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The win completely changed his relationship with gambling. In Madsen’s words: “That jackpot was really the beginning of my gambling addiction.”  It was an addiction that was propelled by a constant exposure to illegal sites, he explains.

The cycle eventually became extreme.

“At one point, I had only a few thousand euros left to gamble with, but then I won €180,000 in a single day. The next day I lost it all again,” he says.

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Each Supreme Court term begins on the first Monday in October and runs through late June or early July. The court typically receives about 7,000-8,000 writ petitions and grants about 80, or 1%, each term. Four of the nine sitting justices must vote to accept a case. Five current justices – Chief Justice John Roberts and Justices Clarence Thomas, Samuel Alito, Elena Kagan, Neil Gorsuch and Sonia Sotomayor – were on the bench in 2018 for the PASPA case.

There are no SCOTUS-prediction market contracts currently on Kalshi but Polymarket lists a 41% probability that the court will accept an event contract case by 31 December.

A hearing before the Supreme Court would be the culmination of what has been the biggest sports betting-related development since PASPA. Perhaps no other issue has united gaming stakeholders from various companies, tribes, states and regulators.

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Entain highlighted that 11 of 20 Premier League clubs currently hold sponsorship or advertising arrangements with gambling operators lacking a Gambling Commission license—up from government estimates of eight clubs during the 2025/26 season.

“The government made clear in February that it would bring in a ban and it should do so immediately,” said Entain CEO Stella David, noting that clubs entering new agreements had already been warned. “Inconvenience is not an excuse for inaction.”

Entain cited third-party analysis forecasting that bets placed by UK consumers with unlicensed operators could skyrocket from £17 billion ($22.8 billion) in 2025 to more than £33 billion ($44.2 billion) by 2028 if left unchecked.