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Australian Poker Hall of Famer Gary Benson has lost a legal battle to recover almost A$50,000 in gambling debts from fellow poker player Michael O’Grady, despite having previously won a court judgment on the same matter.
The Downing Centre Local Court ruling did not dispute that O’Grady placed the bets or owed the money. Instead, Judge Scott Nash determined that Benson had effectively been operating as an unlicensed bookmaker, which made the debt unenforceable under the New South Wales Unlawful Gambling Act 1998.
Court evidence showed a detailed ledger kept by Benson recording 211 separate betting transactions between May 2022 and February 2023. O’Grady would propose sports bets with specific amounts and odds, which Benson would then accept or decline, including one exchange involving a A$5,000 wager on a rugby league match.
Rather than settling each bet individually, the two carried an ongoing balance, with Benson also extending credit to O’Grady. On one occasion, records showed A$70,000 in wagers placed in a single day, including two bets worth A$20,000 accepted within minutes of each other.
Benson had initially won a judgment against O’Grady in 2023 for over A$45,000. The pair later struck a new agreement for repayment through O’Grady’s future tournament winnings, with Benson giving up his original enforcement rights. When that deal fell through, Benson returned to court, but this time the legality of the underlying betting arrangement became central to the case, resulting in his claim being dismissed and an order to pay legal costs.
Benson made history in 1996 as Australia’s first WSOP bracelet winner and has since earned more than $2.8 million in tournament winnings.
