Episodes

  • 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
  • STUNG by Scorpion in Vegas Casino, $180K Baccarat Cheating Plot & March Madness!

    STUNG by Scorpion in Vegas Casino, $180K Baccarat Cheating Plot & March Madness!
    Mar 11 2026
    Step inside the wild world of sports betting and Las Vegas stories on this episode of the WiseKracks Podcast with professional sports bettor Bill “Krackman” Krackomberger and Jon Orlando. Krackman delivers another round of unbelievable gambling and Vegas stories, including a shocking incident involving a poisonous scorpion that stung a Las Vegas visitor inside their hotel room. The guys also dive into the impact of the controversial “Big Beautiful Bill” and what it could mean for gambling, plus how bettors are approaching March Madness in Las Vegas sportsbooks. The conversation also travels through some classic and modern gambling stories—from the legendary Benny Binion’s Las Vegas home, to a $180,000 Baccarat scam pulled off by a coordinated group of 11 people, and a troubling trend of carjackings happening in the parking lot of Delaware Park Casino. They also break down major gambling industry news, including a New Jersey horse racing track proposing a massive casino resort, Georgia lawmakers backing off a sports betting referendum, and an important betting discussion on whether buying points in sports betting is ever worth it. As always, Krackman mixes sharp betting insight with unforgettable gambling stories you won’t hear anywhere else. If you love sports betting stories, Las Vegas history, gambling industry news, and sharp betting discussions, this episode is for you. Topics in this episode include: Poisonous scorpion stings Las Vegas hotel guest The “Big Beautiful Bill” and its potential impact on gambling Betting March Madness in Las Vegas sportsbooks The legendary Benny Binion Las Vegas home $180K Baccarat scam involving 11 people Carjackings at Delaware Park Casino parking lot New Jersey racetrack proposing a casino resort Georgia lawmakers folding on a sports betting referendum The truth about buying points in sports betting And more wild stories from Krackman Subscribe for more episodes of WiseKracks, featuring the sharpest minds and wildest stories in the world of sports betting.
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    1 hr
  • NCAA Tournament Bets, Potential Cinderellas & the Mob in Las Vegas | ALAN BOSTON & KRACKMAN

    NCAA Tournament Bets, Potential Cinderellas & the Mob in Las Vegas | ALAN BOSTON & KRACKMAN
    Mar 6 2026
    Legendary sports bettors Bill “Krackman” Krackomberger and Alan Boston sit down for another fascinating hour of stories, betting insight, and classic Vegas history. The show opens with an incredibly sad and shocking story involving the flamingos at the Flamingo Las Vegas, setting the tone for a conversation that moves from wild Vegas moments to serious college basketball betting talk. Alan Boston dives deep into college basketball and the road to the NCAA Tournament, sharing his thoughts on which teams he believes will make the tournament… and which teams will be left out on Selection Sunday. Boston also breaks down how he approaches betting conference tournaments, where sharp bettors often find some of the best edges of the entire season. Along the way, Boston shares old-school Las Vegas stories from the mob era, giving a glimpse into what gambling culture was like in the city decades ago. The conversation also takes a fascinating turn into one of the most talked-about gambling topics in tournament betting — whether bettors have ever received information about basketball rims at college tournament sites and how much that could potentially impact shooting and totals. Finally, Boston discusses whether there are any true longshots with a real chance to make a deep run in March Madness, and what bettors should look for when hunting for a Cinderella story. If you love sharp betting insight, classic Vegas gambling stories, and March Madness strategy, this is a conversation you won’t want to miss.
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    1 hr
  • Vegas Slot Machines, Tourist STEALS a Flamingo & Maxx Crosby Trade Odds

    Vegas Slot Machines, Tourist STEALS a Flamingo & Maxx Crosby Trade Odds
    Mar 6 2026
    🔥 The stories are WILD on this episode of WiseKracks with pro sports bettor Bill “Krackman” Krackomberger and co-host Jon Orlando. Krackman opens the show with one of the most unbelievable Vegas stories you’ll ever hear — a Canadian tourist who allegedly stole one of the live flamingos from the Flamingo Hotel & Casino in Las Vegas. Yes… an actual flamingo. 🦩 Only in Vegas. The guys also break down some major gambling and sports topics including the continued growth of online casino and sports betting revenue, the possibility of MLB games being played in Las Vegas, and the latest buzz around Las Vegas Raiders star Maxx Crosby and his odds to be traded. Plus, Vegas entertainment keeps getting bigger as Metallica continues to add more shows at the Las Vegas Sphere, and the guys talk about how the Sphere has quickly become one of the most talked-about venues in the world. Jon also shares the full story behind his wild poker tournament run this week, including the swings, big hands, and everything that went down at the table. ♠️ To close the show, legendary advantage gambler Randy Lee McKay joins the podcast to talk about betting college basketball, the upcoming tournament chaos, and what bettors should be looking for this time of year. This episode is packed with Vegas stories, gambling insights, poker drama, and college basketball betting talk. 📌 Topics include: A Canadian man stealing a flamingo from the Flamingo casino 🦩 Online casino & sports betting revenue growth MLB playing games in Las Vegas? Maxx Crosby trade odds discussion Metallica adding more Las Vegas Sphere shows Jon Orlando’s crazy poker tournament story Randy Lee McKay on betting college basketball
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    42 mins
  • Turning in $20 MILLION, NEW Vegas Sphere Shows & $12.8 MILLION Arizona Lottery Ticket

    Turning in $20 MILLION, NEW Vegas Sphere Shows & $12.8 MILLION Arizona Lottery Ticket
    Mar 3 2026
    Welcome back to another episode of the WiseKracks Podcast with pro sports bettor Bill Krackomberger (aka “Krackman”) and Jon Orlando! This episode is PACKED with wild gambling stories, Vegas headlines, and behind-the-scenes insights from one of the sharpest minds in the business. 🎙️ On This Episode: Krack recaps his recent shows with legendary bettor Alan Boston — including some classic Boston stories and betting philosophy that only comes from decades in the game. A breakdown of Krackman’s recent trip through Florida and South Carolina — what he saw, who he met, and the betting scene out there. Tales from the poker tables in Las Vegas — the swings, the characters, and why live poker still hits different. A WILD story from Caesars Palace that could turn into a potential lawsuit 👀 Major Vegas entertainment news: Metallica signing to play at the Las Vegas Sphere Boxing mega-news: Floyd Mayweather Jr. vs. Manny Pacquiao at the Sphere?! Slot machine sessions and the psychology behind chasing jackpots 🎰 A CRAZY lottery ticket story you won’t believe And Krackman closes the show with an unbelievable story about a family turning in nearly $20 million to the U.S. government — wait until you hear how that unfolded. From sports betting strategy to Vegas chaos, high-stakes poker, casino drama, and unbelievable real-life gambling stories — this episode has it all.
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    42 mins