WiseKracks
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.
Episodes
October 22, 2026 • 43 mins
WiseKracks is LIVE from the iconic Circa Sportsbook in downtown Las Vegas! Professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando welcome special guest Mike Palm, Vice President of Circa, for another episode packed with wild gambling stories, Las Vegas headlines, sports betting insights and NFL Week 7 best bets! This week, Krack breaks down one of the craziest stories in sports betting: a contestant in the $100,00...
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Mark as Played
October 16, 2026 • 40 mins
NFL Week 6 best bets, wild Las Vegas gambling stories, casino scandals and more! 🎰🏈 Pro sports bettors Bill "Krackman" Krackomberger and Randy McKay are joined by poker player Jon Orlando for another entertaining episode of WiseKracks! The guys kick things off discussing the MLB Postseason before Jon Orlando shares updates from his recent poker tournaments, including stories from his latest poker trip to Canada! Krackman then div...
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Mark as Played
October 8, 2026 • 53 mins
NFL Week 5 is here, and pro sports bettors Bill "Krackman" Krackomberger and Randy McKay are back for another episode of WiseKracks! Randy shares his THREE BEST BETS for Week 5 of the NFL season, while the guys discuss NFL betting strategies, futures wagers, sportsbook limits and much more!Randy also gives an update on his $100,000 Circa Grandissimo contest entry and shares his thoughts on betting the NFL this season. Plus, the guy...
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Mark as Played
October 1, 2026 • 41 mins
WiseKracks is LIVE from Circa Sportsbook in downtown Las Vegas with professional sports bettors Bill “Krackman” Krackomberger and Randy McKay! Krackman kicks off the show with some of the biggest stories making headlines in the gambling and sports betting world. The guys discuss whether underage gamblers should face punishment, some of the huge concerts coming to Las Vegas, and a wild $132,000 craps cheating scheme. The...
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Mark as Played
September 24, 2026 • 32 mins
Another episode of WiseKracks is here with professional sports bettors Bill “Krackman” Krackomberger and Randy McKay!Krackman kicks off the show with some of the biggest and most interesting stories from the world of gambling, including the wild story of an Illinois man who won over $1 BILLION in the lottery — and didn’t even know it! The guys also discuss special Las Vegas deals available this time of year,...
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Mark as Played
September 16, 2026 • 33 mins
🏈 NFL Week 2 is here, and WiseKracks is back with best bets, college football picks and plenty of gambling stories! Professional sports bettor Bill “Krackman” Krackomberger kicks off the show solo by recapping his recent trip to Pennsylvania to bet sports, including his experience getting action down. Krackman also shares details on a special offer for his sports betting picks package and breaks down a parlay from the ...
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Mark as Played
September 10, 2026 • 41 mins
🏈 Football betting is in full swing, and WiseKracks is back with another action-packed episode! Professional sports bettor Bill “Krackman” Krackomberger is joined by Randy McKay to recap a WILD week of college football betting and look ahead to College Football Week 2 and NFL Week 1. Randy kicks things off by reliving TWO absolutely brutal bad beats on his Western Michigan and South Dakota State bets. Randy and Krack b...
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Mark as Played
September 2, 2026 • 47 mins
🏈 Football season is here, and WiseKracks is back from Circa Sportsbook in Downtown Las Vegas! Pro sports bettor Bill “Krackman” Krackomberger is joined by Randy Lee McKay, who breaks down his favorite betting picks and angles for Week 1 of the college football season. Randy shares the games he’s targeting, where he sees value on the board and what bettors should be watching as college football gets underway. Ran...
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Mark as Played
August 26, 2026 • 42 mins
🎰 WiseKracks is back from Circa Sportsbook in Downtown Las Vegas! Pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando kick off this episode by remembering the legendary Dolly Parton. Jon shares some incredible personal stories about meeting Dolly when she performed alongside his father, Tony Orlando, and reflects on the memories he has from those encounters. From there, the guys turn their attention to foot...
