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WiseKracks

WiseKracks

By: WagerTalk Media
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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.WagerTalk Media Politics & Government
Episodes
  • BIZARRE Gambling Stories from WSOP!

    BIZARRE Gambling Stories from WSOP!
    Jun 26 2026
    🎙️ 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.
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    32 mins
  • CRAZY Stories Winning $573,876 with Mark Checkwicz!

    CRAZY Stories Winning $573,876 with Mark Checkwicz!
    Jun 17 2026
    🎙️ WiseKracks Podcast | WSOP Updates, NFL Futures, WagerWire Parlays & The Incredible Story of "Cookie Monster" Mark Checkwicz! Bill "Krackman" Krackomberger and Jon Orlando are back from the World Series of Poker in Las Vegas with another entertaining episode of the WiseKracks Podcast! The guys kick things off with the latest updates from the WSOP, as Jon Orlando shares how he's feeling about his experience at the series so far. Krackman then reveals a few NFL futures bets he's already locked in and breaks down another eye-opening futures parlay discovered on the WagerWire app. Plus, the duo debates what they would do if they suddenly had $10 million in their bank account! At the 18:48 mark, special guest Mark Checkwicz joins the show. Mark won the 2024 WSOP $5,000 Seniors High Roller event for a life-changing payday of more than $500,000. He shares his incredible journey through the tournament, discusses the importance of responsible gambling, explains how he earned the nickname "Cookie Monster," and tells an absolutely CRAZY story about losing the money shortly after winning the tournament. 🔹 World Series of Poker updates from Las Vegas 🔹 Jon Orlando's WSOP experience 🔹 Krackman's NFL futures bets 🔹 WagerWire futures parlay breakdown 🔹 What would you do with $10 million? 🔹 Mark Checkwicz interview (18:48) 🔹 Winning the WSOP Seniors High Roller 🔹 Responsible gambling discussion 🔹 The origin of "Cookie Monster" 🔹 The unbelievable story of losing his winnings Drop a comment below and let us know: What would YOU do with $10 million?
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    56 mins
  • WiseKracks at WSOP talking Vegas Gambling Stories & More!

    WiseKracks at WSOP talking Vegas Gambling Stories & More!
    Jun 11 2026
    Bill "Krackman" Krackomberger and Jon Orlando are back with another episode of WiseKracks, broadcasting from the heart of the action at the World Series of Poker in Las Vegas! The guys kick things off with a WSOP update as Jon Orlando shares his firsthand experiences from the poker tables, the atmosphere around the series, and what life has been like inside the biggest poker event in the world. Then Krackman dives into some of the biggest stories making headlines across Las Vegas and the gambling world, including: 🔫 A troubling series of armed robberies targeting casino patrons around the country 🏒 The Vegas Golden Knights' latest Stanley Cup playoff run and the excitement around Las Vegas 💰 Updates on gambling taxes and what bettors need to know 🎲 Other major stories impacting the gaming industry and Las Vegas Plus, the guys take another deep dive into a wild futures two-leg parlay listed on the WagerWire app and discuss whether it's worth buying, selling, or holding as the sweat continues. If you enjoy sports betting, poker, Las Vegas stories, and behind-the-scenes gambling industry discussions, make sure to subscribe and join the conversation!
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    47 mins
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