SLD v R

1. [1]

   STERN JA: I have had the considerable advantage of reading the reasons of Boulten J in draft. Having carried out my own independent assessment of the trial record I agree with his Honour’s analysis and with his conclusion that the applicant’s conviction was not unreasonable. I agree with the orders proposed by Boulten J.

2. [2]

   HUGGETT J: I have had the advantage of reading the draft judgment of Boulten J. Having made my own independent assessment of the whole of the evidence, taking in to account the way the case was conducted at trial and the submissions made on the appeal, for the reasons set out by his Honour, I agree with the orders proposed.

3. [3]

   BOULTEN J: In 2024, the applicant was tried in the District Court on an indictment that contained three counts against s 12 of the Crimes (High Risk Offenders) Act 2006 (“HRO Act”) alleging that he failed to comply with a requirement of his extended supervision order (“ESO”). He stood trial before Fitzsimmons SC DCJ (“the trial judge”) who presided without a jury, and he was acquitted of counts 1 and 3 but convicted of count 2. He was sentenced to imprisonment for 1 year and 6 months, with a non-parole period of 1 year and 1 month, which commenced from 24 October 2023 and expired on 23 April 2025.

4. [4]

   By notice of appeal filed on 1 December 2025, the applicant seeks leave pursuant to s 5(1)(b) of the Criminal Appeal Act 1912 (NSW) to appeal against his conviction on the sole ground that it was unreasonable. There is no appeal about the sentence that was imposed.

5. [5]

   For the reasons that follow, I consider that leave should be granted but the appeal be dismissed.

Issue raised by the appeal

1. [6]

   In short, the issue raised by the appeal is as follows: did the applicant associate with a child in breach of condition 30 of his ESO?

2. [7]

   It follows, what does it mean to associate? It is necessary to construe the meaning of this word by reference to its definition within the ESO. It is only then that I can, consistently with the principles enunciated below, determine if it was open to the trial judge to be satisfied beyond reasonable doubt that the applicant was guilty.

The legal principles

1. [8]

   For appeals advanced on the basis of unreasonable verdicts, the necessary starting point is s 6(1) of the Criminal Appeal Act:

2. [9]

   The principles are now well established and apply to unreasonable verdict appeals generally, even in appeals such as this, where the issue to be resolved is ultimately quite a narrow one. [1]

3. [10]

   In M, the plurality of the High Court (Mason CJ, Deane, Dawson and Toohey JJ) observed at 493:

4. [11]

   The plurality in M also provided the following guidance, at 494:

5. [12]

   The High Court in Dansie, when referring to M, observed the following at [8] (Gageler, Keane, Gordon, Steward and Gleeson JJ):

6. [13]

   The principles apply equally to judge alone trials. [2] In Slattery v R [2023] NSWCCA 117 (“Slattery”), Bell CJ (with whom Ward P and Wilson J agreed) consolidated the principles that followed from Dansie and Filippou at [113] – which helps explain how appellate courts, as applicable here, are to approach unreasonable verdict appeals where an accused person is convicted after a judge alone trial:

Key evidence

1. [14]

   The salient evidence, as summarised below, is not in dispute between the parties.

2. [15]

   The applicant is subject to an ESO. Campbell J imposed the ESO for a period of 5 years, commencing on 15 August 2023 and expiring on 18 August 2028, in State of New South Wales v SLD (Final) [2023] NSWSC 978.

3. [16]

   Condition 30 of that ESO reads as follows:

4. [17]

   The term “associate” is defined by the ESO, as follows:

5. [18]

   On 24 October 2023, the applicant visited Bulli Beach where he approached several women, three of whom each had a small child or children in their care. The applicant was in the habit of approaching women to ask them out on dates. His approaches were not nuanced and were probably unsuccessful. Jason Saad, who often supervised him as part of his role as a Departmental Supervising Officer (“DSO”), provided the following evidence: [3]

6. [19]

   So, the applicant’s behaviour on 24 October 2023 was not, for him, unusual. Nor was it an offence for him to ask women out on dates. The conditions of his ESO do not prohibit that. But it is an offence for him to associate with someone that he knows, or reasonably should know, is under 18 years of age (unless an exception within condition 30 of the ESO applies).

