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Dan Bilzerian, Bill Perkins Thinking Of Double-Or-Nothing Bets To Follow $1.2M Bike Ride Gamble

High-Stakes Gamblers Eying Even Crazier Endurance Prop Bet


High-stakes gamblers Dan Bilzerian and Bill Perkins are discussing a possible follow-up prop bet to the Las Vegas-to-LA bicycle ride the former completed last week.

Perkins told Card Player in an interview that ideas for the double-or-nothing wager include rowing from England to New York City, walking coast-to-coast across America and climbing Mount Everest. Because Bilzerian completed the last wager, it would be Perkins’ turn.

“Do I really want to lose a nose? I would be very upset if I lost my nose,” Perkins said of the possibility of climbing Everest. “If we have a bet with a 1-in-20 chance of dying I wouldn’t like that."

As for walking across America, Perkins said he’s not sure he would be interested in devoting that amount of time to a bet. Bilzerian’s 300-mile bike ride, which netted him $600,000 from Perkins and hundreds of thousands more in side bets, had to be completed within 48 hours, and he ended up doing it in just 33.

While there was a minor “misunderstanding” between the two about a van that Bilzerian was able to draft behind for awhile, Perkins said Bilzerian’s performance was “quite impressive.” According to Perkins, the vehicle, which was removed about 100 miles from the end of the ride, probably only allowed Bilzerian to save 4-6 hours of time.

“I didn’t agree to vehicle drafting, but I don’t think at the end of the day it would have made a difference," Perkins said.

Bilzerian, a 35-year-old who has suffered heart attacks, spent a lot of money preparing for the ride (more than $100,000), which included a chef and also some coaching from Lance Armstrong. “No chance he would have made it without the help,” Perkins said.

According to Perkins, Bilzerian underestimated the danger of the ride. At one point, when Bilzerian was going about 30 miles per hour down a hill, a chain on his bike came off. Despite that close call and some others, Bilzerian finished basically unscathed. But he did have serious concerns about his health before even beginning.

“Three days before [the ride] he checked into the hospital with chest pain and arm pain," Perkins said. "He didn’t tell anybody, but he checked in. I think he basically got lucky he didn’t get seriously hurt.”

Bilzerian, who is known for his Instagram photos of a playboy lifestyle, won’t be continuing his cycling training. He lost 15 pounds thanks to the bet.

“He hated it,” Perkins said of Bilzerain’s training. Bilzerian said he hadn’t been on a bicycle in 18 years.

Before his bet with Bilzerian, Perkins was the man behind a high-stakes lunging prop bet with poker pro Antonio Esfandiari. The three-time bracelet winner ended up deciding to urinate in a bottle underneath a poker table while competing in January’s PokerStars Caribbean Adventure main event. Esfandiari was disqualified and later apologized for taking the prop bet that far.

Perkins said that while the bet with Bilzerian had “more entertainment value,” it was more expensive than his previous one. But “dollar for dollar, the Antonio bet” was more fun, Perkins said.