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PODCAST

WiseKracks

WagerTalk Media

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

sports sports news

All Episodes

51:30

NFL Divisional Round Bets, Joey Chestnut in Vegas &...

WiseKracks ·

2026/01/15

🎲🏈 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

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44:56

NFL Wild Card Weekend BETS, Casino News & Las Vegas...

WiseKracks ·

2026/01/08

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

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60:53

Final Week of the NFL Regular Season, Casinos in Debt...

WiseKracks ·

2026/01/01

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

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50:45

NFL Week 16 Picks, Poker Battle & Casinos Use Scents...

WiseKracks ·

2025/12/18

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

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57:16

ALAN BOSTON | Handicapping College Basketball, Las...

WiseKracks ·

2025/12/08

🎙️ 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

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43:53

George Martorano on Life, The Mob, Prison & Business

WiseKracks ·

2025/12/04

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

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49:45

NFL Week 12 Picks, Casino Robbed & Broncos Frauds?! |...

WiseKracks ·

2025/11/24

This week on WiseKracks, professional sports bettor Bill “Krackman” Krackomberger checks in from Atlantic City, while Jon Orlando holds things down from the Durango Casino in Las Vegas. Two cities, two coasts, one wild week in the sports-betting world. Krackman reacts to the shocking assassination of Coach John Beam, a tragedy that has shaken the football community. Jon and Krack break down the Broncos’ upset win over the Chiefs — and why Denver still might be a fraud team despite the headline

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47:46

Stu Ungar Stories, Betting College Basketball &...

WiseKracks ·

2025/11/24

Get ready for another must-watch 47-minute conversation with two legendary gamblers — Bill “Krackman” Krackomberger and the incomparable Alan Boston. If you love insider stories, old-school gambling wisdom, and sharp sports betting insight, this episode is loaded. Krackman and Boston dive into: 🎲 Wild stories about Stu Ungar — the brilliance, the chaos, and the legacy 🐎 Betting horses and the characters who shaped the race tracks 💊 Drug use in the gambling world 🧠 How Alan Boston almost became a

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47:33

ALAN BOSTON | Billy Walters Stories, Winning Betting...

WiseKracks ·

2025/11/14

🎙️ Bill “Krackman” Krackomberger x Alan Boston | 47-Minute Deep Dive Into College Hoops Betting & Vegas Stories In this special 47-minute episode, professional sports bettors Bill “Krackman” Krackomberger and legendary college basketball sharp Alan Boston sit down for an honest, unfiltered conversation about life as long-time gamblers, the evolution of college hoops, and what still creates an edge in today’s betting market. Krack and Boston swap classic old-school Las Vegas stories, talk about

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42:24

NFL Week 11 Picks, Gambling News & a $1,000 NFL Future?!

WiseKracks ·

2025/11/14

Welcome back to WiseKracks! 🎙️ Straight from the world-famous Westgate SuperBook in Las Vegas, professional sports bettor Bill “Krackman” Krackomberger and co-host Jon Orlando are bringing the heat for another action-packed episode. This week, Krack and Jon put their money where their mouth is—literally—as they team up for a $1,000 NFL Futures wager. Find out what they bet… and why. They dive deep into the latest headlines rocking the betting world, including: 🔥 MLB pitchers tied to a gambling

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53:59

NFL Week 10 Best Bets, Casino Rip-offs & Lions could...

WiseKracks ·

2025/11/07

🎙️ Welcome back to WiseKracks — filmed live from the iconic SuperBook at the Westgate Las Vegas! This week, professional sports bettor Bill “Krackman” Krackomberger and co-host Jon Orlando dive into a packed episode filled with the latest stories from the world of sports and gambling. ⚾ World Series Recap: The Dodgers and Blue Jays went head-to-head for the title — and Krack & Jon break down every big moment from the Fall Classic. 🎰 Inside the Gambling World: Why some casinos are removing

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46:12

NFL Week 9, NBA Gambling Scandal & Slots in Chicago...

WiseKracks ·

2025/10/30

Professional Sports Bettor and Advantage Gambler Bill "Krackman" Krackomberger and Jon Orlando are live from Las Vegas to talk about what's happening in the gambling world, slot machines coming to Chicago airports, the NBA gambling scandals, the World Series & much more! Randy Lee McKay joins the show to share his best bets for week 9 of NFL action!