7. [20]

   The crucial evidence relates to the applicant’s approach to, and interaction with, a woman whom I will refer to as “Ms A” while at Bulli Beach on 24 October 2023. The evidence of this, as outlined below, underpinned the count on which he was convicted.

8. [21]

   Ms A was with her 10-month-old son at an outdoor shower adjacent to the Bulli Beach Surf Club when the applicant approached her. Ms A’s evidence about her interaction with, and proximity to, the applicant is encapsulated by the following questioning during her examination in chief: [4]

9. [22]

   Also, centrally, Ms A gave evidence that: [5]

10. [23]

    The applicant did not seek to challenge Ms A’s account.

11. [24]

    Quite coincidentally, an off-duty Senior Community Corrections Officer, Lucas Clark, was also at Bulli Beach that day. Mr Clark noticed that the applicant was wearing an electronic monitoring anklet. He continued to observe the applicant as he approached a number of women with small children. Mr Clark described the applicant’s interaction with Ms A as follows: [6]

12. [25]

    Mr Clark also said:

13. [26]

    It follows that Mr Clark’s and Ms A’s accounts were not entirely harmonious. Mr Clark mistook relevant details, such as the gender and age of Ms A’s child. It was well open to the trial judge to make the following finding: [7]

14. [27]

    This constituted the full body of salient evidence underpinning count 2.

15. [28]

    The Crown also led evidence that the applicant approached two other women that day who, like Ms A, had young children with them. I am bound by the acquittals in respect of the counts which related to those interactions, and I do not consider it necessary to outline the evidence that underpinned those events.

16. [29]

    The applicant also approached a fourth woman at the nearby Bulli Beach Café. This did not involve any alleged criminality. This particular woman gave evidence that she worked at the Café and the applicant approached her and asked whether she was old enough to date. She said she was 25-years-old. He replied, “You’re 25. You look incredibly young”. The applicant then told her that he had been in gaol since he was 13 and that he was still a virgin. Nothing else relevant happened with this young woman.

The trial judge’s findings on “associate”

1. [30]

   At trial, the crucial issue was whether the applicant associated with someone he knew, or reasonably should have known, was under 18 years of age in breach of condition 30 of his ESO. In acquitting the applicant of two counts and convicting him of one count, his Honour construed the meaning of “associate” in the following manner, per [109]-[112] of his verdict:

Elements of the offence

1. [31]

   Before turning to the parties’ submissions on the appeal, it is desirable to identify the elements of the offence charged.

2. [32]

   The applicant was convicted of failing to comply with his ESO per s 12 of the HRO Act. Section 12 provides:

3. [33]

   Specifically, the applicant breached condition 30 of the ESO – as outlined above already.

4. [34]

   The elements of the offence, as per the trial judge’s reasons, were as follows: [8]

Submissions

1. [35]

   In summary, the applicant embraces the trial judge’s interpretation of “associate” but contends that the evidence does not allow for a conclusion that he breached condition 30 of the ESO.

2. [36]

   Central to that position is the contention that “to associate” with a person under the age of 18, requires sufficient contact that meets a qualitative (and quantitative) threshold, consistent with the trial judge’s findings as I referred to above. That is, the conduct must rise to the level of forming a direct interpersonal connection (a connection of substance) with the child.

3. [37]

   In embracing his Honour’s construction of the term “associate”, the applicant submitted that the relevantly charged conduct did not amount to a breach of condition 30. He contended there was no connection, let alone connection of substance, with the child. He pointed to the particular features of his interaction with Ms A and noted there was no engagement with, attempt to communicate with, or attention directed towards the child.

