WiseKracks

Football contest season is officially here, and Bill "Krackman" Krackomberger and Jon Orlando are back from the Circa Sportsbook in Downtown Las Vegas with another action-packed episode of WiseKracks! The guys kick things off by breaking down the incredible growth of Las Vegas football contests, discussing the massive signup numbers this summer and the important topic of tipping your proxy. How much should you tip if your proxy helps you cash a life-changing prize? Bill and Jon share their thoughts and experiences from years in the contest world. Jon also tells a wild story about meeting someone who hit a...

The WiseKracks crew is back from the iconic Circa Sportsbook in Downtown Las Vegas! Professional sports bettor Bill "Krackman" Krackomberger and Jon Orlando kick off the show by talking about filming inside Circa, wrapping up an exciting summer at the World Series of Poker, and everything happening around Las Vegas. This week's guests are the executive producers behind "Circa Survivor: The Quest for $18.7 Million – Season 3," the hit football contest documentary airing on VSiN, NESN, MSG, and other networks. They pull back the curtain on how the series came together, what fans can expect this season, and why the Circa Survivor co...

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...

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...

🎙️ 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...

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...

🎙️ 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 getti...

🎙️ 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 th...

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...

🎙️ 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 Vega...

🎙️ 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...

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 V...

🎙️ 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 respo...

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 discus...

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 anywhere else. From there, the show turns into a wild ride of Vegas stories and major headlines from around the gambling world: The latest on Mathew Bowyer — the bookmaker tied to Shohei Ohtani’s interpreter — and his addi...

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 potential ripple effects across sportsbooks, Krackman gives his inside perspective from years in the industry. As always, Krackman brings the stories—and this episode is loaded: A shocking casino story involving a mother leaving her child in a ca...

🎙️ 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 casi...

🎙️ 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...

🎙️ 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 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 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...

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 t...

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 hidi...

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 Su...

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...

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 legend...

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 app...

🔥 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 st...

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 —...

🎙️ WISEKRACKS PODCAST – Vegas Stories, Hard Rock Florida, WSOP 2026 & A Bitcoin Takeover?! Pro sports bettor Bill “Krackman” Krackomberger is back with Jon Orlando for another wild ride through the gambling world — and this one covers EVERYTHING from Florida to the Las Vegas Strip 👀 Krackman breaks down his recent trip to the Hard Rock in Florida — what stood out, how the action compares to Vegas, and the behind-the-scenes stories only Krackman can deliver. From casino floor observations to sharp play chatter, this is the real inside look. But that’s just the beginning… This episode also dives into: 🔥 Time capsules at old Las Vegas casinos 🚨 Ident...

🎱 WISEKRACKS PODCAST – POOL LEGEND RODNEY MORRIS + SUPER BOWL RECAP & GAMBLING STORIES 🎲 This week on the WiseKracks Podcast, Pro Sports Bettor Bill “Krackman” Krackomberger sits down with one of the greatest pool players of all time — Billiards Hall of Famer Rodney Morris. Rodney shares incredible stories from his childhood, how he broke into the world of professional pool, and what it was like competing against legends like Efren Reyes and Earl Strickland. From high-stakes action to championship moments, Rodney takes us inside the mental game, the grind, and the lifestyle of elite-level billiards. He also talks about launching a brand-new pool tour — what in...

🔥 WiseKracks is back with another can’t-miss episode! 🔥 Pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando dive into everything happening around Super Bowl LX, betting strategy, and the wild stories that only WiseKracks can deliver. The guys talk Super Bowl betting angles, market movement, and how pros are attacking the biggest game of the year. They also get into some off-the-board headlines, including a Yellowstone star set to portray legendary Vegas figure Benny Binion in an upcoming TV series, Joey Chestnut defending his bagel-eating title in Las Vegas, and why Nevada was recently named the most deceitful state in America. Plu...

In this special bonus episode of the WiseKracks Podcast, pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando are joined by legendary advantage gambler Randy Lee McKay for a deep dive into Super Bowl LX between the Seattle Seahawks and New England Patriots. Randy shares his sharp insights on the big game, including: How he’s looking at Super Bowl LX from a betting perspective Super Bowl props to keep an eye on as the market evolves Key impact players that could decide the outcome Stories and experiences from betting Super Bowls over the years This bonus episode is packed with b...

