Sharp or Square

Sharp or Square

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.

Episodes

May 5, 2026 51 mins

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, including the L.A. Rams trading up f...

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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 and professional gambler Simon Hun...

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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 Derek Brown of FantasyPros to d...

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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 any potential trades. Plus,...

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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://zbiotics.com/SHARPORSQUARE and use SH...

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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 controversy surrounding a fatal car crash fr...

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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 the Eastern Conference those matchup...

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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 on the 2026 NFL Draft class...

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The 2026 NFL Draft approaches as host Chad Millman and professional gambler Simon Hunter welcome back NFL Draft betting expert Derek Brown of FantasyPros.

Before the Las Vegas Raiders are "on the clock" with the No. 1 overall pick in Pittsburgh on April 23rd, our trio looks for gambling value as a few new betting markets continue to leak out. Today they examine player prop bets and make their picks and predictions on what to...

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The Final Four is set! The final weekend of the 2026 Men's NCAA Basketball Tournament tips off this Saturday as the Illinois Fighting Illini face the UConn Huskies, while the Michigan Wolverines square off against the Arizona Wildcats. Betting expert Chad Millman and professional gambler Simon Hunter welcome back college basketball bettor Joshua "Duck" Nunn of the Big Bets On Campus podcast to break the games down for our gambling ...

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March 31, 2026 45 mins

In just three weeks NFL fans will witness the first pick of the 2026 NFL Draft, which takes place in Pittsburgh on April 23rd. Indiana quarterback Fernando Mendoza is the presumed No. 1 overall pick for the Las Vegas Raiders, but after that chaos awaits for fans and gamblers alike! Host Chad Millman and professional gambler Simon Hunter welcome NFL Draft betting expert Derek Brown of BettingPros.

Derek is the co-host of the Fantasy...

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The second week of the 2026 Men's NCAA Basketball Tournament tips off with the Sweet 16 on Thursday and Friday, as teams look to punch their tickets to Elite 8 weekend. Betting expert Chad Millman and professional gambler Simon Hunter welcome back college basketball bettor Joshua "Duck" Nunn of the Big Bets On Campus podcast. Duck provides his best bets for the Sweet 16, including college basketball picks and predictions for underd...

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Spring is in the air and that means Opening Day of the 2026 Major League Baseball season is finally here! Betting expert Chad Millman and professional sports bettor Simon Hunter return to talk all things betting for across MLB, welcoming Payoff Pitch podcast host Sean Zerillo back to the show! Together Chad and Simon talk to their favorite baseball analytics guru about Shohei Ohtani and the juggernaut Los Angeles Dodgers, and wheth...

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March 19, 2026 49 mins

After looking at the 10 highest win totals two weeks ago, betting expert Chad Millman and professional gambler Simon Hunter return with more picks and predictions for the 2026 NFL season! And today we wrap up our two-part episode on win totals looking at the other 22 teams across the National Football League. In this episode, our hosting duo discusses the Minnesota Vikings with new quarterback Kyler Murray, and the new-look Pittsbu...

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One of the greatest weeks of the gambling calendar is upon us! Tipoff of the 2026 Men's NCAA Basketball Tournament looms, as play-in set the table for 32 incredible games Thursday and Friday, spread across host sites nationwide.

Like all red-blooded American gamblers, betting expert Chad Millman and professional gambler Simon Hunter will be partaking in the fun. They've already filled out their brackets in our new free-to-play cont...

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In a podcast tradition unlike any other, preeminent Hollywood insider and Academy Awards savant Michael Lasker joins Chad Millman and Simon Hunter to preview all things betting for Hollywood's biggest night. A longtime talent manager at Mosaic, Lasker has joined the show annually for half a decade now, sharing his wisdom about the Oscars with his photographic memory covering every major category. This year, nominees battling for Be...

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NFL free agency is underway, and the movement has been fast and furious! Today NFL expert Chad Millman and professional sports bettor Simon Hunter are joined by veteran ESPN writer and personality Bill Barnwell to react to all the offseason action.

Tua Tagovailoa was cut by the Miami Dolphins, and will suit up for the Atlanta Falcons this season. Maxx Crosby was the centerpiece of a blockbuster trade from the Las Vegas Raiders to t...

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Larry Bird has one of the most unlikely paths to superstardom in the history of the National Basketball Association. On today's episode, New York Times best-selling author Keith O'Brien explains just how preposterous Bird's rise was. From southern Indiana nobody to legendary basketball icon, O'Brien lays it all out in his freshly-released book HEARTLAND: A FORGOTTEN PLACE, AN IMPOSSIBLE DREAM, AND THE MIRACLE OF LARRY BIRD.

...

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NFL free agency officially begins next week, so betting expert Chad Millman and professional gambler Simon Hunter look ahead to next season! Today we kick off our two-part episode on early 2026 NFL season win totals.

In this episode, our hosting duo discusses the highest win totals on the board, as ten familiar NFL franchises are currently installed with win totals of 10.5 at Hard Rock Bet. Can the Buffalo Bills stay afloat in the ...

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The Winter Olympics in Milan Cortina end this weekend, but not before even more thrilling action on the slopes and at the rink! Betting expert Chad Millman and professional gambler Simon Hunter are joined by producer Matt Mitchell as they discuss all things Winter Games.

Together they discuss the deal skier Eileen Gu forged with China, along with the controversy that has taken the international curling world by storm. We also hear ...

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