Episodes

  • Las Vegas & Gambling News + Aliens Winning the Lottery?!

    Las Vegas & Gambling News + Aliens Winning the Lottery?!
    Apr 15 2026
    🎙️ WiseKracks Podcast with Bill “Krackman” Krackomberger & Jon Orlando This week on WiseKracks, Bill and Jon go remote as Krack heads out on the road to catch some golf — but that doesn’t slow things down one bit. The guys kick things off with a recap of The Masters and dive straight into a packed episode full of wild stories, gambling insight, and industry news. Bill shares some unbelievable stories from the gambling world, including a man who claims he won the lottery THREE times thanks to alien intervention 👀. Plus, the guys break down the latest headlines making waves across the betting and casino space. In this episode: ⛳ The Masters recap & takeaways 🎰 Wild gambling stories you won’t believe 👽 Lottery winner claims aliens gave him the numbers 🚨 FBI releases images of suspects in the Offset casino shooting case 🏛️ Washington D.C. proposes expansion into iGaming 🎲 Growing support for a new Meadowlands casino in New Jersey 🎤 New music residencies and shows coming to Las Vegas 📲 A closer look at a futures parlay from the WagerWire App From outrageous stories to real betting angles, WiseKracks continues to deliver the perfect mix of entertainment and insight from inside the world of gambling.
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    56 mins
  • $10,000 Sports Betting Experiment, The Masters & $300K Stolen From a Vegas Casino?!

    $10,000 Sports Betting Experiment, The Masters & $300K Stolen From a Vegas Casino?!
    Apr 9 2026
    🎙️ WiseKracks Podcast | Vegas Stories, Gambling News & The Masters Begins! Professional gambler Bill “Krackman” Krackomberger and Jon Orlando are LIVE from the SuperBook at the Westgate in Las Vegas for another can’t-miss episode of WiseKracks! From the biggest headlines in Las Vegas to wild gambling stories, this episode is packed with everything happening right now in the sports betting world and beyond. 🏌️‍♂️ The guys kick things off with The Masters Tournament, breaking down what makes Augusta National one of the most iconic venues in sports and why this week is so special for bettors and golf fans alike. 💰 Bill dives into a fascinating story involving The Atlantic writer McKay Coppins, who placed a $10,000 bet as part of a sports betting experiment—what can we learn from it? 🐶 They also react to a bizarre Las Vegas story involving a woman who abandoned her dog at the airport and then missed her court date. 🏛️ With Donald Trump set to visit Las Vegas next week, the guys discuss the buzz around his proposal of “No Tax on Tips” and what it could mean for casino workers and the Vegas economy. 🎰 Plus, more wild Vegas headlines: Employees at Binion’s accused of skimming $300,000 💸 Rumors swirling around the potential cancellation of a mega fight between Floyd Mayweather Jr. and Manny Pacquiao at the Sphere 🥊 New ownership and leadership changes shaking things up at the Rio Casino 🔥 If you love Vegas stories, sharp gambling insight, and behind-the-scenes sportsbook talk—this episode is for you. 📍 Filmed on location at the SuperBook at the Westgate in Las Vegas
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    43 mins
  • Final Four Bets, Casino Robberies & Super Bowl in Las Vegas!

    Final Four Bets, Casino Robberies & Super Bowl in Las Vegas!
    Apr 1 2026
    🎙️ WiseKracks Podcast – Vegas Stories, Final Four Bets & Casino Chaos! 🎰🏀 Professional sports bettor Bill “Krackman” Krackomberger is back with Jon Orlando for another wild episode of WiseKracks—and this one is PACKED with unbelievable Las Vegas stories and sharp betting insight. Krackman shares some absolutely insane stories, including a handful of WILD casino robberies in Las Vegas, plus a jaw-dropping $3 million social media stunt that went down at a Vegas casino. From there, the guys dive into everything happening in and around Sin City—from the best burgers in Las Vegas 🍔 to major news like The Super Bowl returning to Vegas and the growing debate around South Jersey lawmakers opposing casinos outside of Atlantic City. 🏀 With March Madness heating up, Krackman and Jon break down the Final Four games and what bettors should be watching heading into the biggest weekend in college basketball. 💰 Then, advantage gambler Randy McKay joins the show to talk betting strategy and share his thoughts on wagering the Final Four—bringing his sharp perspective and actionable insights. Whether you’re here for the Vegas stories, betting advice, or just the chaos that comes with Krackman, this episode delivers it all.
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    47 mins
  • MASSIVE March Madness Handle in Vegas, Smoking in Casinos & MLB Bets!

    MASSIVE March Madness Handle in Vegas, Smoking in Casinos & MLB Bets!
    Mar 26 2026
    Welcome back to another episode of WiseKracks with professional sports bettor Bill “Krackman” Krackomberger and Jon Orlando, filmed LIVE from Las Vegas! In this episode, Krackman brings the heat with some incredible stories from around the gambling capital of the world. From record-breaking crowds at Allegiant Stadium for Luke Combs, to a jaw-dropping $19.5M Las Vegas mansion listing, and the ongoing debate around smoking in casinos across the country — this episode is packed with wild insights and real Vegas talk. They also dive into the numbers behind massive casino revenue in New York, plus what it’s like experiencing March Madness in Las Vegas from a bettor’s perspective — the energy, the chaos, and the opportunities. On the betting side, the guys shift focus to Major League Baseball, breaking down how they’re approaching the MLB season. Jon Orlando shares his early World Series predictions, including a couple of surprise teams you won’t see coming 👀 Plus, Jon recaps his latest poker tournament run — including a stretch where he was chip leader — and what ultimately went right (and wrong) at the tables. 🔥 Topics Covered: Luke Combs sets attendance record at Allegiant Stadium $19.5M Las Vegas mansion talk Smoking policies in casinos across the U.S. New York casino revenue boom March Madness in Vegas experience MLB betting strategies for the season Jon Orlando’s World Series picks (with sleepers!) Poker tournament recap & lessons learned
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    46 mins
  • March Madness Sweet 16 Bets with Alan Boston & Krackman! | 2026 NCAA Tournament Preview

