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?

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Episoder(59)

Derek Stevens Talks Circa Football Contests + College Football Betting Preview & MORE!

Las Vegas legend and Circa owner Derek Stevens joins pro sports bettor Bill “Krackman” Krackomberger and Jon Orlando for a loaded episode of the WiseKracks Podcast! Derek Stevens kicks off the show wi...

7 Aug 46min

Vegas Myths, Jackpot Errors, Tips & Cashing in Vegas Football Contests!

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!...

30 Jul 40min

Las Vegas Football Contests, Sportsbook Robbery & a CRAZY Parlay

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 ...

23 Jul 44min

$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 re...

17 Jul 39min

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'...

10 Jul 52min

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 y...

10 Jul 43min

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,...

3 Jul 41min

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...

26 Jun 31min