Podcast
Sharp or Square
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Betting expert Chad Millman and professional sports gambler Simon Hunter dig into all the spreads for every game, all NFL season long, as they narrow down their five best bets. During football season they share their NFL picks, moneyline parlays, totals, survivor pool picks and more. And during the offseason, Chad and Simon share what the wiseguys are saying, and help you get a leg up on the competition across a variety of sports. So whether you're filling out NFL pool picks with your friends, heading to Las Vegas, or just a fanatic for the NFL Draft, preseason, and the 24/7 football news cycle, make Sharp or Square your best bet all year 'round.
125episodes
Episodes
Newest firstAll episodes
Gambling Stories & the Future of Hollywood with Screenwriter Allan Loeb
Yesterday00:50:02Summary readyToday, 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 -- Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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THE FUTURE OF BETTING PART 2: Sports Betting Strategy, AI and Tax Battles
1w ago00:36:38Summary readyIn 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 -- Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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THE FUTURE OF BETTING PART 1 - Prediction Markets, Scandals & Legal Battles
2w ago00:33:59Summary readyIn 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 -- Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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U.S. Open Golf Betting Preview
2w ago00:32:54Summary readyGolf’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. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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FIFA World Cup 2026 Betting Preview
3w ago00:42:19Summary readyThe 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. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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NBA FINALS GAME 4 BETTING UPDATE: Knicks vs. Spurs
3w ago00:42:11Summary readyAfter 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. Follow on all platforms: / sharporsquare https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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NBA FINALS BETTING UPDATE: New York Knicks vs. San Antonio Spurs
4w ago00:41:57Summary readyAfter 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 Subscribe to Sharp or Square for gambling advice, best bets, and predictions from sports betting experts Chad Millman and Simon Hunter. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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STANLEY CUP FINALS BETTING PREVIEW & NFL TRADE REACTION - Canes vs. Golden Knights, Myles Garrett Trade
4w ago00:47:38Summary readyThe 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. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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NFL WEEK 1 BETTING LINES - 2026 Regular Season Openers
May 2800:54:26Summary readyLet'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 49ers and Los Angeles Rams and a matchup of two AFC playoff hopefuls in Buffalo Bills at Houston Texans. We also get a Super Bowl rematch between the New England Patriots and Seattle Seahawks, and a garbage can affair between the lowly New York Jets and Tennessee Titans. Will Patrick Mahomes return to Kansas City in time to host the Denver Broncos? Will Jaxson Dart put it all together for the New York Giants against the Dallas Cowboys? We get all of our duo's picks and predictions for these mid-September matchups, including their first Big Balls Bet of the Week of the 2026 NFL season! #Volume 0:03:00 - START 0:09:00 - PATRIOTS VS. SEAHAWKS 0:12:00 - 49ERS VS. RAMS 0:14:00 - BROWNS VS. JAGUARS 0:17:30 - JETS VS. TITANS 0:19:30 - RAVENS VS. COLTS 0:25:15 - BILLS VS. TEXANS 0:28:00 - BUCS VS. BENGALS 0:31:15 - BEARS VS. PANTHERS 0:42:00 - FALCONS VS. STEELERS 0:44:30 - SAINTS VS. LIONS 0:48:30 - CARDINALS VS. CHARGERS 0:50:00 - DOLPHINS VS. RAIDERS 0:52:00 - PACKERS VS. DOLPHINS 0:54:30 - COMMANDERS VS. EAGLES 0:57:00 - COWBOYS VS. GIANTS 1:00:00 - BRONCOS VS. CHIEFS-- 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. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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NFL Schedule Release PART 2 with Warren Sharp
May 2600:30:52Summary readyIn 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 discuss reasons for the Cincinnati Bengals to feel hopeful, the NFL priority of ratings over rest, and the woeful drafting of the San Francisco 49ers. #Volume 0:03:00 - START 0:03:40 - BETTING IMPLICATIONS OF NFL SCHEDULE 0:07:15 - LOS ANGELES CHARGERS SCHEDULE 0:10:50 - CINCINNATI BENGALS SCHEDULE 0:14:20 - HOW REST DISPARITY HAS CHANGED 0:31:00 - SAN FRANCISCO 49ERS SITUATION -- 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. Follow on all platforms: https://www.instagram.com/sharporsquare/ https://x.com/SharporSquare_See omnystudio.com/listener for privacy information.
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