4. [38]

   At the appeal hearing, Mr Broadbent SC, who appeared on behalf of the applicant with Mr Bhutani, acknowledged that the threshold question for this Court is whether the applicant was “in company with” Ms A’s child – which flows from the definition of “associate” in the ESO. He conceded that if the Court is satisfied that the applicant was “in company with” Ms A’s child, and the mental element is satisfied, then the applicant’s appeal fails.

5. [39]

   In any case, Mr Broadbent SC submitted that the applicant was not “in company with” Ms A’s child. He argued there was no evidence to support that position. In doing so, he drew a distinction between being “in company with” and “in the company of”, arguing that the former has work to do and requires a closer form of connection than the latter. But, in essence, the crux of the applicant’s submission on this point was that the evidence does not establish any meeting of the minds between the applicant and Ms A’s child. [9]

6. [40]

   Separately, the applicant also focussed on the mental element of the offence. Submissions were advanced against the trial judge’s findings as to the mens rea requirement of the offence, where his Honour concluded (at [133]): [10]

7. [41]

   In this respect, the applicant made two points: first, that the trial judge elided the concepts of “intention” and “voluntariness” and it does not necessarily follow that, because the applicant freely and voluntarily engaged in a conversation with Ms A, he intended to associate with her child; and secondly, his Honour’s findings were directed at the applicant’s engagement with Ms A, not her child. In this regard, it was submitted that without more, the applicant simply knowing that the child was present does not amount to a breach of condition 30.

8. [42]

   The respondent presented a competing view, arguing that his Honour’s construction of “associate” was unduly narrow and it is instead capable of encompassing intentional physical proximity to a child.

9. [43]

   More broadly, the Crown contended that the task of this Court in determining the unreasonable verdict appeal, is, like the trial judge did, to consider the meaning of the word “associate” in condition 30 of the ESO. The respondent argued: [11]

10. [44]

    The following paragraphs are particularly illustrative as to the core features of the Crown’s argument:

11. [45]

    As the applicant did, the respondent developed arguments in relation to the mental element of the offence. But, unlike the applicant, the Crown was not so concerned about alleged deficiencies in the trial judge’s reasons. Instead, emphasis was simply placed upon the role of the appellate court when determining appeals under s 6(1) of the Criminal Appeal Act – and from there, it will be seen it was open to the trial judge to find beyond reasonable doubt that the applicant intentionally associated with the child.

A preliminary issue: did the Crown’s case unfairly change?

1. [46]

   Before turning to further consideration of this appeal, it is important to note that the applicant made an ancillary complaint of procedural fairness. In short, he contended there was a fundamental and unfair change in the way that the Crown led its case between the trial and the appeal.

2. [47]

   In doing so, Mr Broadbent SC directed the Court’s attention to various parts of the trial record. First, he referred to [89] of the trial judge’s verdict, which is provided as follows: [12]

3. [48]

   He then referred to particular remarks made during the Crown’s opening address. Specifically, he referred to the following submission advanced by the Crown: [13]

4. [49]

   Mr Broadbent SC also turned to the Crown’s closing submissions at trial. In this context, the Crown submitted: [14]

5. [50]

   So, it was contended that the respondent ran its case by arguing that the applicant used the mothers he approached as a proxy to deliberately contact their children. On the appeal, Mr Broadbent SC said: [15]

6. [51]

   According to Mr Broadbent SC, the Crown advanced its case on a more easily proved basis in this appeal. Specifically, it was argued that the Crown moved beyond its proxy argument and now contended that to be “in company with” “denotes physical presence with another person in a way that is more than mere or fortuitous proximity in a public place – for example, standing together at a bus stop or side-by-side in a queue”.

7. [52]

   In reply, the respondent submitted there was no such shift in the Crown case. It was noted that the Crown’s construction of the term at trial was broad and it is the same broad construction that is advanced on the appeal. Specifically, the Crown at trial not only submitted that the applicant approached women as a proxy to their children, but also that the applicant was liable for conviction because he was “in company with” the children in circumstances that were more than just fortuitously proximate.

