Aussie poker legend Gary Benson is in the Australian Poker Hall of Fame, and up almost $3 million according to Hendon Mob, but he’s down AUD $50,000 thanks to a recent loss in court.

A friend borrows money, but can’t repay. It’s a familiar situation that pops up regularly on Twitter, and this time, it’s in court.
We’ll tell you what happened, explaining as quickly as possible.
Gary Bensen & Michael O’Grady’s Wagering
After knowing each other for several years, Gary Benson and Michael O'Grady, a poker pro with around $1.65 million in live earnings, formed a sports betting arrangement.

O'Grady was the bettor, and Bensen was a bit like his backer/manager, approving odds, bets, and extending credit. The pair began tracking their sports betting wagers around May 2022.
The amounts weren't insignificant either, with one bet even reaching A$70,000. Bensen was funding the spreads, and around February 2023, he wanted to collect.

Benson tried to recover A$42,488.58. This comes from a ledger of 211 different transactions from May 2022 to February 2023.
In July 2023, O’Grady was ordered to pay Bensen A$45,035.94. Good news, right?
But for whatever reason, the two poker pros then made a new deal for A$48,711.84, including the July judgment, plus interest. This comes back to bite Benson later on. A key part of this new agreement removed Bensen’s right to enforce the last judgement for A$45,035.94.
Surprise surprise, the arrangement wasn’t honored, and the pair headed back to court. This time, Gary Bensen’s case was completely destroyed.
O'Grady submitted to the court that Benson had acted as an unlicensed bookmaker. Benson, on the other hand, said their relationship “amounted to little more than private betting between acquaintances.”
The court didn't doubt bets were placed, money was owed, or that O'Grady had agreed to repay. But, Magistrate Scott Nash said that after some time, this became “betting activity involving repeated wagering transactions conducted over an extended period.” He ruled that Benson had effectively been operating as an unlicensed bookmaker, and that meant no help from the authorities recovering a single Australian dollar.
“I am satisfied on the balance of probabilities that Mr Benson was acting as a bookmaker within the meaning of the legislation.”
In poker terms, it looks like O’Grady played this situation completely GTO. As for the ethics using a friend’s money for sports betting, not repaying, and getting free of the debt through a crafty loophole, this is looking like a $50,000 angleshoot.
Word to the wise: If you’re a sports bettor, just take the sign-up bonuses and find the best odds online. Skip the arrangements with friends.
- GipsyTeam's unique promotions
- Help with deposits and cashouts
- Access to private freerolls
- Round-the-clock support
- Уникальные акции от GipsyTeam
- Помощь с депозитами и кешаутами
- Доступ в закрытые фрироллы
- Круглосуточная поддержка
How Does a Private Arrangement Become a Betting Operation?
Evidence in the judgment showed the arrangement was far more organized than a couple of friends putting money on the footy.
Under their local law, the person who places a bet and the person who accepts it sit on opposite sides of the regulatory line.

A punter backing a team is doing something ordinary and lawful.
A person who repeatedly accepts bets from others, sets or agrees the odds, runs a book of wins and losses and advances credit is doing the work of a bookmaker, and that activity is licensed for a reason.
Essentially, even though Bensen claimed this was a casual agreement between friends, it doesn’t look that way on paper. It didn’t look like that to the judge either.
The Saddest Part for Bensen? He’d Already Won
$45,035 in Australian dollars, or about USD $32,000. That’s how much Bensen would have collected. He’d already beaten O'Grady in court over this money.
Then, for reasons known only to him and O’Grady, another agreement was struck. It failed, they returned to court, and Bensen lost his rights to any of the money. This must have come as quite a surprise, especially after winning the first time around. He also had to pay legal costs.
O’Grady’s string of losses were actually freerolls, he just didn’t know it while he was making the bets.

Both players have won millions on the felt, but this is still a sizeable loss. AUD $45,000 is a little under half of the average salary for a full time working man in Australia.
Does This Mean Bensen Committed a Crime?
Unlicensed bookmaking can carry some real punishment of up to 2 years imprisonment, up to A$11,000 in fines, or both. However, it must be tried as a criminal case, and this was a civil one.
Thankfully, it looks like Bensen is off the hook, possibly forever. He wasn’t charged with anything. If he was, it would need to be a separate case in a criminal court.
And just because a judge found his relationship with O’Grady to be unlicensed bookmaking, doesn’t mean that a criminal trial is guaranteed. It’s a possibility, but civil and criminal courts don’t overlap in this way in Australia.
But there’s a time limit on this kind of offence. According to section 179 of the Criminal Procedure Act 1986 (NSW), charges would have to be brought within six months of the crime taking place. Bensen and O’Grady’s ledger ran from May 2022 to February 2023, well outside of the six month window.
Perhaps, the punishment was lending a friend thousands and getting nothing back.