Circles Off - Sports Betting Podcasts

Everyone says AI can help you win at sports betting, but there's a right way and a wrong way to use it. We cover why more context beats a better prompt, why you should always check the steps behind an answer, and how to test a betting idea before you risk anything. Plus, the NFL's latest push on prediction markets at the Supreme Court, viewer questions from our most-watched AI video, and this week...

Sharp bettor Thon Misser breaks down the MLB same game parlay angle that kickstarted his betting career: a pricing bug that turned round number totals into a free half run. He explains how adding any second leg to an over 6 moved the price to over 6.5, why he paired it with an under on triples from hitters who almost never get one, how it played out until a couple of unlucky days and a burned acco...

Victor Wembanyama put his foot down this week, declaring he will never endorse a prediction market or sportsbook. That bold stance opens up a massive conversation about where the line should be drawn when athletes take those exact deals. From there, we jump into a wild NFL Week 4, unpacking the Patriots shocking the Bills and what Lamar Jackson's ankle injury means moving forward. We also react to...

Teams playing on Thursday after a Sunday overtime game are 7-29 against the spread since 2000. I’m not a trends guy, so here’s exactly how I work through a stat like this, step by step: checking how it’s counted, finding the right comparison, looking past the win-loss record, testing the explanation, and asking whether the market’s already on it. This one held up better than most. Here’s why you s...

NFL Week 3 delivered chaos, the Steelers upset the 2-0 Bengals in Pittsburgh, Josh Allen and the Bills survived five turnovers to beat the Chargers, and Drake Maye's turnover problems continued in New England. Over in golf, Team USA pulled off a historic comeback at the Presidents Cup, erasing a four-point deficit to win 17-13 at Medinah for their 11th straight title. Plus reaction to the MLB regu...

Thon Misser joins Off Script to break down the NBA season simulator he's been rebuilding this offseason, how it prices different tiers of players, and what changes after a summer that saw the Raptors add Kawhi Leonard and the Sixers bring in LeBron James. From there the conversation moves into the latest push to bring margin trading to prediction markets and what that means for how those markets g...

Can sharps actually beat a prediction market maker? Chris "Flup" Dierkes breaks down what market makers really do, why new exchanges need in-house liquidity, how auto-movers and traders manage directional risk when the flow hits one side, and what the CFTC's proposed bona fide market making rules could mean for the role. He also takes on the biggest misconceptions, including whether market makers...

NFL Week 2 sports betting reaction gets broken down live on Circle Back, alongside a New York Times report alleging a sportsbook used an AI model to score customers by expected losses and aim bonuses and free bets at them, which the sportsbook disputes. Is +EV overrated? We debate expected value betting and whether the hype matches the results. We also react to Vanderbilt vs NC State and what's be...

A College Football Playoff simulator reveals the real tension in sports betting: when do you trust an algorithm's clean number, and when does a sharp bettor's read on one isolated spot beat the model? Shipper joins Jacob Gramegna for the very first episode of Off Script to break down algorithmic decision-making versus human intuition using live betting, prediction markets, and expected value examp...

The CFTC has proposed new rules that could reshape how market making works across prediction market platforms, from fee treatment for in-house market makers to limits on the positions they're allowed to take. The proposal touches everything from single-market liquidity to how combos and RFQs get priced, and depending on how it's implemented, it could change who's able to compete as a market maker...

The NFL, under Commissioner Roger Goodell, has taken a major step in its evolving relationship with prediction markets, and the crew breaks down what it means for sports betting going forward. Week 1 of the NFL season brought plenty of storylines, including a reality check for the Los Angeles Rams following their 27-7 loss to the San Francisco 49ers, and a betting-adjacent ad campaign featuring Sy...

The LeBron James next-team market became the second-largest market prediction platforms have ever seen, trailing only the World Cup, with over $240 million traded. Peanut, aka Peanut Bettor on Twitter, joins Circles Off to break down how a market this size actually moves — why $500,000 walls formed around teams like Miami and Minnesota, and how a trader decides whether to jump a wall or wait it ou...

Do quants ignore motivation? I tested the most famous motivation angles in football, revenge games and blowout bounce backs, against 20+ years of real NFL closing lines. One of them was legitimately profitable. Then the market found it. This is the full lifecycle of a betting edge, tested live against 20+ years of real NFL closing lines. 🟢 Sponsored by ProphetX, America's #1 Sports Prediction Mar...

