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
  • WiseKracks from the World Series of Poker! | Las Vegas Gambling Stories

    WiseKracks from the World Series of Poker! | Las Vegas Gambling Stories
    Jun 3 2026
    🎙️ WiseKracks Podcast LIVE from the World Series of Poker in Las Vegas! 🎲♠️ This week, professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando are broadcasting from the heart of the action at the World Series of Poker. Jon shares his experience from the WSOP so far, including what it's like competing among thousands of poker players chasing life-changing payouts in Las Vegas. Then, Krackman breaks down some of the biggest stories making headlines in Las Vegas and the gambling world, including: 🐎 A shocking horse stabbing incident at South Point Casino 🎰 A self-excluded casino patron who still managed to hit a jackpot 💰 Las Vegas casinos winning a staggering $689 million in April despite a decline in visitor numbers 📰 Other major gambling and casino industry stories from around the country Plus, the guys dive into another outrageous futures parlay listed on the WagerWire app, discussing whether it's worth buying, selling, or simply admiring from afar. If you love sports betting, poker, Las Vegas news, casino stories, and gambling industry insights, this episode is packed with everything you need. 📍 Recorded from Las Vegas during the World Series of Poker
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    31 mins
  • What's Happening in Las Vegas, World Series of Poker & a New Sports Betting Law?!

    What's Happening in Las Vegas, World Series of Poker & a New Sports Betting Law?!
    May 27 2026
    🎙️ On this episode of WiseKracks, pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando kick things off with a heated debate over poker tournament rake structures before previewing their plans for the upcoming World Series of Poker in Las Vegas! ♠️💰 Krackman also shares some unbelievable gambling stories and dives into the latest headlines from around the gaming world including: 🎰 75% of people reportedly having a positive view of Las Vegas 🍔 A secret menu arriving at the World’s Largest In-N-Out Burger 🎟️ The New York Lottery unveiling a brand new slogan 🚨 Growing concerns after another murder at a Kansas City casino 📖 A brand new Louisiana sports betting law 🌡️ The World’s Tallest Thermometer officially going up for sale …and much more! If you love sports betting stories, Vegas news, poker talk and gambling industry headlines, this is an episode you won’t want to miss.
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    43 mins
  • Prediction Markets, Draftkings Wrigley Closing & Buying a Futures Parlay?!

    Prediction Markets, Draftkings Wrigley Closing & Buying a Futures Parlay?!
    May 20 2026
    Bill “Krackman” Krackomberger and Jon Orlando are back with another episode of WiseKracks breaking down the latest stories from around the gambling world! 🎲🔥 This week, Krackman shares the wild story behind his attempt to buy a futures parlay from WagerWire and reveals another WagerWire parlay bettors should keep an eye on right now. The guys also dive into some of the biggest headlines in sports betting and casino news including: 🏈 DraftKings exploring the growing trend of prediction markets 🏟️ The DraftKings retail sportsbook at Wrigley Field shutting down 🎬 “Casino” leaving Netflix 🎰 Atlantic City gambling continuing to thrive 🛗 17 tourists getting trapped inside an elevator at the Rio in Las Vegas 📈 The latest buzz from around Vegas and the betting industry As always, Krackman and Jon mix gambling insight, Vegas stories, sportsbook talk, and plenty of laughs along the way.
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    43 mins
  • Krackman's WILD Stories, New TV Show on Gamblers, Dana White's Letter to the President

    Krackman's WILD Stories, New TV Show on Gamblers, Dana White's Letter to the President
    May 14 2026
    🎙️ The WiseKracks Podcast is back with another wild episode featuring professional sports bettor Bill “Krackman” Krackomberger and Jon Orlando! With the World Series of Poker right around the corner, Jon explains why THIS might finally be his year to make a deep run — while Krackman shares stories, strategy, and what it really takes to survive the WSOP grind in Las Vegas. The guys also break down some of the biggest gambling headlines making noise across the country, including: 🔥 The Evel Knievel Caesars Palace Fountain Jump returning for a Las Vegas dayclub opening 🎰 New Jersey moving to limit sportsbook promos in the name of responsible gambling 📺 A new TV show centered around problem gamblers ⚠️ New York warning the public about unregulated gambling markets 📈 The rise of prediction markets in Las Vegas and across the United States 🇺🇸 Dana White reportedly writing President Donald Trump about undoing the 90% gambling loss deduction cap Plus, Krackman and Jon take a look at another insane parlay from the WagerWire app and discuss whether it’s genius… or just plain crazy. If you love sports betting stories, Las Vegas news, poker talk, gambling industry headlines, and sharp bettor insight — this episode is for you. 📍 Hosted by Bill “Krackman” Krackomberger & Jon Orlando 🎲 New WiseKracks episodes covering sports betting, Las Vegas, casino stories, poker, and gambling culture
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    50 mins
  • Nevada Casinos Closing, $12.8M Lottery Ticket & Cannabis Delivery to Vegas Casinos?

    Nevada Casinos Closing, $12.8M Lottery Ticket & Cannabis Delivery to Vegas Casinos?
    May 8 2026
    Welcome back to another episode of the WiseKracks podcast with professional sports bettor Bill “Krackman” Krackomberger and Jon Orlando! The guys kick things off with a hilarious discussion after Jon didn’t invite Krackman to a baseball game, which quickly turns into one of the funniest arguments the show has had in a while. From there, the conversation shifts into some of the biggest gambling and Las Vegas headlines making waves right now. Krackman dives into the shocking news surrounding casinos closing down in Primm, Nevada, and what it says about the future of certain gambling markets. The guys also discuss Spirit Airlines potentially going out of business, the growing talk of marijuana delivery services coming directly to Las Vegas casinos, and the unbelievable story behind a $12.8 million Arizona Lottery ticket. As always, Krackman shares behind-the-scenes gambling stories, Vegas insight, sportsbook talk, and plenty of wild opinions you won’t hear anywhere else. If you enjoy gambling stories, Las Vegas news, sports betting insight, and uncensored conversations, make sure to LIKE, COMMENT, and SUBSCRIBE for more WiseKracks episodes every week!
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    50 mins