    March Madness Sweet 16 Bets with Alan Boston & Krackman! | 2026 NCAA Tournament Preview
    Mar 24 2026
    March Madness is heating up 🔥 and we’ve got a FULL Sweet 16 betting breakdown with two of the sharpest minds in the game. Professional sports bettor Bill “Krackman” Krackomberger sits down IN PERSON with legendary handicapper Alan Boston at the SuperBook at the Westgate Las Vegas for an hour-long deep dive into the 2026 NCAA Tournament. Alan Boston goes game-by-game through the entire Sweet 16, breaking down matchups, line value, sharp angles, and where the betting market may be off. If you’re serious about betting college hoops, this is must-watch insight from one of the most respected voices in the space. They also touch on a few NIT matchups, giving quick thoughts and perspective on games flying under the radar. To close things out, Alan Boston answers YOUR questions — responding to comments, giving additional betting advice, and sharing more of his unfiltered opinions. 📍 Filmed at the SuperBook at the Westgate Las Vegas 🎙 Featuring: Bill “Krackman” Krackomberger & Alan Boston ⏱️ What’s inside: Full Sweet 16 betting breakdown (ALL games) Sharp vs public betting insights Line movement & value discussion NIT game quick hits Audience Q&A with Alan Boston
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    52 mins
  • Betting March Madness with Krackman & Randy McKay!

    Betting March Madness with Krackman & Randy McKay!
    Mar 19 2026
    Welcome back to WiseKracks — and this one is straight from the heart of the action at the SuperBook inside the Westgate Las Vegas! Professional gamblers Bill “Krackman” Krackomberger and Randy McKay go LIVE in Vegas to break down every single First Round game of the NCAA Tournament from a true sharp betting perspective. This isn’t your typical bracket talk… this is how the pros attack March Madness. 🏀 In this episode: Full First Round betting breakdown — game by game How the sharp money is shaping the market Randy McKay’s official picks for Round 1 Key angles, line moves, and where the value is hiding What it’s REALLY like watching March Madness in Las Vegas Using casino free play + comps to gain an edge Stories, strategy, and behind-the-counter insights from the SuperBook Whether you're firing on every game or just looking for a few sharp angles, this is must-watch content from two of the most respected bettors in the game.
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    44 mins
  • March Madness 1st Round Bets with Alan Boston & Krackman! | 2026 NCAA Tournament Preview

    March Madness 1st Round Bets with Alan Boston & Krackman! | 2026 NCAA Tournament Preview
    Mar 18 2026
    March Madness has officially arrived—and this one is SPECIAL. For the first time ever, Bill “Krackman” Krackomberger and Alan Boston sit down IN PERSON at the legendary SuperBook inside the Westgate Las Vegas for a full breakdown of the 2026 NCAA Tournament. This is a deep dive with one of the sharpest minds in college basketball betting. 🏀 In this episode: Alan Boston gives his betting perspective on EVERY First Round game Sharp insights on lines, matchups, and market value Where the public is wrong—and where the sharps are attacking How Alan approaches the chaos of March Madness Live atmosphere from the SuperBook in Las Vegas 🎰 🎤 BONUS: We wrap things up with a live audience Q&A, where Alan answers real betting questions from fans inside the book. If you're serious about betting the tournament, this is a must-watch. 📌 Topics Covered: First Round Game-by-Game Breakdown Value vs. Narrative in March Madness Underdogs, Matchups & Line Movement Betting Strategy for the NCAA Tournament Live Q&A with Alan Boston
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    1 hr and 8 mins
  • Betting Conference Tournaments & March Madness with Alan Boston!

    Betting Conference Tournaments & March Madness with Alan Boston!
    Mar 13 2026
    Pro sports bettors Bill Krackomberger and Alan Boston sit down for an in-depth one-hour conversation covering everything happening in college basketball as we head toward NCAA Division I Men's Basketball Tournament. Krack and Boston break down the chaos of college basketball conference tournaments, discussing which teams they believe will make the NCAA Tournament, which programs might get left out, and how sharp bettors approach this critical stretch of the season. Alan Boston also explains how he approaches betting during March Madness, including how the betting market changes, how he evaluates matchups, and the strategies he uses when the entire sports betting world is focused on the tournament. The conversation also goes off the betting board as the two longtime gambling personalities dive into movies, music, and stories from their decades around Las Vegas and the sports betting world. They also announce that Alan Boston will be in Las Vegas next week, and they share details about where and when you can watch the next show live in person, giving fans the chance to meet Krackman and Boston and be part of the conversation. If you enjoy sharp sports betting insights, March Madness talk, and great gambling stories, this is an episode you don’t want to miss. Topics covered in this episode include: Betting college basketball conference tournaments Which teams will make the NCAA Tournament Alan Boston’s March Madness betting approach How betting markets change during tournament season Movies, music, and off-the-board conversation Alan Boston coming to Las Vegas next week Details on the next live show with Krack & Boston Subscribe for more interviews, betting insight, and stories from the world of sports gambling.
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    1 hr and 4 mins