Sharp or Square

In the second installment of this two-part episode, we dive into the future of sports betting strategy, artificial intelligence, and the battle between prediction markets and traditional sportsbook operators. Betting expert Chad Millman and professional gambler Simon Hunter discuss the changes in tax laws for sports bettors after the One Big Beautiful Bill Act, and how prediction markets’ unlimited liquidity has impacted the sports betting marketplace. We also hear about how A.I. has made life both easier and harder for gamblers in the last 12 months. And finally, Chad and Simon look into their crystal ball to predict what the next decade holds for the industry. #Volume
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In the first of a two-part episode, we dive into the future of sports betting, online gambling and prediction markets like Kalshi with the help of a special guest. Betting expert Chad Millman and professional gambler Simon Hunter are joined by Chris Gerlacher of Prediction News as they update the audience on everything that has transpired in the last 12 months.
Since joining us last summer, Gerlacher provides updates on the many legal and regulatory challenges Kalshi and other prediction markets have faced across the country. We also touch on prediction market scandals and "insider trading" accusations from within the federal government. Kalshi is a platform that has enjoyed tremendous growth since accepting contracts on sports last January, but will this growth continue? Will the CFTC continue to serve as the regulatory body for the prediction market industry? And what can we expect over the next few years? #Volume
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Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter.
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See omnystudio.com/listener for privacy information.

Golf’s most challenging major returns to the Hamptons! The U.S. Open tees off on Thursday at Long Island’s beautiful Shinnecock Hills Golf Club. Today we cover every betting angle in an episode sponsored by ZBiotics. Go to https://zbiotics.com/SHARPORSQUARE and use SHARPORSQUARE at checkout for 15% off any first time orders of ZBiotics probiotics.
Joining hosts Chad Millman and Simon Hunter is returning guest Spencer Aguiar, a two-time Fantasy Sports Writer Association Golf Writer of the Year, last year’s winner of Research Article of the Year, and one of the smartest golf modelers around. Shinnecock Hills Golf Club is famously beautiful, and landed at No. 5 in Golf Magazine’s Top 100 golf courses in the world. But it can also make for a challenging U.S. Open. What factors stand out when you look at this course? What kind of play will be rewarded or punished? Plus, we look at the odds on fan favorites like Jon Rahm, Rory McIlroy and Scottie Scheffler, plus value in the finishing position markets and in head-to-heads. Everything you need to profit on this year's U.S. Open! #Volume
0:03:00 - START
0:18:00 - BEST BETS FROM TOP OF THE BOARD
0:26:00 - BEST BETS FOR MATCHUPS AND MAKE CUT
0:34:00 - BEST LONGSHOT BETS FOR US OPEN
-- All lines provided by Hard Rock Bet
Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter.
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The wait is over! FIFA World Cup 2026 begins today as the world's top soccer players assemble for the pomp and pageantry of the globe's preeminent sporting event. Spread across North American host sites from coast-to-coast, fans and bettors alike couldn't be more excited. Here to break down all the World Cup action are betting expert Chad Millman and professional gambler Simon Hunter, who welcome soccer expert Anthony Dabbundo of The Ringer. Together they give their top betting picks and predictions for this five-week tournament, including best bets for the Group Stage, Golden Boot, and U.S. Men's National Team. Will Spain or England win it all? Could Argentina or France upset the favorites? And what can we expect from superstars like Kylian Mbappe, Harry Kane, Mikel Oyarzabal, and Erling Haaland? Does Lionel Messi have enough left in the tank to make a run to the Final? Or will Cristiano Ronaldo remind us all why he's one of the greatest soccer players who has ever lived? All these questions answered and more as FIFA World Cup 2026 kicks off today! #Volume
0:03:00 - START
0:19:00 - TOP WORLD CUP CONTENDERS
0:40:00 - U.S. MEN'S NATIONAL TEAM PREVIEW
-- All lines provided by Hard Rock Bet
Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter.
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After a thrilling Game 3 of the NBA Finals in Madison Square Garden Monday night, bettors have a whole new series on their hands! New York is still favored to lift the Larry O'Brien Trophy as we discuss all the best bets for New York Knicks versus San Antonio Spurs.

Betting expert Chad Millman and professional gambler Simon Hunter welcome back NBA expert Jason Timpf of the 'Hoops Tonight' podcast to break down the NBA Finals from a betting perspective, giving us picks, predictions, and the sports betting strategy we'll need to keep profiting during the NBA Finals.

The San Antonio Spurs and star Victor Wembanyama rallied in the second half of Game 3 to cut this series to 2-1 and handing New York its first loss in weeks. Jalen Brunson and Karl-Anthony Towns of the Knicks will now try to capture a home victory in Game 4 as all of New York cheers them on. Is another championship parade in their future? #Volume
0:03:00 -START
0:14:00 - NBA FINALS GAME 3 RECAP
0:31:30 - NBA FINALS GAME 4 BEST BETS
-- All lines provided by Hard Rock Bet
Subscribe to Sharp or Square for gambling advice, best bets and predictions from sports betting experts Chad Millman and Simon Hunter.
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https://x.com/SharporSquare_
See omnystudio.com/listener for privacy information.