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Wise Kracks Guest Phil 'The Poker Brat' Hellmuth Has Never Had a Losing Year Betting NFL Totals

Written by: Bill Krackomberger
Updated October 14, 2022
8 min read

If you are a fan of the World Series of Poker (WSOP), then you already know the name Phil Hellmuth, a 2007 inductee in the WSOP Hall of Fame who holds the records for most WSOP cashes (148) and the most WSOP final tables (64), overtaking T. J. Cloutier for that honor.

Known as the ‘Poker Brat’ for his occasional ‘dramatic outbursts’ at the table, Hellmuth has won 15 WSOP bracelets and is our special guest on this episode of WSN’s Wise Krack’s podcast with hosts Bill Krackomberger and Jon Orlando.

Hellmuth, the 56-year-old WSOP champ from Madison, WI, has accumulated live tournament winnings exceeding $24,000,000 (ranked 21st on the all-time money list) and now makes his home in Palo Alto, CA.

Whenever a household name like Phil Hellmuth is a guest of Wise Kracks, co-host Bill Krackomberger of course wants to know how they got their start.

When Krack asks Phil what his life was like before the spotlight began shining, the WSOP champ paints a humble picture.

“I’m the oldest of five, my father had a Ph.D. and I had ADD, and I couldn’t get the grades my dad wanted. [My younger siblings] did that… My own self-esteem then rested on whether I could win at games. In college [at the University of Wisconsin–Madison] I dropped out [after three years] for poker.”

Hellmuth describing his journey to greatness is worth listening to in full, but he shares how he began to set goals for himself to achieve along the way.

“It happened in one night… I created a pyramid for what I had to do to become the best in the world at poker and I set myself on that. I wrote down my lifetime goals, number one: become the greatest poker player of all time… Within a year, year and a half, I won the World Series of Poker main event.”

Co-host Jon Orlando first met Phil right after the Kentucky Derby, when Jon got up the nerve to approach the famous “poker brat” despite understanding that it might not go over well, and Jon was shocked to discover Hellmuth was one of the nicest guys he had ever met.

Phil gets a knowing smile on his face whenever his ‘reputation’ as a disruptive diva comes up since he of all people understands what a total act it actually is.

“The poker world knows I’m one of the nicest guys in the poker business, which is great, but unfortunately the world does not understand that. So when I took the role of poker brat, whether intentionally or not, I always figured it made me a lot more famous, because people remember the bad boys.”

In a pro poker world filled with shady characters and questionable choices, what makes Phil such a good guy?

“I always figured that by 2007, the world would figure out that I’m the nicest guy. I’m the guy that’s not an alcoholic, I’m the guy that doesn’t do drugs, I’m the guy that’s loyal to his friends and nice to everybody. And, of course, no one figured it out yet, and it’s 2021 now.”

And in perfect Hellmuth fashion, the gambling guru succinctly sums up the rub his reputation causes:

“It’s very weird to feel like you’re one of the nicest guys in the poker world and have a lot of people out there think I’m an a—hole.”

In fact, the extremely approachable Phil met his best friend, Chamath Palihapitiya (Sri Lankan-Canadian-American venture capitalist, engineer, SPAC sponsor and the founder and CEO of Social Capital) when the billionaire approached him while he was out eating and invited him to play poker in Palo Alto with them.

“They play 5-10, and that’s like social poker, and I play poker for a living. The stakes are nothing. But I went over, and I just love the group. Chamath crushed me at poker when we were playing very small stakes…”

When it comes to gambling in general, apparently Phil Hellmuth has the golden touch in more than just the poker arena.

When Krack asks Phil about a quote attributed to him where he claims to have never had a losing year of NFL totals, Mr. Hellmuth shares a quick recap of his win streak, including when it started.

“That’s my thing! I’ve won every single year, ever since Peyton Manning went to the Broncos. I’ve won ten years in a row betting NFL totals. To me, something always stands out on the board. My only issue is that I haven’t bet enough. I’m still betting $10,000.”

Listen to more of Wise Kracks for weekly sports betting tips from professional sports bettor Bill Krackomberger and his co-host Jon Orlando.

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Bill Krackomberger

187 Articles

Billy “Krackman” Krackomberger has made his living as a professional sports gambler for nearly three decades. You have seen him on ESPN, Gaming Today, and SiriusXM. His connections in the sports gambling industry run all the way to the top. His bets move the lines and regularly have him banned from books for being too sharp. Email: [email protected]

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