Sharp bettor and responsible gaming advocate Isaac Rose-Berman joins Circles Off at BetBash to break down a tennis edge hiding in plain sight. Because of the way tennis scoring works, a player who falls behind by two breaks in a set will often stop competing entirely to conserve energy for the next one, but sportsbooks don't always adjust their in-match pricing to reflect it. Isaac walks through h...

In this episode of Legendary Loopholes, China joins Circles Off to break down one of the most unique player prop edges of the last decade. Starting around 2016, China built a reputation moving college football player prop lines at a major sportsbook, sometimes 60 to 80 props a week. When a second sportsbook entered the market and began scraping those openers days later, it created a two season win...

NFL weekend chaos, Week Zero heartbreak, and plenty of drama. Aaron Donald is back — so what does that mean for the Rams and their futures? Plus, Jacobs lands on the commissioners list, a fantasy league debacle unfolds, and we investigate the very real possibility that the “49ers guy” is completely fake. We break down the brutal Hawaii beat from Week Zero, roast Knish for celebrating way too early...

This week on Circle Back, host Jacob Gramegna is joined by Porter, Isaac Rose-Berman, and Shipper to break down three stories shaking up the prediction markets and sports betting world. The crew dives into a New York Times report that Donald Trump Jr. privately urged a room of Republican state attorneys general to back off regulating prediction markets, arguing that state pushback was being driven...

This episode is presented by ProphetX. Our guest is ProphetX co-founder Jake Benzaquen — we address the relationship directly at the top of the episode. Jake Benzaquen co-founded ProphetX eight years ago, long before "prediction market" was a phrase anyone outside finance used. In June, ProphetX became the first sports-native platform to win CFTC approval as a regulated exchange — and this convers...

Browns recap covering Deshaun Watson's postgame comments after getting booed plus the Sanders update, and Dae'Quan Wright's stunning exit from the NFL back to LSU; Ashton Jeanty's injury scare and what it means for fantasy owners; Scottie Scheffler playing through hand, foot & mouth disease at the BMW Championship and whether golf needs injury reporting; Establish The Run shutting down their pick-...

Prediction markets are having a moment of reckoning. Sharp bettors are starting to call out PM platforms for the same behavior that made traditional sportsbooks notorious: squeezing out the very winners who helped legitimize the space in the first place. From new maker fees quietly eating into sharp profits to a "pro gambler arc" meme capturing the entire cycle of boom, backlash, and burnout, this...

A post about an MIT professor's coin flip (win $125, lose $100) went viral claiming that refusing the bet was the smart move. The psychology is real. The advice is backwards. This is the difference between risk aversion as wisdom and risk aversion as a leak... and the one number from the story that proves it. In this video, Rob breaks down why a single coin flip with a roughly 55% implied win prob...

NFL preseason line movement is under the microscope after a wild stretch of results: teams that have moved 1.5+ points or more on the spread this season are 0-8, and 23-51 since 2024, according to Big Al McMordie's numbers. That trend has reignited a fierce debate about whether closing line value still holds up as a betting principle, with some pointing to small sample sizes and starters entering...

Prediction markets and sportsbooks might look identical on the surface. Same lines, same moneylines, same spreads. But legally and structurally, they're nothing alike. In this conversation, Jacob sits down with Captain Jack Andrews to break down why prediction markets don't meet the legal definition of gambling the way sportsbooks do, walking through the "chance, consideration, and reward" test, t...

Rishi Bets has been posting on X since 2011 with over 35,000 posts and a following nowhere near what that volume would suggest, and it's exactly why the account works. He posts his bet sizes, his wins, and his losses in real time, no cherry-picking. Rob Pizzola sits down with Rishi for a full interview covering his case for prediction markets over traditional sportsbooks, the World Cup position th...

Rob and Jacob were on the ground at Bet Bash 2026 (August 4-7), and they're bringing back the biggest storylines from the event, including the fallout from Steve Fezzik's touting ethics seminar. Geoff missed the trip, and shares his perspective from watching it all unfold from home. The crew also dives into the latest out of the WNBA, from a player's claims of white privilege in the league to Enes...