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26:28

NFL Week 8, World Series & Today's Gambling News!

WiseKracks ·

2025/10/24

Professional Sports Bettor and Advantage Gambler Bill "Krackman" Krackomberger and Jon Orlando are live from Las Vegas to talk about what's happening in the gambling world, the best blackjack dealer in the world, gambling in Illinois, new shows coming to Las Vegas & much more! Randy Lee McKay joins the show to share his best bets for week 8 of NFL action!

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63:19

He lost $350 MILLION Gambling! Terry Watanabe's FIRST...

WiseKracks ·

2025/10/16

Terry Watanabe joins Bill "Krackman" Krackomberger and Jon Orlando in this week's episode of WiseKracks for his first interview. Watanabe took over his family's company, Oriental Trading, and after he retired lost around $350 million gambling in Las Vegas casinos in just a few years.Later on in the show, Randy Lee McKay joins to share some week 7 NFL picks and Krackman talks about a wild futures parlay that just need the Los Angeles Dodgers to win the 2025 World Series.Time Stamps0:00 - 0:41

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41:08

NFL Week 6, Cheap Live Craps & Wire Fraud?!

WiseKracks ·

2025/10/10

Professional Sports Bettor and Advantage Gambler Bill "Krackman" Krackomberger and Jon Orlando are live from Las Vegas to talk about what's happening in the gambling world, a fraud story in the poker world, gambling on cruises & much more! Randy Lee McKay joins the show to share his best bets for week six of NFL action!

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39:52

Week 5 NFL Picks, Fake Betslips & The Vegas Lifestyle

WiseKracks ·

2025/10/10

Professional Sports Bettor and Advantage Gambler Bill "Krackman" Krackomberger and Jon Orlando get together at the Westgate SuperBook in Las Vegas to talk about what's happening in the gambling world, Jon's crazy day in the casino, scams in gambling & more! Randy Lee McKay joins the show to share his best bets for week five of NFL action!

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43:15

NFL Week 4, Grandissmo Survivor Contest Pick & Teen...

WiseKracks ·

2025/09/27

Professional Sports Bettor and Advantage Gambler Bill "Krackman" Krackomberger and Jon Orlando get together at the Westgate SuperBook in Las Vegas to talk poker, a teen that was arrested for hacking Las Vegas casinos, Krackman's Grandissmo Contest entry, golf and more! Randy Lee McKay joins the show to share his best bets for week four of NFL action!

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45:08

NFL Week 3 Bets, Robbed of $70,000 & QUADRUPLE Zero...

WiseKracks ·

2025/09/18

Professional Sports Bettor and Advantage Gambler Bill "Krackman" Krackomberger and Jon Orlando get together at the Westgate SuperBook in Las Vegas to talk MLB futures, a big WagerWire parlay, getting robbed of $70,000, Gambling Problems, and much more! Randy Lee McKay joins the show to share his best bets for week three of NFL action!

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39:23

NFL Week 2 Picks, Gambling News & Life in Las Vegas

WiseKracks ·

2025/09/11

Professional gambler Bill "Krackman" Krackomberger joins Jon Orlando and Randy Lee McKay talk about week 2 NFL bets, the news in the gambling and sports betting world and much more! 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

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37:06

New House Rules, BIG Slot Winnings & Playing the...

WiseKracks ·

2025/09/04

Professional sports bettor and advantage gambler Bill "Krackman" Krackomberger joins Jon Orlando to talk gambling, what's happening in Las Vegas and plenty more!Time stamps0:00 - 3:42 Poker3:43 - 7:12 Money in the Casino7:13 - 11:09 Draftkings New House Rule11:10 - 12:05 Food Prices12:06 - 14:04 Is Vegas Dead?14:05 - 14:49 Sphere14:50 - 17:17 Powerball17:18 - 18:37 Dana White18:38 - 24:45 Casino Lawsuit24:46 - 26:07 Desert Discovery26:08 - 28:52 Casino Scheme28:53 - 29:50 Venmo29:51 - 37:03 Slots

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