8. [53]

   I regard the respondent’s position at trial to have been an attempt to advance two ways in which the applicant could be convicted; first, if the trial judge was satisfied beyond reasonable doubt that the applicant was using the mother of the child as a proxy or if he used stealthy measures to gain access to the child; and secondly, without needing to be convinced of such a motive, the applicant was, in any event, in the child’s company in circumstances that were more than just fortuitously proximate. Both positions were, at different times, articulated in the trial court.

9. [54]

   For example, the Crown submitted in its opening address: [16]

10. [55]

    Additionally: [17]

11. [56]

    It can hardly be said the applicant was not alive to the scope of the Crown’s argument. Indeed, the applicant’s trial counsel made the following submission in his closing address: [18]

12. [57]

    Quite clearly, the Crown did not advance its case solely upon the basis of its “proxy” argument. There was no unfair shifting of the prosecution’s case. The applicant’s ancillary argument should not be accepted and, accordingly, there is no such need to consider the possible forms of relief.

Consideration

1. [58]

   In resolving this appeal, the Court must consider the true meaning of the word “associate” in condition 30 of the ESO. As foreshadowed previously, the Court will be able to then, and only then, ask itself the ultimate dispositive question in accordance with the relevant principles.

2. [59]

   Generally, the true meaning of court orders can be ascertained according to the ordinary rules of construction. In Australian Consolidated Press Ltd v Morgan (1965) 112 CLR 483; [1965] HCA 21 (“Morgan”), Windeyer J, at 503, commented about the related task of construing the terms of an undertaking:

3. [60]

   The Court of Appeal in Henderson v Harvey [2026] NSWCA 56 (at [39]-[40]) recently cited Morgan, amongst other cases, when outlining “the relevant legal principles which guide the task of construction” of a consent order which provides analogous guidance to the current exercise. Griffiths AJA, with whom McHugh JA and Harrison AJA agreed, held at [40(d)]:

4. [61]

   As Kunc J observed in Bathurst Real Estate Ltd v Fairbrother [2022] NSWSC 351 (at [57]):

5. [62]

   Turning to this appeal, the starting point for statutory construction is, as the High Court said, “the text of the provision considered in light of its context and purpose”. [19]

6. [63]

   Condition 30 falls under “Part F: Non-association” of the order. It prohibits the applicant from associating with anyone that he knows, or reasonably should know, is under 18 years of age. Instructively, condition 30 contains an exception. The prohibition on association does not apply to “incidental contact in a public place in the course of the duties of the minor”.

7. [64]

   This suggests that any association, including incidental contact, with a person under 18 years of age, other than that contact encompassed by the exception, exposes the applicant to a breach of the condition and, therefore, liable for criminal punishment.

8. [65]

   But all of this begs the following question: what does it actually mean to associate with someone? As noted already, “associate” is a defined term within the order, and it includes “being in company with”. Though not defined by the order, “being in company with” is at the heart of what the Crown says the applicant did to breach condition 30 of the ESO.

9. [66]

   The parties advanced competing submissions at trial as to how to construct “associate” and, in doing so, they relied upon separate dictionary definitions. This, in my view, lacks any real utility in this case. While of course the dictionary can at times provide some degree of assistance, Leeming J observed in TAL Life Ltd v Shuetrim (2016) 91 NSWLR 439; [2016] NSWCA 68 at [80] (Beazley P and Emmett AJA agreeing):

10. [67]

    Here, the context in which “associate” is employed is particularly important. When a person is subject to an ESO, they require absolute clarity about what they can and cannot do. There should be little, if any, room for ambiguity. This is because the consequences that flow from a breach are very serious; proved breaches carry severe criminal penalties, including imprisonment like in this case.

