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Court of Criminal Appeal 20 March 2026

Hildebrand v R (No. 2)

[2026] NSWCCA 23

Sexual offencesPublic order & justice offences

Citation: Hildebrand v R (No. 2) [2026] NSWCCA 23
Court: NSW Court of Criminal Appeal
Date: 20 March 2026
Judge(s): Kirk JA, Sweeney J, Coleman J (Coleman J writing the lead judgment)

Background

The applicant was convicted after pleading guilty to 26 charges (with 18 additional matters taken into account) arising from a prolonged course of offending between 2007 and 2016. The offending involved attempting to blackmail young women known to the applicant into providing explicit photographs or sexual favours, under threat of disseminating intimate images. The applicant created false online identities and, in some cases, victims confided in him — not knowing he was the person behind the threatening demands. The applicant was aged between 19 and 28 during the offending and was a serving NSW police officer from December 2011.

The applicant was originally sentenced in September 2019 to an effective term of 20 years' imprisonment with a non-parole period of 15 years. He appealed to the Court of Criminal Appeal, which in Hildebrand v R [2021] NSWCCA 9 upheld one ground — an error in using the NSW Form 1 procedure for certain Commonwealth charges — but dismissed all other grounds. The matter was remitted for resentencing before the same District Court judge. Following resentencing on 10 February 2022, the applicant received the same effective sentence: 20 years' imprisonment with a 15-year non-parole period.

The applicant, who was self-represented, filed a Notice of Intention to Appeal promptly but did not file the Notice of Appeal until October 2025 — well out of time. He explained that Legal Aid had denied him funding, pro bono referral services had been unsuccessful, and he faced significant practical difficulties conducting legal research while incarcerated.

  • Extension of time: Whether the applicant should be granted an extension of time to file the Notice of Appeal, given the delay of approximately three and a half years.
  • Apprehension of bias: Whether comments made by the sentencing judge — particularly indicating that, absent further submissions, her Honour was likely to reach the same findings as in the original sentencing — gave rise to an apprehension of bias in the resentencing hearing.
  • Procedural unfairness: Whether the sentencing judge acted with procedural unfairness by rejecting a diagnosis of "unspecified paraphilic disorder" that had been tendered on behalf of the applicant but was not the subject of challenge by the Crown or cross-examination.
  • Error of fact regarding COVID-19: Whether the sentencing judge erred in her remarks concerning the impact of COVID-19 restrictions on the applicant's conditions in custody.
  • New evidence: Whether two new expert reports (prepared by Dr Pusey and Dr Furst for use in separate District Court sentencing proceedings) should be admitted as fresh or new evidence on appeal.

Decision

Extension of time was granted. Coleman J (with Kirk JA and Sweeney J agreeing) noted the applicant's difficulties in securing legal representation and the practical challenges he faced as a self-represented prisoner. In the interests of finality, the Court allowed the late filing and granted leave to appeal.

On the apprehension of bias ground, the Court found no basis for apprehended bias. The sentencing judge had made clear at the outset of the resentencing hearing that she was likely to reach the same findings absent new material or submissions, but critically, her Honour had also invited the parties to put on additional evidence and make further submissions. The Court held that this approach was not one that would cause a fair-minded lay observer to apprehend that the judge might not bring an impartial mind to the task. Rather, it was an appropriately transparent indication of the judge's tentative reasoning, given the narrow nature of the resentencing exercise.

Regarding procedural unfairness, the Court found that the applicant's legal representatives at the resentencing hearing were well aware — from the first sentencing judgment — that the judge had reservations about the diagnosis of unspecified paraphilic disorder. Her Honour had made her views clear in the original reasons. Despite this, the applicant's representatives made no additional submissions on the diagnosis at the resentencing hearing. In those circumstances, the Court held there was no procedural unfairness in the judge reaching the same conclusion she had previously reached on the same material.

On the COVID-19 point, the Court found that a reference in the remarks on sentence to COVID-19 was "plainly a slip." No submissions had been made by the applicant's representatives regarding COVID-19 making custody more onerous, and the applicant had not established that consideration of this factor would have reduced the sentence to a degree that would render the outcome a serious injustice or miscarriage of justice.

Finally, the new evidence ground was rejected. The two expert reports did not cast new light or offer new conclusions on the circumstances of the offending. The Court could not conclude that their absence resulted in a miscarriage of justice or that they would have had a real bearing on the sentencing discretion. The Court also addressed a related concern: the sentencing judge's factual findings regarding the inapplicability of the paraphilic disorder diagnosis were findings of fact that would not bind a different District Court judge in any subsequent sentencing proceedings.

Orders Made

  • Extension of time to file the Notice of Appeal: granted
  • Leave to appeal against sentence: granted
  • Appeal: dismissed

Key Takeaways

  • Transparency is not bias: The Court of Criminal Appeal held that a resentencing judge who indicated a tentative view, while inviting further submissions and evidence, did not give rise to an apprehension of bias. A fair-minded lay observer would distinguish between a closed mind and an informed preliminary assessment, particularly where the resentencing exercise was narrow in scope.

  • Where a sentencing judge's concerns are apparent from earlier reasons, the defence bears a practical obligation to address those concerns with further evidence or submissions at resentencing. The failure to do so did not later ground a procedural unfairness argument, as the Court found the applicant had been given a meaningful opportunity to respond.

  • Expert reports prepared for other proceedings will not be admitted on appeal unless they cast genuinely new light on the sentencing exercise and their absence can be shown to have resulted in a miscarriage of justice. In refusing to admit the new evidence, the Court confirmed the high threshold for fresh material on a sentence appeal.

  • No issue estoppel arises from sentencing findings: A sentencing judge's factual findings, even on contested psychiatric diagnoses, do not bind a different judge in separate proceedings. The Court of Criminal Appeal confirmed that this principle applied regardless of how thoroughly the issue had been explored at sentence.

  • In granting the extension of time, the Court acknowledged that self-represented prisoners may face genuine and sustained difficulty in obtaining legal representation, as well as practical barriers to preparing an appeal from custody. These circumstances warranted significant latitude in the interests of finality.

Legislation and Cases Referenced

Legislation:
- Crimes Act 1900 (NSW)
- Crimes Act 1914 (Cth), s 16BA
- Criminal Appeal Act 1912 (NSW), ss 5(1)(c), 6(3)
- Crimes (Sentencing Procedure) Act 1999 (NSW), s 33
- Supreme Court (Criminal Appeal) Rules 2021 (NSW), r 3.5(5)

Key Cases:
- Hildebrand v R [2021] NSWCCA 9 (the first appeal)
- Kentwell v The Queen (2014) 252 CLR 601; [2014] HCA 37
- Baladjam v R [2018] NSWCCA 304; (2018) 341 FLR 162
- Ebner v Official Trustee in Bankruptcy (2000) 205 CLR 337; [2000] HCA 63
- Concrete Pty Ltd v Parramatta Design & Developments Pty Ltd (2006) 229 CLR 577; [2006] HCA 55
- Michael Wilson & Partners Ltd v Nicholls (2011) 244 CLR 427; [2011] HCA 48
- Betts v The Queen (2016) 258 CLR 420; [2016] HCA 25
- R v Birks (1990) 19 NSWLR 677
- Lee v Huo [2026] NSWCA 15
- Lawavou v R [2025] NSWCCA 35