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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

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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36:55

Gambling Stories with Comedian Vinnie Favorito

WiseKracks ·

2025/09/02

Professional Sports Bettor Bill "Krackman" Krackomberger and Jon Orlando host comedian Vinnie Favorito to share gambling stories, talk about Vinnie's new show, recap their recent interview with the bookie for Shohei Ohtani's interpreter and much more!

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80:52

Bookie for Ohtani's Interpreter Interview - Mathew...

WiseKracks ·

2025/08/25

Advantage gambler and professional sports bettor Bill “Krackman” Krackomberger and Jon Orlando sit down at the home of Mathew Bowyer for an exclusive interview with the bookmaker for Shohei Ohtani’s former interpreter Ippei Mizuhara. Bowyer sat down for an episode of WiseKracks to tell his story. Bowyer pleaded guilty to running an illegal gambling business, money laundering and false tax returns and is expected to receive a sentence of 17 to 27 months in October.Ohtani's former interpreter Ippei

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51:23

WILD Gambling Stories, NFL Futures & Survivor...

WiseKracks ·

2025/08/14

WILD Gambling Stories, NFL Futures & Survivor Strategy with Steve Fezzik.About Krackman: 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

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23:17

HUGE Finals Bet, Pizza Prices in Vegas & Poker Plans!

WiseKracks ·

2025/06/26

🎰 Gambling Expansion and RisksThe episode opens with a satirical take on gambling's expansion into Times Square, with Crack humorously questioning Al Sharpton’s support and highlighting Jay-Z’s casino ambitions. It transitions into a discussion on responsible gambling, as Crack praises initiatives in New Jersey and Virginia schools teaching students the risks of gambling, referencing his own youthful exposure in North Jersey and racetrack culture.🧠 College Gambling EpidemicCrack criticizes the

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