Today, hosts Chad Millman and Simon Hunter welcome back a very special guest. Allan Loeb is a longtime Hollywood writer and producer with credit spanning over a dozen feature films, including Things We Lost In The Fire, Here Comes The Boom, Wall Street: Money Never Sleeps, and the popular 2008 blackjack film 21 starring Kevin Spacey. Chad and Simon talk to Allan about his time in Hollywood and the future of artificial intelligence in the entertainment industry. We also hear about Allan's arduos history with gambling, including the time he accidentally left $100,000 in cash on an airport train car, outlined in his terrific recent essay in The Free Press here.

#Volume

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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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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

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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

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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

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After a thrilling Game 1 of the NBA Finals, the best teams in world square off again on Friday night. But only one will lift the Larry O'Brien Trophy! Today we discuss all the best bets for New York Knicks versus San Antonio Spurs in this episode hosted by betting expert Chad Millman and professional gambler Simon Hunter. They welcome back NBA expert Jason Timpf of the Hoops Tonight podcast to break down the NBA Finals from a betting perspective, giving us all the gambling picks and predictions we'll need to profit from this exhilarating series.

The San Antonio Spurs sent a clear message across the basketball world with an electrifying performance in the Western Conference Finals, defeating the defending champion Oklahoma City Thunder in seven games. But superstar Victor Wembanyama was a little underwhelming in the first game of the Finals on Wednesday night. Do the favored Spurs have what it takes to defeat the New York Knicks, the winners of 12 consecutive games? In the Eastern Conference Finals, Jalen Brunson and Karl-Anthony Towns punched the New York Knicks' tickets to the NBA Finals with a commanding sweep of the overwhelmed Cleveland Cavaliers. They followed that up with a gutsy come-from-behind double-digit victory in Game 1. Chad and Simon ask Jason Timpf the biggest questions on the minds of NBA bettors as these teams battle on. #Volume

0:03:00 - START

0:06:00 - JASON TIMPF JOINS

0:12:45 - NBA FINALS GAME 1 REACTION

0:24:03 - NBA FINALS GAME 2 BETTING PREVIEW

0:37:40 - NBA FINALS SERIES PROPS AND BEST BETS

-- All lines provided by Hard Rock Bet

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The Vegas Golden Knights and Carolina Hurricanes square off in the Stanley Cup Finals, and today we'll cover all the betting angles 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.

Before we dive into all the hockey betting action in the battle for Lord Stanley's Cup, betting expert Chad Millman and professional gambler Simon Hunter discuss the massive trades in the NFL this week. The Los Angeles Rams traded Jared Verse and a trove of draft picks to the Cleveland Browns for two-time NFL Defensive Player of the Year Myles Garrett in a shocking move Monday. In addition, the Philadelphia Eagles finally traded wideout A.J. Brown to the New England Patriots in a trade long speculated by the media and insiders. Will this be what puts the Rams back in the Super Bowl? And will this be the missing piece for the New England Patriots?

Meanwhile on the ice, guest Michael Leboff of the New York Post offers his best bets, picks and predictions for the Carolina Hurricanes versus Vegas Golden Knights, including pick for the Conn Smyth Trophy and Game 1 tonight in Raleigh. #Volume

0:03:00 - START

0:04:30 - AJ BROWN TRADE REACTION

0:13:50 - MYLES GARRETT TRADE REACTION

0:31:37 - STANLEY CUP FINALS 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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