Sharp or Square

With NFL Training Camps opening later this month, hosts Chad Millman and Simon Hunter make their early NFL playoff bets in this 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. Every year, teams burst onto the scene. Last season it was the upstart New England Patriots led by Drake May...

What are some of the most entertaining betting and casino movies you've never seen? Today's returning guest is Hollywood talent manager Michael Lasker, who joins hosts Chad Millman and Simon Hunter for a terrific conversation covering sports betting, the rise of the mid-budget Hollywood movie, the concept of "director jail,” and more. Together the trio provide recommendations like ‘Dig...

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...

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’ un...

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, Gerlac...

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 H...

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...

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...

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 t...

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 ex...

Let's the betting begin! With just over 100 days remaining until kickoff of the 2026 NFL regular season, betting expert Chad Millman and professional gambler Simon Hunter examine the betting lines across all 16 games on the NFL Week 1 slate.  Together we hear about the Cleveland Browns as big underdogs against the Jacksonville Jaguars, an Australian divisional game between the San Francisco 4...

In the second part of our episode covering the 2026 NFL regular season release, betting expert Chad Millman and professional gambler Simon Hunter examine more betting angles with data guru Warren Sharp of Sharp Football Analysis. In this episode, our trio looks at the betting implications of rest disparities throughout the league and the terrible hand the Los Angeles Chargers were dealt. They also...

The NFL released the full 2026 regular season schedule last week, with new holiday slates, incredibly consequential prime time matchups and loads of international games. Betting expert Chad Millman and professional gambler Simon Hunter dive into all the implications in a special two-part episode with data guru Warren Sharp of Sharp Football Analysis. In this episode, the trio discusses the legacy...

Only four NBA squads remain in contention for the Larry O'Brien Trophy, as the best basketball teams in the world battle on the hardwood. 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 Conference Finals from a betting perspective. The San Antonio Spurs sent shockwaves across the sporting world...

Before the full 2026 NFL schedule releases tonight, hosts Chad Millman and Simon Hunter are joined by longtime producer Matt Mitchell for a special NFL Mailbag episode. Together they discuss the new contract extension for Miami Dolphins running back De'Von Achane, the Pittsburgh Steelers' drama surrounding Mike McCarthy and Aaron Rodgers, along with Kyler Murray as a Minnesota Viking. We also hear...

Today we bring you the author of one of the world's most epic gambling stories. Award-winning writer Kit Chellel is a reporter for Bloomberg & Businessweek Magazine, where he covers sports betting and financial scandals. His work has been featured in the Wall Street Journal, the Washington Post and the Chicago Tribune, among many other prestigious publications. Most importantly for today, he&r...

This week we dive into the NFL Draft selection of every team in a special two-part episode, wrapping up with today's show covering the AFC. Betting expert Chad Millman and professional gambler Simon Hunter are joined by special guest James Weaver of Sports Info Solution. Together they discuss the picks they loved and hated, including the Kansas City Chiefs trading up for Mansoor Delane, the Las Ve...

This week we dive into the NFL Draft selection of every team in a special two-part episode, starting with the NFC in this 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. Today betting expert Chad Millman and professional gambler Simon Hunter discuss the picks they loved and hated, i...

One of America's most cherished Rites of Spring, the 152nd running of the Kentucky Derby is this Saturday at Churchill Downs in Louisville, Kentucky. This is the perfect event for sports fans and gamblers looking to turn a small investment into a big payday, with limitless opportunities and a massive parimutuel pool. To help them build some winning Kentucky Derby slips, betting expert Chad Millman...

The 2026 NFL Draft is a wrap! From Fernando Mendoza to Mr. Irrelevant, this year's Draft leaves much to discuss in this 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. Betting expert Chad Millman and professional gambler Simon Hunter welcome back NFL Draft betting guru D...

The waiting is over! The 2026 NFL Draft starts TONIGHT in Pittsburgh, as betting expert Chad Millman and professional gambler Simon Hunter welcome back NFL Draft betting guru Derek Brown of FantasyPros to discuss their final player props, betting picks and predictions for the first round and beyond. Today our trio looks at the final offerings in the NFL Drafter betting market, along with analyzing...

The 2026 NFL Draft starts Thursday in Pittsburgh, with fans and gamblers growing more and more invested as the first round approaches. Betting expert Chad Millman and professional gambler Simon Hunter welcome back NFL Draft betting guru Derek Brown of FantasyPros to discuss the betting market and give out their favorite picks and predictions. This episode is sponsored by ZBiotics. Go to https://zb...

The first round of the 2026 NFL Draft is now one week away, as betting expert Chad Millman and professional gambler Simon Hunter welcome back NFL Draft betting guru Derek Brown of FantasyPros. As new betting options continue to emerge, today our trio examines the impact of the latest draft news on the market overall. University of Miami defensive end Reuben Bain has become embroiled in a controver...

The NBA Play-In Tournament tips off tonight, paving the way for the official start of the NBA Playoffs this Saturday. Joining us to discuss all things betting in the NBA Playoffs is the host of Hoops Tonight and our Volume podcast colleague Jason Timpf! Jason joins betting expert Chad Millman and professional gambler Simon Hunter to break down the four established matchups in the first round. In t...

Best-selling author and longtime ESPN writer Seth Wickersham has become an expert on how NFL quarterbacks become elite and how professional teams evaluate the quarterback position. That expertise comes from years hearing it directly from NFL legends like Bill Belichick, Tom Brady, Sean Payton, Steve Young, and others. Today, hosts Chad Millman and Simon Hunter welcome back Seth to discuss his take...