10 most legendary sports gambling figures of all-time

Gambling is one of the oldest pursuits in the history of man. Pairs of loaded dice have been discovered in the ruins of Pompeii. There are cave drawings depicting gambling. Betting on sports, playing poker or counting cards in blackjack have produced legendary movies like Casino, Rounders and 21.

The United States Supreme Court then made a monumental decision in May 2018 to overturn PASPA, effectively granting to individual states the right to decide whether to allow legal sports betting. We are now entering the golden age of wagering on sports in the United States.

Often, though, our first dreams of making millions betting on sports come by hearing the stories of outlandish characters. Sometimes they’re super successful, sometimes they’re infamous for betting on sports and sometimes they’re both. Here are our 10 favorite sports betting figures in modern history, along with their incredible, legendary stories.

10. The Black Sox

Despite comparing themselves to slaves and other ridiculous complaints, professional athletes have it good in 2019. Superstars have real chances to build net worths of $100 million through lucrative contracts with their teams, endorsement deals, investment opportunities and personal brands.

In the 1910s, though, ballplayers enjoyed no such luxuries. Any player who refused to accept the terms of a contract from the team that controlled his rights was essentially banned from baseball. Chicago White Sox owner Charles Comiskey was notoriously cheap and developed a reputation for underpaying his players.

So in 1919, with the White Sox set to play the Cincinnati Reds in the World Series, a gambling syndicate was able to convince a number of the players to throw the series in exchange for money. Many associate the “Black Sox” scandal with Shoeless Joe Jackson, the most recognizable name on the team. But he did not attend the meeting that brokered the deal, and it’s unclear if he was involved.

The clubhouse was unofficially divided into a group of more straight-laced players and others willing to break rules. One of the straight-laced players, Red Faber, got the flu and could not pitch in the World Series. Two of the players “on the take” were pitchers and replaced Faber, including Lefty Williams, who went 0-3 as a starting pitcher in that World Series. The ruse got exposed pretty fast, leading to one of the largest gambling scandals in professional sports history.

9. Stuart “Stuey The Kid” Ungar

Before Chris Moneymaker started the poker boom of the 2000s, and before players like Phil Ivey, Phil Hellmuth and Daniel Negreanu became national legends, poker was much more of a niche sport. That’s when a man named Stuart Ungar built one of the most captivating, untold gambling stories ever told.

A brilliant 2005 New York Times article described him as a drug addict, degenerate, thrill-seeker, incredible tipper, womanizer, “pure id,” and “the swashbuckling enfant terrible of poker.” Though gin was his best game, he won back-to-back World Series of Poker main events by age 27. At one point, he won 10 of the 30 major poker events he entered, an unfathomable mark.

The man never opened a bank account, got his groceries at 7-Eleven and won and lost $30 million. He was the youngest WSOP champion in history in 1980, leading to his “The Kid” nickname. On Day 3 of the 1990 WSOP main event, Ungar went missing. Someone found him in his hotel room, unconscious from a drug overdose. He’d built such a chip lead that he made the final table even though he didn’t play another hand, blinding off the rest of his chips.

A broke, drug-riddled Ungar got staked in 1997. He almost passed out at the table on Day 1, but won a record third WSOP main event. He won $1 million, which he blew through in four months. He died in a cheap Las Vegas motel in 1998 with $800 in cash to his name, at 45 years old. He was the best winning poker player I ever saw, and he was one of the worst losing poker players I ever saw,” poker legend Doyle Brunson told the New York Times.

8. Michael Vick and dogfighting

Arguably the best rushing quarterback in NFL history, Michael Vick holds the all-time record for rushing yards by a quarterback in a season (1,039) and a career (6,109). He averaged a remarkable 7.0 yards per carry in his career. The four-time Pro Bowler was super popular with the Atlanta Falcons until 2007, when federal authorities uncovered a dog-fighting ring that Vick financed called “Bad Newz Kennels.”

Vick participated directly in the dog fights, collected some of the proceeds from bettors, and even was involved in killing numerous dogs that did not perform well in the fights. On the verge of financial ruin, having served time in federal prison, Vick eventually returned to the NFL with the Philadelphia Eagles in 2009, having missed two seasons in the prime of his career. He played his last NFL game in 2015.

