Four Richest Professional Gamblers in the World

There are those who like an occasional flutter with a friend on the winner of the Superbowl, and there are those that take their gambling very seriously. Then there are those who make a professional career out of gambling and do so very successfully. Some feel it is immoral to gamble but fail to see that the people employed on Wall Street effectively live off gambling. Like one gambler was reported to have bet $1.21 million on Floyd Mayweather to win at -500 moneyline. Instead of gambling on sports, they’re gambling on companies’ success.

Richest Professional Gamblers in the World

• Zeljko Ranogajek
• Bill Benter
• Phil Ivey
• Annette Obestrad

We look at a few of gambling’s success stories but remember, these are the people we know about, and those who keep the lowest of profiles may have racked up much, much more.

Zeljko Ranogajek

Billionaire Zeljko Ranogajek is considered to be the world’s biggest gambler, and the fact that he’s a mathematician may tell you that his luck lies in ensuring he minimizes the chances of losing. Ranogajek started life on the Australian island of Tasmania, the son of Croatian parents, studying commerce and law before teaming up with a friend to take on the casinos. The pair used mathematical analysis to win big on Blackjack and poker and it wasn’t long before they came to the attention of the casino owners and were banned. They traveled to the US where they continued to win before being banned again.

At around this point, Ranogajek turned his focus to horse racing but his betting was never random in nature. He employed teams of mathematicians, statistical analysts, veterinarians, and trackside observers – what was called ‘the Bankroll’. The statistics piled up and betting only occurred when certain criteria were met.

The bets he was involved with were so big that he was receiving favorable discounts and rebates from betting pool operators. As he stated himself, the plan was “you bet to lose, so that you turn over more money and the win comes from rebates…If you bet $100 and lost $5, but you get a 10 percent rebate, you still make five percent.” It was estimated he’d earned about $52m over three years betting on US races with only around 15 percent coming from winning bets.

Bill Benter

The legend that is Bill Benter is now a lecturer, a philanthropist and a man who was so good at winning he turned down a $13m windfall. Benter hailed from Pittsburgh and was a successful Blackjack player and, like many big winners, fell foul of the Vegas casinos. He was forced to widen his gambling horizons and teamed up with Australian Alan Woods to great success. Woods knowledge of horse racing combined with Benter’s computer and mathematical skills produced a formula to choose winners. The formula is deemed by many as the ultimate in racing and is believed to have netted Benter around $1bn in winnings.

The infamous $13m tale involves a win on the Triple Trio, a legendary bet on the Hong Kong races. It involved picking the top three finishers in three different races and rolls over when it is not won. In 2001 the pot stood at around $13m when one winning ticket took the prize. Benter is alleged to have decided it “unsporting” to claim it and, knowing the money would go back into racing merely kept the ticket in a safe. The fact he was already very very rich must have made the decision far easier but he talked about the win in a rare interview for Bloomberg – the gambler who cracked the horseracing code

Phil Ivey

Phil Ivey may be a name you don’t recognize, but to those that follow poker, he is one of the game’s biggest names. Born in California, Ivey grew up in New Jersey where he developed his skills playing against his work colleagues as a teenager, before using a fake ID to play poker at Atlantic City. He came to prominence in 2002 winning three bracelets at the World Series of Poker WSOP – equaling the most in a single year. His skills saw him in high demand with many of the world’s richest men eager to pit their wits against him in cash games. In 2006 he played Texas Hold’em against Texan billionaire Andy Beal, Ivey winning over $16m over the course of three days. He also famously won the biggest online cash game with a pot of over $19m.

Annette Obestrad

It might be their preference to keep a low profile, but the names of high-profile female gamblers are particularly hard to find, But with testosterone very much part and parcel of the poker world, it is reassuring to know that there are numerous women who have shown they are more than a match for their male counterparts. The youngest winner of WSOP bracelet in the year they were first played outside the US was an 18-year-old from Norway, more than two years before she would be legally allowed to play on the Vegas tables. Annette Obrestad was known for her big dark glasses at the table and her even bigger play.

She launched herself on to the poker world as a 15-year-old playing online and her rise was meteoric. In her first year playing professionally, she won around $1m online and took the largest single payout for a woman poker player, $2.01m, when she won the WSOP bracelet in London, and she hadn’t reached the age of 19. She may be the richest female gambler in the world, but she still holds two impressive titles: youngest WSOP bracelet winner and landing the largest single payout for a woman poker player. She is now resident in Vegas and has been legally allowed to play the tables for the past ten years. Photo by James Walsh