Parlays, Insider Trading, Fertitta and Sinner Factor in This Week’s Gambling Industry Bingos & Busts
Let's recap some of the top stories in the gambling business this week.
Prediction markets continue to dominate the gambling industry news cycle, as parlays, insider trading and President Trump keep making headlines .
The NBA, whose Finals tip off next Wednesday, is also top of mind. The league is taking steps to fix tanking, a phenomenon with sports betting ramifications, and a scrappy gambling operator is having fun with a promotion at the expense of one of the game’s best players.
Additionally, a sports and gambling business magnate is close to completing a long-sought acquisition that could ripple throughout the industry, and the French Open delivers a shocking upset.
Here’s a look back at the highs and lows of this week’s news:
Bust: Kalshi Can’t Hide From Reality of Parlays
While Kalshi and its proponents push the notion that sports is accounting for a decreasing share of overall trading volume, they’re conveniently omitting parlays from the equation. Gambling industry observers aren’t letting them get away with such subterfuge. Per Dustin Gouker, parlays, which are pretty much all sports, comprise about a quarter of the volume on the exchange, and while the company denies it was at the behest of Kalshi, Dune has put datasets revealing how much money customers are losing on “combos” behind a $40,000 paywall, Sportico’s Dan Bernstein reported. Also, according to data cited by Citizens analyst Jordan Bender, retail users are losing 45% more on prediction market combos than on sportsbook parlays – -18% ROI vs. -12% ROI. Meanwhile, we’re all still trying to figure out how parlays offer economic utility.
Bingo: Second Polymarket Insider Trader Taken Down
Michele Spagnuolo, a Google software engineer, has been charged by federal authorities for insider trading after the Italian citizen profited more than $1.2 million from bets related to the most searched terms of 2025. Yes, while Polymarket is victory-lapping over the fact that it flagged the suspicious activity six months ago and is finally realizing that insider trading is an existential threat to its business, the company bears blame for offering markets so susceptible. But the reality is anytime money is at stake, bad actors will try to take it, and catching perpetrators has to be a deterrent to potential future transgressions. Spagnuolo is the second Polymarket trader in as many months to be busted for using inside information – U.S. soldier Gannon Ken Van Dyke, who allegedly profited $400,000 from the capture of Venezuelan President Nicolás Maduro, was charged in April.
Bust: Trump Flip-Flops on Prediction Markets
President Trump wasn’t too comfortable with the Van Dyke news mentioned above, responding then to a question about prediction markets, “I was never much in favor of it,” belying the CFTC’s laissez faire approach to the asset class. A month later, that stance appears to be more headfake than about-face. On his Truth Social platform Wednesday, Trump offered a full-throated endorsement of prediction markets, asserting the CFTC must maintain “exclusive authority” over the industry, while insulting as “scum” opponents Chris Christie, Letitia James,Tim Walz, and JB Pritzker. While the White House says it’s reviewing the CFTC’s proposed new rules governing prediction markets, it’s difficult to envision a tightening of the reins.
Also read: Trump Criticizes the Prediction Markets His Administration Defends
Bingo: Fertitta Wins Bid for Caesars Entertainment
In a $17.6 billion deal that includes $11.9 billion in debt, Tilman Fertitta emerged victorious in his bid to acquire Caesars Entertainment, beating out Carl Icahn and others. With plans to take Caesars private, Feritta’s influence in the gambling industry expands, adding the iconic brand to a portfolio that also houses Golden Nugget and Wynn Resorts (regulatory approval pending). While he faces headwinds of declining tourism in Las Vegas, insurmountable competition in online sports betting and the growing threat of prediction markets, Fertitta has reached the finish line of a quest he started in 2018 with an acquisition bound to shake up the industry.
Bingo: NBA Overhauls Draft Lottery To Combat Tanking
Watching a third of the league prioritize draft position over winning this season, NBA Commissioner Adam Silver knew tanking was an issue that had to be addressed, and a new system formally announced this week goes a long way toward disincentivizing teams from trying to finish lower in the standings. While tanking resulted in historically high point spreads and cat-and-mouse games between bookmaker and bettor, nobody will argue that non-competitive games between contenders and also-rans is good for the sport.
Bingo: Underdog Has Fun With SGA’s Flopping
Underdog is refusing to abide by a cease-and-desist letter from Shai Gilgeous-Alexander’s lawyer demanding the company halt a promotion that playfully digs at the two-time MVP. The Oklahoma City Thunder star has taken plenty of heat this postseason for flopping – the act of exaggerating to draw foul calls – and Underdog saw an opportunity. The prediction market and DFS operator created a board game titled “Unethical Hoops”, based on the Hasbro classic “Operation”, where the player has to guard SGA without touching him. Underdog says it’s an equal opportunity offender, telling Front Office Sports, “We’ve poked fun at Knicks and Lakers fans, the Red Sox owners, the Mets, and more. We like to have some fun with whatever is in the sports fan zeitgeist.” The promotion culminates today, with Underdog giving away 100 copies of the game, and we give the brand kudos for creative, entertaining and engaging marketing.
Bust: Texas Tech Denied Request for Sorsby’s Reinstatement
If the NCAA’s ruling holds up, Brendan Sorsby appears headed for the NFL’s Supplemental Draft. The governing body denied Sorsby’s request for reinstatement after he was ruled permanently ineligible for betting on Indiana when he was a member of the team in 2022. It’s great that Sorsby, who transferred from Cincinnati to Texas Tech ahead of the upcoming season, is taking care his gambling problem, but his excuse that he bet the Hoosiers to feel closer to the team while he was not playing didn’t fly with observers like ESPN’s Rece Davis, and it’s hard to see the NCAA’s decision being reversed.
Bust: Sinner’s Historic Meltdown Proves There’s No Guaranteed Money
When the No. 1 seed led 6-3, 6-2, 5-1 in the second round of the French Open against 56th-ranked Juan Manuel Cerundolo, a bet on Jannik Sinner looked even more like a lock than his -5000 pre-match odds implied. But Sinner cramped up, said after the match he hadn’t been feeling well, and in his words “hit the wall,” dropping 18 of the last 20 games en route to a five-set defeat. It marks one of the biggest upsets in sports betting history, per Yahoo Sports’ Ben Fawkes. While one gutsy bettor saw his $50,000 wager on Sinner blasted all over the internet, he appears unfazed, winning $55,593 on an $80,000 Spurs moneyline bet Thursday night and continuing to “pick up money off of the ground.”
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