Poker legend's courtroom gamble ends in defeat after he let a mate rack up massive debts - and then lost the lot in a judge's landmark ruling

- See more Daily Mail on Google - save us as a Preferred Source One of Australia's most successful professional poker players has gambled on the legal system to recover almost $50,000 in debts allegedly owed to him by a fellow punter and lost. uncertain

Gary Benson was an inaugural member of the Australian Poker Hall of Fame with career earnings of $2,826,031, putting him 20th on the local all-time money list. The 69-year-old has his own Wikipedia entry and holds a World Series of Poker bracelet, the most coveted non-monetary prize a player can win on the international circuit. He has also practised as a chartered accountant since 1985 and specialised for three decades in advising Australian poker players on their tax obligations in the US. Benson's 52-year-old sometime rival Michael O'Grady might be less well known on the poker tour but still ranks 56th on the Australian money list, with career earnings of $1,657,979. As well as playing cards, O'Grady also likes to bet big on sports - AFL, NRL, NFL, UFC, motor racing, tennis, soccer and golf - and found in Benson someone prepared to accept his private bets. O'Grady and Benson, both from Sydney, had known each other for several years when they became involved in an ongoing gambling arrangement which landed them both in court. uncertain

Benson would ultimately be found to have acted as an unlicensed bookmaker, and as such, O'Grady could not be forced to repay any debt he owed him because such gambling was prohibited. uncertain

Gary Benson, one of Australia's most successful professional poker players, has gambled on the legal system to recover almost $50,000 in debts owed to him by a fellow punter and spectacularly lost. asserted

Benson is pictured Gary Benson and Michael O'Grady (above), who also plays on the international poker circuit, had known each other for several years when they became involved in an ongoing gambling arrangement which landed them both in court Downing Centre Local Court judge Scott Nash described the nature of the pair's arrangement in a landmark decision handed down this week which set Benson back $48,711.84, plus legal costs. ' asserted

Initially, that relationship appears to have been relatively informal,' Judge Nash found. asserted

'However, over time it developed into a sustained course of betting activity involving repeated wagering transactions conducted over an extended period. asserted

While Judge Nash said 'the precise detail of every wager is unnecessary to recount', a betting ledger showed 211 transactions between May 2022 and February 2023. uncertain

'This was not a case involving one or two isolated bets,' Judge Nash found. asserted

'Nor was it a case involving occasional social wagering. asserted

The evidence further establishes that odds were quoted, discussed and agreed. asserted

Mr Benson was not merely participating in bets proposed by others. ' asserted

He occupied the position of receiving wagering propositions and agreeing the terms upon which betting would occur.' asserted

O'Grady placed his bets by text messages, such as the following exchange in which he wanted to put $5,000 on the Cronulla-Sutherland Sharks to beat an NRL opponent by at least 12 points for a return of $9,300. asserted

Benson (above) was an inaugural member of the Australian Poker Hall of Fame with career earnings of $2,826,031, putting him 20th on the local all-time money list O'Grady: "Gaz can I have 5K sharks -11.5 @1.86" Benson: asserted

'Outcomes of the wagers were subsequently recorded and liabilities calculated according to those outcomes,' Judge Nash said. uncertain

'A feature of the parties' dealings was that liabilities were not invariably settled immediately following the completion of a particular event or wager. asserted

Instead, wins and losses were often carried forward and incorporated into an ongoing balance between the parties.' asserted

From time to time, Benson extended credit to O'Grady and 'the relationship developed characteristics that were financial as well as recreational'. asserted

On one occasion, Benson accepted two wagers totalling $20,000 within about two minutes. asserted

The ledger recorded Benson receiving $70,000 in wagers from O'Grady on August 12, 2022. asserted

O'Grady placed bets with Benson by text messages, such as the exchange in which he wanted to put $5,000 on the Cronulla-Sutherland Sharks to beat an NRL opponent by at least 12 points ' asserted

Expressed another way, the relationship between Mr Benson and Mr O'Grady was not merely an agreement that the parties would occasionally select opposing teams and bet with each other on a social or casual basis,' Judge Nash said. asserted

The arrangement contemplated that Mr O'Grady would communicate the bet he wanted, Mr Benson would decide whether to take it, the odds and amount would be agreed and fixed and the resulting liability would be settled on credit later. asserted

' As O'Grady's betting continued, the amounts said by Benson to be owed to him 'increased substantially' and were 'not insignificant', according to Judge Nash. uncertain

'Discussions concerning repayment occurred and, for a time, the parties attempted to manage the position without recourse to the courts,' Judge Nash said. asserted

Benson commenced legal proceedings against O'Grady in May 2023, seeking the recovery of money he claimed he was owed - $42,488.58, plus interest and costs. uncertain

Judgement was made in favour of Benson in July that year and O'Grady was ordered to pay him $45,035.94 but during April and May 2024 the parties began negotiating a 'compromise agreement'. uncertain

Under that agreement, O'Grady would pay Benson $48,711.84, representing the judgment debt and accrued interest, out of prize money from future poker tournaments. asserted

As part of the undertaking, Benson surrendered enforcement rights of the original judgment and a third man acted as his guarantor. asserted

A spreadsheet (above) Benson maintained of O'Grady's sports betting between May 2022 and February 2023 listed events, wagers, potential wins, results and an ongoing balance In the end, the compromise agreement was not followed and Benson took both O'Grady and the third man back to the local court to have it enforced. uncertain

The case did not turn on whether the debt or compromise agreement existed, but rather whether Benson had been acting as an unlicensed bookmaker. asserted

'Gambling has become an enduring feature of professional sport and racing,' Judge Nash said in his judgment. asserted

'Viewers of sporting and racing broadcasts will be familiar with the warning, "You win some, you lose more", popularised by the title of the 2023 Australian parliamentary inquiry into online gambling and its impacts. asserted

Another familiar warning is, "Chances are you’re about to lose". asserted

In a sense, both expressions have some relevance to these proceedings. asserted

O'Grady and the third man were represented by Tony Taouk, of Magna Carta Lawyers, instructing barrister Jethro Horowitz. asserted

Benson contended his dealings with O'Grady 'amounted to little more than private betting between acquaintances', and the compromise agreement was a binding contract. asserted

O'Grady submitted his gambling liabilities arose from transactions conducted in circumstances where Benson acted as an unlicensed bookmaker under the meaning of NSW's Unlawful Gambling Act. asserted

Benson (above) was found to have acted as an unlicensed bookmaker, and as such, O'Grady could not be forced to repay any debt he owed him because such gambling was prohibited Judge Nash said there were 'apparently no previously determined cases that have considered the same legal questions' that arose in the case of O'Grady and Benson. 'The issues in this proceeding are therefore novel,' he said. uncertain