WiseKracks

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.

  1. 8 hrs ago

    $2.2M Jackpot, WSOP Wrap Up & Playing Blackjack!

    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 makes poker season in Vegas unlike any other time of year. The conversation then shifts to some classic Vegas gambling topics, including the mystery memorabilia lucky boxes popping up around casinos, playing blackjack, and whether those tempting side bets are actually worth your money. Krackman also breaks down some of the biggest headlines in the gambling world: FanDuel purchasing a Bryce Harper Cameo for a customer after a heartbreaking losing bet Why the FIFA World Cup is expected to be huge for Las Vegas sportsbooks The latest tax news impacting sports betting Google's tighter restrictions on gambling advertisements The incredible story of a Las Vegas gambler hitting a $2.2 million jackpot And plenty more gambling and Vegas news As always, the guys dive into another interesting parlay posted on the WagerWire app, discussing the strategy and whether they'd make the same bet. Krackman also reveals the brand-new filming location for future episodes of WiseKracks. If you love sports betting, poker, Las Vegas, gambling stories, and behind-the-scenes conversations from the gaming industry, this is an episode you won't want to miss.

  2. Jul 10

    Madness at the WSOP, Current State of Sports Betting & WILD Vegas Stories

    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 his time at the tables. The conversation then shifts to the current state of sports betting. Krackman reflects on how the industry has changed since he first started betting professionally, why he wouldn't want his own child to become a professional sports bettor, and how today's betting landscape is dramatically different. He also discusses why betting baseball has changed, the explosion in popularity of parlays, and how sportsbooks have adapted over the years. As always, the guys dive into some of the biggest gambling and Las Vegas headlines, including: 🎰 The infamous Vegas casino "black list" 🪄 A magician accused of running a casino scam 📰 A Buddhist monk sentenced to 12 years in prison after a gambling-fueled sextortion scandal To wrap up the show, Krackman and Jon break down another intriguing parlay from the WagerWire app, and Krackman lets viewers know where they can find all of his latest betting picks on the WagerTalk website.

  3. Jul 10

    Mob Stories, Gambling in Sports & World Series of Poker! | JEFF NADU

    🎙️ 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 Sitdown with Jeff Nadu. He shares incredible mob stories, behind-the-scenes experiences from producing the show, and why organized crime history continues to fascinate audiences. The conversation also dives into Jeff's long-running rivalry with Barstool personality Rico Bosco, whether the two could ever work together on a future show, and what really happened behind the scenes. Krackman, Jon, and Jeff also break down the latest gambling scandals surrounding both the NBA and college sports, discussing what these incidents mean for the future of sports betting and the integrity of the games. The guys also talk about their experiences playing in the World Series of Poker, including Krackman revealing that a sponsor put up $10,000 for him to play. To wrap up the show, Krackman shares a featured parlay from the WagerWire app centered around several New York teams. 🔔 Topics Include: Jeff Nadu's transition from Barstool Sports to The Sitdown Fascinating Mafia and organized crime stories Jeff's rivalry with Rico Bosco Could Jeff and Rico ever do a show together? NBA and college sports gambling scandals Playing the World Series of Poker Krackman's $10,000 sponsored WSOP entry Krackman's WagerWire New York teams parlay If you enjoyed the episode, be sure to LIKE, SUBSCRIBE, and leave a comment with your favorite Jeff Nadu story or who you'd like to see on WiseKracks next!

  4. Jul 3

    Alan Boston talks Poker, Gambling Stories & Betting Sports!

    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 changed from a bettor's perspective. He also shares his thoughts on the current state of the gambling industry, what bettors should be paying attention to, and where he believes the betting world is headed. Plus, Alan tells hilarious gambling stories from years past, including playing slot machines and shooting craps alongside comedy legend Rodney Dangerfield. Whether you're a seasoned sports bettor, poker fan, or simply love hearing incredible gambling stories from one of the sharpest minds in the business, this is an episode you won't want to miss. In this episode: 🎾 Alan Boston's thoughts on betting Wimbledon ♠️ Playing in the World Series of Poker in Las Vegas 🏈 The changing landscape of college sports 📈 The current state of sports betting and gambling 🎰 Classic casino stories from Alan Boston 🎲 Playing craps with Rodney Dangerfield 💰 Gambling insights from one of the industry's most respected bettors

  5. Jun 26

    BIZARRE Gambling Stories from WSOP!

    🎙️ 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.

  6. Jun 17

    CRAZY Stories Winning $573,876 with Mark Checkwicz!

    🎙️ 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?

  7. Jun 11

    WiseKracks at WSOP talking Vegas Gambling Stories & More!

    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!

  8. Jun 3

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

    🎙️ 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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About

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.

Information

  • Creator
    WagerTalk Media
  • Years Active
    2025 - 2026
  • Episodes
    56
  • Rating
    Explicit
  • Copyright
    © WagerTalk Media
  • Show Website
    WiseKracks

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