One of Australia’s most accomplished professional poker players has failed in a court bid to recover nearly $50,000 in alleged gambling debts from another punter.
Gary Benson, an inaugural inductee into the Australian Poker Hall of Fame, has recorded career earnings of $2,826,031 and sits 20th on Australia’s all-time poker money list.
The 69-year-old has a Wikipedia page and owns a World Series of Poker bracelet, regarded as the most prestigious non-cash prize available on the global poker circuit.
Away from the tables, Benson has worked as a chartered accountant since 1985. For three decades, he specialised in advising Australian poker players about their US tax obligations.
His occasional poker rival, 52-year-old Michael O’Grady, has a lower profile on the tour but remains a successful player in his own right. O’Grady ranks 56th on the Australian money list, with career winnings of $1,657,979.
O’Grady also wagers heavily on sport, including AFL, NRL, NFL, UFC, motor racing, tennis, soccer and golf. Benson was willing to take his private bets.
The Sydney men had known one another for several years before entering an ongoing betting arrangement that eventually brought both before the court.
Benson was ultimately found to have been operating as an unlicensed bookmaker. Because the gambling arrangement was prohibited, O’Grady could not be compelled to repay any money allegedly owed to him.
Gary Benson, one of Australia’s most successful professional poker players, unsuccessfully turned to the courts in an attempt to recover nearly $50,000 in alleged debts from a fellow punter. Benson is pictured.
Gary Benson and Michael O’Grady, pictured above, both compete on the international poker circuit. The pair had known each other for years before their ongoing betting arrangement led to court proceedings.
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.
‘Initially, that relationship appears to have been relatively informal,’ Judge Nash found.
‘However, over time it developed into a sustained course of betting activity involving repeated wagering transactions conducted over an extended period.’
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.
‘This was not a case involving one or two isolated bets,’ Judge Nash found. ‘Nor was it a case involving occasional social wagering.
‘The evidence further establishes that odds were quoted, discussed and agreed. Mr Benson was not merely participating in bets proposed by others.
‘He occupied the position of receiving wagering propositions and agreeing the terms upon which betting would occur.’
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.
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: “Yep”
O’Grady: “Thx Gaz”
‘Outcomes of the wagers were subsequently recorded and liabilities calculated according to those outcomes,’ Judge Nash said.
‘A feature of the parties’ dealings was that liabilities were not invariably settled immediately following the completion of a particular event or wager.
‘Instead, wins and losses were often carried forward and incorporated into an ongoing balance between the parties.’
From time to time, Benson extended credit to O’Grady and ‘the relationship developed characteristics that were financial as well as recreational’.
On one occasion, Benson accepted two wagers totalling $20,000 within about two minutes. The ledger recorded Benson receiving $70,000 in wagers from O’Grady on August 12, 2022.
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
‘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.
‘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.’
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.
‘Discussions concerning repayment occurred and, for a time, the parties attempted to manage the position without recourse to the courts,’ Judge Nash said. ‘Those efforts were ultimately unsuccessful.’
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.
MORE STORY: AI Assistant Instinct’s Valuation Quadruples to $10B in a Month
Judgment 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’.
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.
As part of the undertaking, Benson surrendered enforcement rights of the original judgment and a third man acted as his guarantor.
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.
The case did not turn on whether the debt or compromise agreement existed, but rather whether Benson had been acting as an unlicensed bookmaker.
‘Gambling has become an enduring feature of professional sport and racing,’ Judge Nash said in his judgment.
‘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.
‘Another familiar warning is, “Chances are you’re about to lose”. In a sense, both expressions have some relevance to these proceedings.’
O’Grady and the third man were represented by Tony Taouk, of Magna Carta Lawyers, instructing barrister Cameron Shamsabad.
Benson contended his dealings with O’Grady ‘amounted to little more than private betting between acquaintances’, and the compromise agreement was a binding contract.
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.
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.
‘The novelty of the case lies not in the existence of wagering transactions but in the legal consequences that follow from a later compromise agreement reached after judgment had already been entered and enforcement activity had commenced.’
The Unlawful Gambling Act of 1998 defines a bookmaker as a person ‘who carries on the business of, or who acts as, a bookmaker, bookmaker’s clerk or turf commission agent’.
Alternatively, it states a bookmaker is a person who ‘gains, or endeavours to gain, a livelihood wholly or partly by betting or making wagers’.
If Benson was acting as a bookmaker, his wagering arrangements with O’Grady were prohibited by reason of him being unlicensed. If he wasn’t, O’Grady’s case would fail.
‘I am satisfied on the balance of probabilities that Mr Benson was acting as a bookmaker within the meaning of the legislation,’ Judge Nash found.
Judge Nash did, however, accept Benson’s submission there was no evidence he gained or sought to gain a ‘livelihood’ from wagering transactions.
O’Grady (above) might be less well known on the poker tour than Benson but nonetheless ranks 56th on the Australian money list, with career earnings of $1,657,979
In making those findings, Judge Nash said: ‘In my opinion the relationship extended beyond the realm of private social wagering.’
‘I accept that laying a wager is not itself synonymous with acting as a bookmaker. I accept that no bright line exists between private wagering and bookmaking activity.
‘The finding that Mr Benson acted as a bookmaker is based upon the cumulative effect of the proved conduct and not upon any isolated feature of the relationship.’
That meant the wagering arrangements upon which the compromise agreement depended were prohibited by the Unlawful Gambling Act and it was not enforceable.
‘Mr Benson’s claim fails not because the compromise agreement or guarantee lack contractual validity, but because the legislation denies legal effect to agreements of that character when they derive from prohibited gambling,’ Judge Nash said.
Judge Nash dismissed Benson’s claim, entered judgment in favour of O’Grady and the third man and ordered Benson to pay both men’s costs ‘as agreed or assessed’.
Tony Taouk, the solicitor who acted for O’Grady and the third man, noted a gambling liability and an enforceable debt were not always the same thing.
‘What makes the case particularly interesting is that the outcome ultimately turned on the statutory consequences of prohibited gambling, rather than ordinary contractual principles,’ he said.
‘Once a gambling dispute reaches a courtroom, the issue is no longer simply who won or who lost. The question becomes whether the law will recognise and enforce the resulting liability.
‘The case is a reminder that when gambling arrangements become the subject of litigation, the statutory framework can be just as important as what the parties themselves agreed.’