7. Charles Barkley

“Sir Charles” has been one of the most personable, interesting and successful athletes turned broadcasters in sports. He’s also a legendary gambler. According to Barkley himself, he twice lost $2.5 million gambling in a period of six hours. He also claims to have won $700,000 one weekend betting on the Super Bowl and playing blackjack.

It’s unclear whether he bets on the NBA, as his contract with TNT probably disallows it. But he sure does make a lot of bold proclamations on air, both during the NCAA Tournament and during the NBA playoffs. It would not be surprising if Barkley was regularly betting on those opinions.

At one point, Barkley gambled a lot on the golf course, but developed an unusual hitch in his swing that he never was able to shed. Barkley has taken a break from betting on sports and cards, but said he doesn’t need to quit because he can “afford to gamble.”

6. Gilbert Arenas and the gun incident

Gilbert Arenas, or “Agent Zero,” became one of the best scorers in the NBA with the Washington Wizards, averaging 29.3 points per game in the 2005-06 season. A three-time NBA All-Star with more than 11,000 career points, Arenas also was a prolific card player and gambler, especially on a card game called booray.

On one team flight with the Wizards, he got involved in an intense booray game, trash-talking a player named Javaris Crittenton, who was on a big losing streak. The madder Crittenton got, the more Arenas berated him. Eventually, Crittenton made an off-color, aggressive remark, trying to act tough. To which Arenas replied that he’d burn Crittenton’s car while he was inside. Crittenton said he’d just shoot Arenas, and Arenas said he’d bring Crittenton the guns.

Days later, Arenas brought four unloaded guns in the locker room and told Crittenton to pick the one he wanted to get shot by. “You don’t need to shoot me with one of those,” Crittenton said, pulling out a loaded gun and pointing it at Arenas. “I’ve got one right here.” A Wild West shootout had broken out right in an NBA locker room due to betting on cards. Both players were out of the league in short order, and eventually, Crittenton killed someone in a drive-by shooting and is now in prison.

“I will bet you on anything,” Arenas told The Action Network in 2018. “Who’s gonna make the most half-court shots? A hundred grand, five shots. … As a competitor, you don’t back down. You can’t tell me that I can score 60 against Kobe and then I’m supposed to back down from a shooting challenge against DeShawn Stevenson? “You know what, I will beat you with one hand, bro, 20 G’s, put it up. Whoever’s on his side, bet 20K, too. I’m taking all bets.”

5. Michael Jordan and the conspiracy theory

The NBA long has been a magnet for conspiracy theories, like whether the league ever rigged its draft lottery. But the one that has received the most traction over the years has to do with Michael Jordan, arguably the greatest basketball player ever. One of the most notorious competitors of all-time, Jordan was known to gamble on just about anything – cards, golf, pickup basketball, and whatever else he could use as a forum to compete against you.

He got spotted in an Atlantic City casino one day before an Eastern Conference Finals game. One Jordan associate claimed publicly that “His Airness” owed him $1.25 million in golf-related wagers. Jordan retired from basketball in 1993, at 30 years old. He played minor league baseball for the Double-A Birmingham Barons of the Chicago White Sox minor-league system until the MLB strike in 1994, at which time he went back to the NBA.

But some think that then-commissioner David Stern quietly suspended Jordan due to his gambling and the negative publicity it drew, but kept the matter a secret. Interestingly, Jordan now owns the Charlotte Bobcats, and is part of a league in the NBA that is lobbying heavily to get a portion of revenues generated by legalized sports betting in the United States.

4. Amarillo Slim

4. AMARILLO SLIM

Born Thomas Preston Jr., “Amarillo Slim” was a hustler before that term made its way into our common lexicon. Before the World Series of Poker materialized 50 years ago, he toured the country as a rounder, looking for gambling action. He won the WSOP main event in 1972, and became one of poker’s early evangelizers in popular media.

However, Slim made his biggest name by winning a series of ridiculous high-stakes props. He beat a horse in a 100-yard dash because it wasn’t in a straight line. He beat American tennis pro Bobby Riggs in ping-pong because he got to choose the paddles (he picked frying pans and practiced ahead of time). Prop bets and betting on sports always has been a popular past-time for poker players, and Slim popularized that notion with his legendary side action.

