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Court of Criminal Appeal 23 June 2025

O’Dwyer v R

[2025] NSWCCA 95

Fraud & dishonesty
CRIME APPEALS APPEAL AGAINST SENTENCE WHETHER BREACH OF DE SIMONI PRINCIPLE APPEALS APPEAL AGAINST SENTENCE

Citation: O'Dwyer v R [2025] NSWCCA 95
Court: NSW Court of Criminal Appeal
Date: 23 June 2025
Judges: Mitchelmore JA (with Rothman J and Yehia J agreeing)

Background

The applicant was the managing director and founder of the Ralan Group, a property development enterprise. He pleaded guilty in the District Court to six counts of dishonestly obtaining a financial advantage by deception, contrary to s 192E(1)(b) of the Crimes Act 1900 (NSW). The offences spanned April 2015 to June 2018 and involved loan facilities obtained from St George Bank and Wingate Pty Ltd on behalf of three Ralan Group development companies, of which he was the sole director.

The deception centred on misrepresentations to the lenders about off-the-plan pre-sale deposits. The applicant falsely represented that those deposits were held in trust accounts and were not subject to any side agreements. He also provided misleading trust account ledgers, schedules of pre-sale deposits, and other documentation attesting that pre-conditions of the loan facilities had been satisfied, knowing the documents were misleading.

The District Court imposed an aggregate prison term of four years, commencing 2 February 2024, with a non-parole period of two years and four months. The applicant sought leave to appeal against that sentence on three grounds.

  • Whether the sentencing judge breached the De Simoni principle by assessing objective seriousness by reference to facts that would constitute the more serious offence under s 193B of the Crimes Act 1900 (NSW) (Ground 1)
  • Whether the aggregate sentence was manifestly excessive (Ground 2)
  • Whether the sentencing judge erred in assessing objective seriousness by reference to the quantum and period of loan drawdowns, and failed to account for the applicant's alleged "risk management" conduct and the absence of loss to the lenders (Ground 3)

Decision

Ground 1 (De Simoni breach): The Court rejected the contention that the sentencing judge sentenced the applicant for criminality referable to the more serious s 193B offence. Reading the sentencing remarks as a whole, the judge's references to the period and quantum of drawdowns were not deployed to aggravate objective seriousness. Rather, those references reflected matters the judge regarded as beneficial to the applicant. The Court held that the applicant's argument rested on a misreading of the sentencing remarks.

Ground 3 (objective seriousness and risk management): The Court found that the applicant's submissions did not fairly reflect the totality of the sentencing judge's reasoning. A proper reading of the sentencing remarks showed that the absence of loss was considered in the context of objective seriousness. The applicant's "risk management" argument, premised on maintaining an undrawdown balance in the facilities at least equal to the security amount, was rejected as misconceived. Leaving funds undrawn within the lenders' own facilities did not independently secure the debt; the lenders had been led to believe that security existed separately and independently, which was precisely the point of the deception.

Ground 2 (manifest excess): This ground was advanced largely on the premise that Ground 1 would succeed. Having dismissed Ground 1, the Court also dismissed Ground 2 on that basis. The applicant's additional contention, that the judge failed to revisit objective seriousness after finding absence of loss to be a mitigating factor, relied on the same disjunctive reading of the sentencing remarks rejected under Ground 3.

Orders Made

  • Leave to appeal against sentence is granted.
  • The appeal is dismissed.

Key Takeaways

  • The De Simoni principle prohibits a sentencing court from taking into account, as an aggravating factor, conduct that would constitute a more serious offence than the one charged. The Court of Criminal Appeal confirmed that applying that principle requires a careful and holistic reading of the sentencing judge's reasons, not a selective or disjunctive interpretation.
  • Where sentencing remarks refer to facts associated with a more serious offence, a breach of De Simoni is not established merely by pointing to those references; the applicant must show that the judge actually used those facts to increase, rather than reduce or contextualise, the sentence.
  • Assessing whether a mitigating factor was properly considered requires reading the sentencing remarks as a whole. An absence of express revisitation of objective seriousness after a mitigating finding does not, of itself, establish that the mitigating factor was overlooked.
  • The "risk management" argument advanced by the applicant, based on maintaining an undrawn balance in the loan facilities equal to the required security amount, was rejected. Leaving funds available within the lenders' own facilities does not constitute independent security where the entire premise of the lending was that security existed separately.
  • In dismissing all three grounds, the Court reinforced that a manifestly excessive sentence ground that depends substantially on the success of other grounds will ordinarily fail alongside those grounds.

Legislation and Cases Referenced

Legislation:
- Crimes Act 1900 (NSW), ss 192E, 193B
- Crimes (Sentencing Procedure) Act 1999 (NSW), s 21A

Cases:
- The Queen v De Simoni (1981) 147 CLR 383; [1981] HCA 31
- Turkmani v The Queen [2014] NSWCCA 186; 244 A Crim R 402
- R v Todorovic [2008] NSWCCA 49
- R v Woodman [2001] NSWCCA 310