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Latest Episodes:

NFL TRAINING CAMP QUESTIONS with Ben Solak of ESPN Jul 21, 2026

Show notes

NFL Training Camps begin this week across the NFL! Today we discuss the biggest questions heading into the 2026 season with Ben Solak of ESPN in a special 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.

Ben joins hosts Chad Millman and professional gambler Simon Hunter to discuss the Cleveland Browns under new coach Todd Monken, and the chances of a New England Patriots return to the Super Bowl with MVP candidate QB Drake Maye. We also hear about Patrick Mahomes, Travis Kelce, and a Kansas City Chiefs team flying under the radar this summer. Can the Baltimore Ravens and Lamar Jackson return to the playoffs with new coach Jesse Minter? And are Jaxson Dart and Cam Skattebo savvy enough to carry John Harbaugh's New York Giants back to the Super Bowl? We also hear about the latest data and analytics among the brightest NFL defensive coaching staffs, and whether Chicago Bears' quarterback Caleb Williams is ready to become the next Josh Allen. #Volume

0:03:00 - START

0:05:15 - GUEST BEN SOLAK

0:09:50 - NFL DEFENSIVE TRENDS 2026

0:20:06 - CLEVELAND BROWNS

0:30:00 - NEW ENGLAND PATRIOTS

0:48:00 - KANSAS CITY CHIEFS

0:57:30 - NEW YORK GIANTS

0:58:30 - BALTIMORE RAVENS

0:59:30 - NFC NORTH & CALEB WILLIAMS

-- All lines provided by Hard Rock Bet

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WORLD CUP FINAL BETTING PREVIEW: Spain vs. Argentina Jul 16, 2026

Show notes

It's finally here! The world holds its breath as they await the FIFA World Cup 2026 Final. After a shocking come-from-behind victory over England and star Harry Kane, defending champion Argentina is back in the Final. They'll square off against favored Spain, who defeated superstar Kylian Mbappe and France. Now it all boils down to this incredible World Cup Final on Sunday afternoon in the Meadowlands. Who will be crowned as the world's best soccer team? And more importantly: how can we profit off it?

Stars like Lionel Messi, Mikel Oyarzabal, Lamine Yamal, and Julian Alvarez headline this transhemispheric showdown, as the globe's most spellbinding sporting event reaches its apex. Back 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 picks and predictions for this enormous match, including who they believe will lift the trophy, best bets on player props, and more. #Volume

0:00:00 - START

0:00:30 - ENGLAND VS. ARGENTINA RECAP

0:20:47 - SPAIN VS. ARGENTINA PREVIEW

0:43:00 - BRASS BALLS BET OF THE WEEK -

All lines provided by Hard Rock Bet

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MLB BETTING UPDATE with Sean Zerillo Jul 14, 2026

Show notes

Major League Baseball's annual All-Star Break is here! Time to take step back, take stock, and build some winning bets! Baseball betting and analytics expert Sean Zerillo returns to outline the teams he's buying, the teams he's selling, and the prop bets and exotics he's wagering on for the second half of the MLB season. Together with hosts Chad Millman and Simon Hunter, they tackle the important questions.

Will the Seattle Mariners wake up and run away with the American League West? Will Aaron Judge and the New York Yankees learn some plate discipline, or will the Tampa Bay Rays capture the AL East? Could Bryce Harper and the Philadelphia Phillies make another postseason run? And can Shohei Ohtani and the Los Angeles Dodgers continue their torrid pace through the rest of the summer? Check out this loaded episode for all the best bets, prop betting strategies, player props, and updated season win totals your rawhide heart desires! #Volume

0:00:00 - START

0:10:00 - JUICED BASEBALLS

0:21:00 - DETROIT TIGERS UPDATE

0:27:45 - PITTSBURGH PIRATES, CHICAGO WHITE SOX

0:34:00 - MLB AWARDS BEST BETS

0:38:00 - LOS ANGELES DODGERS UPDATE -

All lines provided by Hard Rock Bet

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NFL PLAYOFF BETTING PREDICTIONS Jul 07, 2026

Show notes

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 Maye. But are they set up to fail this season? What about Joe Burrow and the Cincinnati Bengals? Are the Cleveland Browns circling the drain after trading Myles Garrett, or could they surprise in the AFC? Plus, our guys take a long look at NFC contenders like the Detroit Lions, Los Angeles Rams, and Seattle Seahawks, plus contenders-in-waiting like Jayden Daniels and the Washington Commanders. #Volume

-- 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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Underrated Gambling Movies with Michael Lasker Jul 02, 2026

Show notes

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 ‘Diggstown’ and ‘Mississippi Grind,’ two films very few gamblers are familiar with today. Later, we hear about the rise of the A24 studio and any early Academy Award contenders. #Volume

-- 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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Gambling Stories & the Future of Hollywood with Screenwriter Allan Loeb Jun 30, 2026

Show notes

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

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 FUTURE OF BETTING PART 2: Sports Betting Strategy, AI and Tax Battles Jun 23, 2026

Show notes

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

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.

THE FUTURE OF BETTING PART 1 - Prediction Markets, Scandals & Legal Battles Jun 18, 2026

Show notes

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

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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U.S. Open Golf Betting Preview Jun 16, 2026

Show notes

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.

Follow on all platforms:

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See omnystudio.com/listener for privacy information.

FIFA World Cup 2026 Betting Preview Jun 11, 2026

Show notes

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.

Follow on all platforms:

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See omnystudio.com/listener for privacy information.