Professional sports bettor and advantage gambler Bill "Krackman" Krackomberger joins Jon Orlando to cover what's going in Las Vegas, from gambling stories, big bets, and everything in between.Bill Krackomberger, widely known as "Krackman," isn't just a sports bettor—he's one of the industry's most respected voices and successful handicappers. With decades of experience dissecting betting markets and exploiting edges, Krackman has consistently turned profits by targeting opportunities most bettors overlook.Featured prominently on Showtime’s acclaimed sports betting series "Action" and a regular contributor to VSiN, ESPN, Fox Sports, and SiriusXM, Krackman has established himself as a trusted expert whose advice is sought by novices and professional gamblers alike.
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Podcast Overview
Professional sports bettor and advantage gambler Bill "Krackman" Krackomberger joins Jon Orlando to cover what's going in Las Vegas, from gambling stories, big bets, and everything in between.Bill Krackomberger, widely known as "Krackman," isn't just a sports bettor—he's one of the industry's most respected voices and successful handicappers. With decades of experience dissecting betting markets and exploiting edges, Krackman has consistently turned profits by targeting opportunities most bettors overlook.Featured prominently on Showtime’s acclaimed sports betting series "Action" and a regular contributor to VSiN, ESPN, Fox Sports, and SiriusXM, Krackman has established himself as a trusted expert whose advice is sought by novices and professional gamblers alike.
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Publishing Since
6/26/2025
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Recent Episodes
July 10, 2026
Mob Stories, Gambling in Sports & World Series of Poker! | JEFF NADU
🎙️ Jeff Nadu Joins WiseKracks! Mob Stories, Barstool Drama, Gambling Scandals & WSOP! This week on WiseKracks, professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando are coming to you from the World Series of Poker in Las Vegas with special guest Jeff Nadu! Jeff discusses his journey from becoming a well-known personality at Barstool Sports to launching his own successful true-crime and Mafia podcast, The Sitdown with Jeff Nadu. He shares incredible mob stories, behind-the-scenes experiences from producing the show, and why organized crime history continues to fascinate audiences. The conversation also dives into Jeff's long-running rivalry with Barstool personality Rico Bosco, whether the two could ever work together on a future show, and what really happened behind the scenes. Krackman, Jon, and Jeff also break down the latest gambling scandals surrounding both the NBA and college sports, discussing what these incidents mean for the future of sports betting and the integrity of the games. The guys also talk about their experiences playing in the World Series of Poker, including Krackman revealing that a sponsor put up $10,000 for him to play. To wrap up the show, Krackman shares a featured parlay from the WagerWire app centered around several New York teams. 🔔 Topics Include: Jeff Nadu's transition from Barstool Sports to The Sitdown Fascinating Mafia and organized crime stories Jeff's rivalry with Rico Bosco Could Jeff and Rico ever do a show together? NBA and college sports gambling scandals Playing the World Series of Poker Krackman's $10,000 sponsored WSOP entry Krackman's WagerWire New York teams parlay If you enjoyed the episode, be sure to LIKE, SUBSCRIBE, and leave a comment with your favorite Jeff Nadu story or who you'd like to see on WiseKracks next!
July 3, 2026
Alan Boston talks Poker, Gambling Stories & Betting Sports!
Professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando welcome legendary sports bettor Alan Boston to WiseKracks for an entertaining conversation filled with gambling stories, poker, sports betting, and Boston's unique perspective on today's betting landscape. Alan discusses betting Wimbledon, his experience playing in the World Series of Poker (WSOP) in Las Vegas, and how today's college sports environment has changed from a bettor's perspective. He also shares his thoughts on the current state of the gambling industry, what bettors should be paying attention to, and where he believes the betting world is headed. Plus, Alan tells hilarious gambling stories from years past, including playing slot machines and shooting craps alongside comedy legend Rodney Dangerfield. Whether you're a seasoned sports bettor, poker fan, or simply love hearing incredible gambling stories from one of the sharpest minds in the business, this is an episode you won't want to miss. In this episode: 🎾 Alan Boston's thoughts on betting Wimbledon ♠️ Playing in the World Series of Poker in Las Vegas 🏈 The changing landscape of college sports 📈 The current state of sports betting and gambling 🎰 Classic casino stories from Alan Boston 🎲 Playing craps with Rodney Dangerfield 💰 Gambling insights from one of the industry's most respected bettors
June 26, 2026
BIZARRE Gambling Stories from WSOP!
🎙️ WiseKracks Podcast | WSOP Updates, Crazy Gambling Stories & Vegas Headlines! Bill "Krackman" Krackomberger and Jon Orlando are back from the World Series of Poker in Las Vegas with another episode of the WiseKracks podcast! The guys kick things off with the latest updates from the WSOP, as Jon shares how his daily vlogs from the series have been going and what it's been like covering poker's biggest event from the ground. Then Krackman dives into some of the wildest gambling stories making headlines, including: An update on the Terry Rozier gambling investigation North Carolina raising taxes on online sportsbooks A player getting 86'd from the World Series of Poker for smoking The shocking story of 17 horses killed in a fire at Saratoga A Las Vegas woman arrested after allegedly marrying 14 men in a money scam And plenty more bizarre stories from the gambling world! If you enjoy sports betting, poker, Las Vegas news, and unbelievable gambling stories, this is an episode you won't want to miss.
54 total episodes available
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