11. [68]

    So, while the dictionary may assist to some extent, it is possible that, once regard is given to its context and purpose, “associate” will carry a different meaning than it does in the dictionary. The relevant context should be considered irrespective of whether any ambiguity is thought to arise. [20]

12. [69]

    It is therefore necessary, in ascertaining the meaning of “associate”, to consider the context of the ESO and its enabling Act, namely, the HRO Act. Relevantly, s 3 of the HRO Act identifies its two main objects, which are as follows:

13. [70]

    The HRO Act operates to ensure that serious offenders are the subject of potentially significant incursions on their liberty. It enables the Supreme Court to make orders for the supervision of particular offenders even after the conclusion of a custodial sentence. As s 3(1) makes plain, this is primarily to ensure the safety and protection of the community. However, ESO’s can only be made after the State of New South Wales has satisfied the Supreme Court that various jurisdictional pre-conditions are met. Specifically, s 5B provides for when such an order may be made, as follows:

14. [71]

    If the Court is satisfied as to s 5B, then it may make an ESO pursuant to the discretion conferred to it by s 9(1). But, in exercising that discretion, s 9(2) mandates the safety of the community as the paramount consideration for the Court.

15. [72]

    With this kept in mind, it can be comfortably concluded that the principal objective of the HRO Act, and by extension an ESO, is to ensure community safety.

16. [73]

    While it is not necessary to consider the circumstances in which the relevant ESO was made, it is nevertheless of some assistance. As noted previously, Campbell J imposed the ESO in 2023. In the judgment (State of New South Wales v SLD (Final) [2023] NSWSC 978), his Honour observed the very serious nature of the index offending that enlivened the operation of the HRO Act in the first place. Specifically (at [7]):

17. [74]

    The extremely serious nature of the index offending simply reinforces that the ESO, and condition 30 in particular, were put in place to firmly mitigate against risks that the applicant posed to children in the community. The relevant condition was aimed at preventing the applicant from harming children by limiting his exposure to children – including through simply being in their company.

18. [75]

    In these circumstances, it was well open to infer on the evidence that the applicant approached Ms A knowing that she was caring for and dealing with her child and then he engaged Ms A in a conversation about her child.

19. [76]

    It is not necessary, in my opinion, to ascertain the meaning of “associate” by resorting to different hypothetical situations that simply do not arise on the evidence. There is sufficient evidence here to allow for a conclusion that the applicant deliberately and intentionally put himself in the company of both Ms A and her child.

20. [77]

    The applicant deliberately and intentionally put himself in the company of a child (within earshot and close enough for the applicant to see that the child had red spots on his body) in circumstances which were prohibited by condition 30. This conclusion finds support in the purpose of condition 30, which is to guard against the risk of serious offending against children. Likewise, the HRO Act itself is directed at protecting against this very same risk.

21. [78]

    This leads to a question of what is meant by an intentional breach. The applicant argued that the relevant mens rea requires an intention to “associate” with a child and that the applicant’s intentional engagement with Ms A in her child’s presence was insufficient to establish an intention to “associate” with the child.

22. [79]

    The respondent argued that the trial judge was correct in concluding that the relevant intention was the applicant’s intention to engage in the conduct which was found to have constituted “associating” with the child. It was argued that it was not necessary to prove that the applicant subjectively characterised the conduct as being for the purpose of associating with the child.

23. [80]

    The respondent’s approach is, in my view, correct. Even if the applicant may be accepted as having mistakenly characterised the legal effect of his intentional acts, that does not mean that he did not intend to be in the child’s company – and, therefore, to associate with the child. His Honour was not in error.

24. [81]

    I have read the entire trial record, and I am satisfied beyond reasonable doubt that the applicant was intentionally in the company of a child whom he knew was under 18 years of age and that his conduct was not with the written permission of a DSO and in accordance with any requirements reasonably determined by a DSO. He was, therefore, in breach of condition 30 of the ESO. The conviction below was properly arrived at. It was not unreasonable or contrary to the evidence.

25. [82]

    I propose to make the following orders:

    1. (1)

       Leave to appeal is granted.

    2. (2)

       The appeal is dismissed.