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Mark as Played
August 20, 2026 • 70 mins
🎙️ SPECIAL INTERVIEW: Jay Cohen Joins WiseKracks Pro sports bettor Bill “Krackman” Krackomberger sits down for an exclusive one-on-one interview with Jay Cohen, co-founder of World Sports Exchange (WSEX) and one of the original pioneers of online sports betting. Long before online sportsbooks became a massive part of the sports world, Cohen and his partners launched World Sports Exchange from Antigua in the 1990s. WSEX...
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Mark as Played
August 19, 2026 • 53 mins
🎰 WiseKracks is back at Circa Sportsbook in Downtown Las Vegas!Pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando are back for another episode packed with sports betting, gambling news, Las Vegas stories, food talk and plenty of laughs.Krackman kicks things off by making Jon an offer he might not be able to refuse — a piece of Krackman’s Circa football contest entries! The guys break down the o...
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Mark as Played
August 16, 2026 • 51 mins
🎙️ BONUS EPISODE of the WiseKracks Podcast! Pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando sit down with two fascinating guests for an episode packed with incredible stories, business talk, pizza, Las Vegas and a life story you have to hear to believe. 🍕 Albert Scalleat, businessman and owner of Dom DeMarco’s Pizzeria & Wine Bar in Las Vegas, joins the show to talk about his journey in the r...
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Mark as Played
August 16, 2026 • 32 mins
🎰 WiseKracks is back from the Circa Sportsbook in Downtown Las Vegas! Pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando are back for another episode packed with gambling talk, wild Las Vegas stories, sports betting and much more. Krackman kicks off the show with a special offer from Treasure Island that could get you $200 in FREE casino play! From there, the guys dive into some of the craziest stories mak...
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Mark as Played
August 6, 2026 • 46 mins
Las Vegas legend and Circa owner Derek Stevens joins pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando for a loaded episode of the WiseKracks Podcast! Derek Stevens kicks off the show with an inside look at Circa’s massive football contests for the upcoming season. Are signups ahead of pace? How big can these contests get? And why is Circa willing to spend so much money running multiple high-stakes f...
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Mark as Played
July 30, 2026 • 40 mins
Football contest season is officially here, and Bill "Krackman" Krackomberger and Jon Orlando are back from the Circa Sportsbook in Downtown Las Vegas with another action-packed episode of WiseKracks! The guys kick things off by breaking down the incredible growth of Las Vegas football contests, discussing the massive signup numbers this summer and the important topic of tipping your proxy. How much should you tip if your proxy hel...
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Mark as Played
July 23, 2026 • 44 mins
The WiseKracks crew is back from the iconic Circa Sportsbook in Downtown Las Vegas! Professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando kick off the show by talking about filming inside Circa, wrapping up an exciting summer at the World Series of Poker, and everything happening around Las Vegas. This week's guests are the executive producers behind "Circa Survivor: The Quest for $18.7 Million – Season 3,"...
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Mark as Played
July 17, 2026 • 39 mins
The World Series of Poker may be winding down, but the stories are just getting started! 🎲♠️ On this episode of WiseKracks, professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando recap the past few weeks spent playing events and hanging around the World Series of Poker in Las Vegas. Jon shares what it's been like documenting the entire experience through his WSOP vlogs, while Krackman reflects on everything that ...
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Mark as Played
July 10, 2026 • 52 mins
Bill "Krackman" Krackomberger and Jon Orlando are back with another episode of WiseKracks from the World Series of Poker in Las Vegas! After spending weeks at the WSOP, Krackman and Jon share what it's really like playing poker's biggest event. Krackman explains how his opinion of the World Series of Poker has evolved over the years, while Jon breaks down his own tournament experience, biggest hands, and what he's learned during hi...
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Mark as Played
July 9, 2026 • 43 mins
🎙️ 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 Sit...
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Mark as Played
July 3, 2026 • 41 mins
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 ch...
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Mark as Played
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