WiseKracks

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 han...

🎙️ 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 tru...

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'...

🎙️ 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'...

🎙️ 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...

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. Th...

🎙️ 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. The...

🎙️ 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%...

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 sport...

🎙️ 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...

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...

Welcome back to another episode of the WiseKracks Podcast with pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando! The guys kick things off with a deep dive into the Kentucky Derby from a betting perspective, breaking down how sharp bettors are approaching the biggest race of the year. Plus, Krackman shares an exclusive text from legendary bettor Paul Matties that you won’t hear anywh...

Get ready for another can’t-miss episode of WiseKracks with professional sports bettor Bill Krackomberger and co-host Jon Orlando! This week, the guys kick things off by breaking down the major news surrounding the new partnership between the Westgate SuperBook and Caesars Entertainment, and what it could mean for the future of sports betting in Las Vegas and beyond. From market impact to potentia...

🎙️ 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...

🎙️ 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 worl...

🎙️ 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...

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 ongo...

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, b...

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 Madnes...

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 perspecti...

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...

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...

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...

🔥 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 brea...

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 sto...