This week on the WiseKracks Podcast, pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando sit down with one of the most recognizable voices in Las Vegas and gambling culture — Vegas Pauly C. With over 543,000 followers on Instagram and 421,000+ on TikTok, Vegas Pauly C has seen everything Las Vegas has to offer — and he doesn’t hold back in this must-watch interview. 🎰 Topics Covered in This Episode: The best & worst hotel/casinos in Las Vegas Positives and negatives of major Strip & off-Strip properties How price gouging has gotten out of control in Vegas Which casinos still take care of players — and which don’t...

In this episode of the WiseKracks podcast, pro sports bettor Bill Krackomberger and Jon Orlando dive into some of the most talked-about stories in Las Vegas right now—both on and off the betting board. The guys break down the latest progress on the new Hard Rock Casino Las Vegas, how other Strip casinos are reacting, and what it could mean for the future of Vegas. They also share an incredible story about an elderly woman cashing in big at a poker tournament, bust a long-standing Vegas myth surrounding the famous suite from The Hangover, and discuss several Las Vegas sp...

🎲🏈 WiseKracks is back with another loaded episode! 🏈🎲 Pro sports bettor Bill “Krackman” Krackomberger joins Jon Orlando to break down everything happening in the world of sports betting and Las Vegas. The guys dive into betting the NFL Playoffs, discuss who they think will win the Super Bowl, and share insights on how sportsbooks are approaching the postseason. They also touch on Metallica coming to the Sphere, playing poker in Las Vegas, and whether quicker transportation in Vegas could actually become a reality. Plus, Krackman talks about a parlay still alive that needs Miami to win the National Championship, and the crew debates how...

On this episode of WiseKracks, pro sports bettor Bill “Krackman” Krackomberger is joined by Jon Orlando for a wide-ranging gambling conversation that hits everything from poker tables to the sportsbook counter. The guys break down poker stories, scams happening around Las Vegas, tipping etiquette in casinos, and some of the newest shows coming to the Vegas Strip. They also recap how New Year’s Eve went in Las Vegas and dive into another wild futures parlay from WagerWire. 🔥 Special In-Studio Guest 🔥 Randy Lee McKay joins the show IN PERSON to give out his picks for the first round of the NFL Playoffs...

On this episode of the WiseKracks Podcast, pro sports bettor Bill “Krackman” Krackomberger is joined by Jon Orlando for another wide-ranging conversation packed with gambling stories, casino news, and sports betting insight. The guys kick things off by recapping a memorable dinner with Jon’s dad — legendary musician Tony Orlando — and share behind-the-scenes stories you won’t hear anywhere else. They also discuss the Arkansas lottery winner making headlines, news surrounding Barry Manilow’s cancer diagnosis, and break down another wild parlay posted on the WagerWire site. The conversation continues with a deep dive into casinos carrying massive debt, the bizarre Hard R...

On this episode of the WiseKracks Podcast, pro sports bettor Bill “Krackman” Krackomberger and co-host Jon Orlando break down a wild mix of gambling stories, casino news, and betting angles from across the industry. Jon recaps a crazy poker tournament experience, while the guys dive into Atlantic City casino revenue surging in November and what it means for the gambling landscape. They also discuss the IRS releasing a draft proposal to change the $2,000 slot tax threshold, the Powerball jackpot climbing toward $1 billion, and how casinos use scents and psychology to keep players gambling. Plus, the crew reacts to reports of fake...

🎙️ Bill “Krackman” Krackomberger x Alan Boston — 1 Hour of Pure Sports Betting Gold! 🎙️ In this special, hour-long conversation, two legendary gamblers sit down for a deep, unfiltered discussion you won’t find anywhere else. Bill "Krackman" Krackomberger and Alan Boston open up about the art and grind of handicapping college basketball, share stories from the wild old-school days of Las Vegas, and dive into your gambling questions from Twitter/X. Whether you're a seasoned bettor or just fascinated by the minds who’ve lived this life at the highest levels, this episode is packed with insight, honesty, humor, and vintage Vegas energy.

This week on WiseKracks, Bill “Krackman” Krackomberger sits down with a truly remarkable guest — George Martorano, the longest-serving first-time non-violent offender in U.S. history, who transformed decades in prison into a story of discipline, creativity, and reinvention. George was born into a Philadelphia mob family and was sentenced to life without parole in 1984 on drug charges. In this wide-ranging interview, he opens up about his life behind bars, how he survived psychologically. He also dives into the next chapter of his life: 🌿 Building his cannabis brand “The Growfather” 🏢 Growing multiple successful business ventures 🍽️ His love for restaurants and top food spots across the...