3. Pete Rose

Pete Rose was one of the greatest hitters in MLB history. He holds the all-time record with 4,256 career hits. He won three World Series and made 17 All-Star teams. He eventually became player-manager of the Cincinnati Reds, the team with which he spent most of his career.

To this day, though, Pete Rose is not a member of the Hall of Fame. That’s because he got caught betting on baseball, often on the games he played or managed. For a long time he denied the allegations, and has been “banned” from baseball since the Dowd Report, which investigated his behavior. According to the report, Rose wagered on 52 games in 1987, risking thousands of dollars per day through a series of runners and bookies.

Because Rose is such an important figure in MLB history, which is a sport that thrives on historical numbers and records, his involvement in sports betting, especially on games in which he managed, was unique. Due to the decades of coverage it has generated, Rose’s betting on baseball probably is the most well-known scandal in the history of sports betting.

2. Phil Ivey

Phil Ivey earned the moniker “the Michael Jordan of poker,” with obvious parallels that go beyond race. First, just like Jordan, he struggled early in his sport of choice. He played poker with a fake id as a teenager, sometimes spending the night on the streets because he had no money to pay for a return bus trip from the casino.

Showing an innate and fine-tuned ability to read his opponents, Ivey at one point got recognized as the world’s best all-around poker player. He won three different bracelets at the 2002 WSOP, just two years after becoming the first player ever to defeat Amarillo Slim heads-up at a WSOP final table. In one eight-year period, he finished among the last 25 players at the WSOP main event four different times, an astounding accomplishment. He’s tied for second all-time with 10 WSOP bracelets, despite several prolonged absences from poker’s most visible event.

That’s in part due to what happened away from the felt. Part of Full Tilt Poker, Ivey drew blame and outrage when Black Friday took place. (The United States government seized Full Tilt’s domain, along with several other online poker sites. But Full Tilt had played fast and loose with people’s money, and could not pay out cash for its member’s accounts until years later, in many cases.)

According to HighStakesDB.com, Ivey had won $18.7 million on Full Tilt from 2007-10. Although it’s unclear whether Ivey had anything to do with Full Tilt’s troubles, he did not feel comfortable playing in the WSOP immediately after the scandal, and was involved in some legal battles.

He eventually turned to big cash games in Asia and then baccarat, where he and a partner used a technique called edge sorting to take millions of dollars from casinos all over the world. They got greedy one weekend, taking $11 million from a London casino in August 2012, leading to years-long litigation that eventually involved other casinos.

In May 2019, he released a MasterClass teaching poker strategy, and he played a few events in the 2018 WSOP. Otherwise, he’s been far from the public eye for years. Still, at the peak of the United States poker boom, Ivey probably was the No. 1 player in the world. Between his live tournament cashes, his online profits, his Asian cash games and his baccarat excursion, he’s won exponentially more money than the best poker players of the 1970s, 1980s and 1990s combined.

1. Billy Walters

In 2019, betting on sports often means machine learning, player profiling, algorithms and code. But in the 1980s, such things didn’t exist, at least not publicly. Walters was a member of the Computer Group that formed then, a machine that took into account dozens of factors and spat out a true line on games that the group used to exploit oddsmakers.

Walters had one losing season in 39 years, and could make as much as $60 million on a good year. That’s extremely unique, as sportsbooks often ban or limit winning players. Walters was one of the winningest players of all-time, but also built an underground network of runners, false herrings and other sophisticated systems that may never be matched.

He won $3.5 million betting on Super Bowl XLIV, and another $2.2 million on a USC-Michigan game in 2007, two of his largest single-game wins. He also exploited a roulette flaw in 1986 and won $3.8 million in one weekend – huge dollars for more than 30 years ago. In 2014, he had a net worth of more than $100 million, with a private jet, at least seven houses and many other large investments and business interests. He’s considered the most successful sports bettor of all-time.

The federal government tried (and failed) to convict him on sports gambling charges for years. But he did get arrested and jailed for insider trading in the stock market in a 2017 trial that also involved PGA Tour star Phil Mickelson.

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