 2024, in the context of the defendant’s unsuccessful severity appeal, Judge Pickering stated:

67. [129]

    For the purpose of assessing unacceptable risk, it is appropriate to have regard to alleged criminal conduct notwithstanding acquittal or the withdrawal of allegations (especially, as in this case, when the allegations are made in a custodial setting when there is obvious potential for retribution should matters progress to finality).

68. [130]

    Accordingly, whilst noting that they are not proven, I still attach a limited amount of weight to the fact and number of the following allegations:

69. [131]

    I agree with the plaintiff’s submission that at the very least, the above allegations, when combined with the defendant’s recent proved offending, would mean it is difficult to accept that there has been any material change in the defendant’s risk in recent years, and there would appear to be a continuation of the defendant’s pattern of behaviour, unabated.

Consideration

1. [132]

   As noted, the plaintiff made it clear at the hearing that it was primarily seeking a CDO of 12 months duration. The plaintiff was no longer also pressing for an ESO order to follow immediately after the 12 months CDO, on the sensible concession that it would simply not be possible to craft appropriate conditions 12 months in advance, even assuming an ESO was appropriate at that point.

2. [133]

   The issue for determination is thus whether the Court should make an ESO (including a line-of-sight condition) or a CDO. The defendant contended that the primary advantage of an ESO is that it can be progressively stepped down in its restrictiveness over time, whereas that could not occur with a CDO. At the same time, the defendant contended, there would be no discernible increase in risk compared to the CDO.

3. [134]

   In fairness to the defendant, the factual basis underpinning the defendant’s submission changed during the hearing. The updated RELP was only approved immediately before the hearing, and that was only notified to the Court during the hearing. Accordingly, during the hearing the defendant’s submission became progressively more difficult to sustain because the updated RELP provides a high level of flexibility, including the potential for progressively increasing overnight stays at the COSP.

4. [135]

   The seriousness of ordering the extended supervision or continuing detention of a person who is not serving a sentence cannot be gainsaid. However, the Act makes clear by s 3(1) that the primary object of the Act is to provide for the extended supervision and continuing detention of (relevantly) high risk sex offenders so as to ensure the safety and protection of the community. Rehabilitation is a secondary object. Further, s 17(2) of the Act also spells out that in determining whether to make a continuing detention order or extended supervision order, the safety of the community must be the paramount consideration of the Supreme Court.

5. [136]

   I agree with the plaintiff’s submissions that there is little variation in the substance of the expert reports prepared over almost three decades. Significantly, the experts agree that the defendant has a Borderline and Antisocial Personality Disorder, with maladaptive and psychopathic traits that are difficult to manage, modify and treat. The defendant still displays features of impulsivity, reckless disregard for the safety of others, poor insight, a lack of remorse and consistent irresponsibility. Accordingly, he has very limited ability to regulate his risk of further offending in the absence of external controls.

6. [137]

   The experts also agree that the further sexual offending would most likely involve forced penetrative sexual activity and sexual coercion against victims perceived to be vulnerable, and may involve violence, weapons, injuries to the victim, and could be perpetrated against children.

7. [138]

   Even though there was a slight divergence between the evidence of Dr Dayalan and Mr Sheehan, both agreed that a CDO would provide an appropriately graded reintegration of the defendant into the community prior to being released on an ESO, and that this would best manage the high risk posed by the defendant.

8. [139]

   Further, to the extent that the two experts differ, I agree with the plaintiff’s submission that Dr Dayalan’s evidence should be preferred over Mr Sheehan’s. Whilst there have been positive signs from the defendant when on recent external day leave that his behaviour is improving, given the level of entrenched behaviours and the extent of institutionalisation of the defendant, the defendant has only had a very short time to modify decades of dysfunctional behaviours. The evidence shows that a 12-month CDO provides a high-level ability for flexible and staged progression back into the community, with the capacity to step back and adjust to the defendant’s needs during the course of the CDO.

9. [140]

   It is true that, at first blush, there is little practical difference between an ESO with a line-of-sight condition and a CDO. However, when looked at more closely, that is not the case. As made very clear by Ms Coe, a CDO provides for additional flexibility in responding to the behaviour of the defendant, as compared to an ESO. For instance, if a problem occurs (as it did on 19 February 2026), the custodial arrangements and/or leave entitlements can be immediately modified in a proportionate and responsive manner, without the ramifications of a breach of an ESO (which may have more formal and serious consequences, or may confine him to the COSP with attendant risks to the other residents and staff). In addition, the line-of-sight supervision for someone on an ESO is constrained by resources after 6 weeks, which may mean that either the defendant would likely be more confined to the COSP (again, with attendant risks to fellow residents and staff) or there would be a real incentive for him to be transitioned away from line-of-sight supervision (with obvious risks to the community). This same constraint does not apply to a CDO. For a person in the position of the defendant, a CDO clearly provides a high level of adaptable support for the defendant and a high level of protection for the community.

10. [141]

    Although the defendant has mostly exhibited positive behaviours on his recent episodes of external day leave, there are clear signs from as recently as 19 February 2026 that he can still exhibit highly volatile and uncontrolled behaviour. He continues to exhibit lack of insight and has limited understanding of the need to implement strategies so as not to reoffend. Moreover, as noted, the period over which the recent external day leaves have occurred is an extremely short period in the context of the defendant’s decades long criminal history and incarceration, lack of insight and level of institutionalisation. When that is combined with his obvious ongoing sexual interest (exemplified by his most recent offending, his comments made to the experts as well as behaviours observed on 19 February 2026), his criminal history, and the recent allegations against him in custody, I am satisfied to a high degree of probability that the defendant poses an unacceptable risk of committing another serious offence of a sexual nature if not kept in detention under a CDO.

11. [142]

    In my opinion, the level of flexibility provided by a CDO to prepare the defendant as well as possible for eventual release would mitigate his risk to an acceptable level as well as provide the community with the best possible safety outcome. As noted, the level of flexibility can be adjusted to the defendant’s needs as required, including gradually stepping up overnight stays, but if necessary stepping back for short periods to assist the defendant and protect others.

12. [143]

    In all the circumstances and noting that the primary focus must be on the safety of the community, I am of the view that a CDO, as sought by the plaintiff, should be made.

13. [144]

    As to the length of the CDO, the plaintiff submits that a 12 months CDO is appropriate. I note that Mr Sheehan was of the view that a period of two to six months was appropriate, and that Dr Dayalan stated that if there were no “hiccups” a period shorter than 12 months may be appropriate.

14. [145]

    In my view, however, a CDO with a duration of 12 months is appropriate. The defendant’s history, his level of institutionalisation, his lack of insight and his volatility make it appropriate that he is subject to a CDO of 12 months as it will allow him to have a carefully staged transition to the community over a suitable length of time.

Orders

1. [146]

   Accordingly, I make the following orders:

   1. (1)

      Pursuant to ss 5C and 17(1)(b) of the Crimes (High Risk Offenders) Act 2006 (NSW), the defendant is subject to a continuing detention order for a period of 1 year commencing 20 March 2026 and expiring on 19 March 2027.

   2. (2)

      Pursuant to s 20(1) of the Crimes (High Risk Offenders) Act 2006 (NSW), a warrant is to be issued for the committal of the defendant to a Correctional Centre for the purposes of order (1).