Top 10 Greatest Athletes Of All Time… at Gambling

What do Michael Jordan, Pete Rose, and Floyd Mayweather Jr. all have in common? No, they’re not just three of the top 10 greatest athletes of all time. They’re three of the most notorious degenerate gamblers in the sporting world. Yes, these three gambled more than their money away.

The Top 10 Athlete Degens

1. Pete Rose

Of course, Rose has to be number one on this list or any list in terms of gambling. In his case, in particular, it’s sports betting. Who is Pete Rose? Most people know him as the “guy that’s banned from the MLB because he bet on his team.” But before he was known as a degenerate gambler, he was arguably the greatest baseball player.

Rose is still the MLB’s all-time leader in hits with 4,256. He won three World Series titles, three batting titles, an MVP, two Gold Gloves, and the Rookie of the Year Award. On top of that, he was named to 17 All-Star games from five positions (another MLB record).

Unfortunately, all of these are overshadowed by his gambling scandals. In August 1989, Rose was accused of having wagered on MLB games while he played for and managed the Cincinnati Reds. In June 2015, ESPN found Rose guilty of these accusations in its own independent investigation.

Rose initially denied these allegations and even sued the entities accusing him. However, it did not prevent the MLB from permanently barring him from the Hall of Fame and from attending or participating in the league for at least 25 years.

Ultimately, Rose admitted to betting on the games in his autobiography My Prison Without Bars, which was released on January 8, 2004. Rose also admitted on The Dan Patrick Show in 2007 that he “bet on his team every night” and that he “did everything in his power every night to win.”

And finally, on the eve of the 25th anniversary of his 4,192nd hit, Rose sincerely apologized to his teammates from the “Big Red Machine.”

Alas, while Rose is one of the top 10 greatest athletes of all time, he will always be associated with gambling.

2. Michael Jordan

Michael Jordan needs no introduction for most people. But for those living under a rock, the “GOAT” (greatest of all time) won six NBA titles, six Finals MVPs, five regular season MVPs, and was a 10-time scoring champion. More importantly, Jordan brought basketball to new heights and is the biggest reason why the sport is where it is now.

But “His Airness” was far from perfect, especially as a person. Outside of punching Steve Kerr during practice and cheating in the smallest games, Jordan was an avid gambler.

Michael Jordan’s stats on the court were eye-popping. But off the court, he lost plenty due to his compulsive gambling habits. He admitted to covering $57,000 in gambling losses while author Richard Esquinas also said he once won $1.25 million from Jordan while golfing.

Jordan would also be seen gambling in Atlantic City, New Jersey during the conference finals. In 2005, Jordan discussed his gambling with Ed Bradley on 60 Minutes. He said, “Yeah, I’ve gotten myself into situations where I would not walk away and I’ve pushed the envelope. Is that compulsive? Yeah, it depends on how you look at it. If you’re willing to jeopardize your livelihood and your family, then yeah.”

The NBA legend’s gambling was apparently so bad that then-commissioner David Stern suspended him in 1993, which was passed as a surprise “retirement.” Of course, this was debunked though fans continue to spread it as part of the MJ mythos.

3. Charles Barkley

From Jordan to one of his famous rivals: Charles Barkley. The pair shared many things in common. They were both fiercely competitive, loved playing golf, and had compulsive gambling habits. Like Jordan, Barkley gambled and lost plenty. He admitted in a 2007 interview with ESPN’s Trey Wingo that he had lost $10 million from gambling.

“It’s not a problem. If you’re a drug addict or an alcoholic, those are problems. I gamble far too much money. As long as I can continue to do it I don’t think it’s a problem,” Barkley once told fellow TNT broadcaster Ernie Johnson when approached by the topic. “Do I think it’s a bad habit? Yes, I think it’s a bad habit. Am I going to continue to do it? Yes, I’m going to continue to do it.”

In May 2008, the Wynn Las Vegas casino sued Barkley alleging he failed to pay a $400,000 debt stemming from October 2007. Barkley quickly went back on his words and said “I’ve go to stop gambling. I am not going to gamble anymore.”

But sorry, “Chuckster”. It’s hard to believe as his losses now are said to amount to over $20 million. He was a legendary basketball player, one who won everything but a championship. And as far as hitting the casinos, Barkley is among the 10 greatest athletes of all time at being a degenerate gambler.

4. Phil Mickelson

Speaking of gold, Phil Mickelson shares a gambling “habit” with his basketball counterparts. The World Golf Hall of Fame member has six PGA major championships and over $104 million in career winnings. He’s also authored many memorable stories on the golf course such as becoming the first 50-year-old to win a major in 2021.

But outside of his golf stories, Mickelson also has a long list of gambling “adventures.” You can write a book about it. Among these include a detailed report from the SEC that Mickelson lost over $40 million in a four-year stretch from 2010 to 2014. This was roughly equivalent to his estimated annual income in this period.

Some report that Mickelson’s financial woes, tied with his degenerate gambling habits, also contributed to his split with longtime caddie Jim “Bones” Mackay. After reports kept coming in on Mickelson’s issues, he had to take a break from the PGA Tour. He then opened up about his gambling to Sports Illustrated’s Bob Harig

“My gambling got to a point of being reckless and embarrassing,” he said. “I had to address it. And I’ve been addressing it for a number of years. And for hundreds of hours of therapy. I feel good where I’m at there. My family and I are and have been financially secure for some time.”

Now it’s become a bit clearer why Mickelson turned his back on the Tour and joined LIV Golf.

5. John Daly

Mickelson is not the only colorful character from golf. John Daly could rival “Lefty” in terms of his exploits both on and off the course. The 57-year-old rose to prominence in 1991 when he came from out of nowhere to win the 1991 PGA Championship followed by his playoff victory in the 1995 Open.

Daly reportedly has earned over $12 million playing golf and has opened several successful businesses. He even has written and recorded music with two albums already released. And like Mickelson, “Wild Thing” has a thing for gambling.

The Californian revealed in 2006 through his autobiography, My Life In and Out of the Rough: The Truth Behind All That Bull**** You Think You Know About Me that he had a gambling problem. Daly reportedly lost around $50 to $60 million over a 15-year period.

Daly even claims to have lost $1.5 million in October 2005 after winning half that amount at the WGC-American Express tournament. He would lose $5,000 on a slot machine and then play seven simultaneous hands of blackjack for $5,000 to $15,0000 each.

“I did it. I moved on from it,” Daly said in an interview with Yahoo’s In Depth With Graham Bensinger. “I had a lot of fun doing it. I love the action, I love the adrenaline going in there.”

But now the golf star says he’s toned down his wild gambling habits some. “Now if I gamble, I go in and play the $25 slots.”

6. Joe Namath

Few NFL stars have the same profile as Joe Namath, aptly named “Broadway Joe.” He took that moniker and made the most of it as his Super Bowl exploits and Hall of Fame career were the least interesting things about him. Yes, Mr. Namath was all things you expect from a “rockstar” of the 1970s and 1980s. He was a womanizer, a substance abuser, and a degenerate gambler.

While Namath’s tales of gambling are not as comprehensive as the others on this list, he does have one thing “over” them. Namath owned a nightclub called Bachelors III, which allegedly became a hangout for mobsters. He ultimately had to sell the club to continue playing in the NFL after his faux retirements stopped fooling the commissioner.

7. Floyd Mayweather Jr.

They don’t call Floyd Mayweather Jr. “Money” for no reason. Other than frequently commanding eight figures to duck punches over 12 rounds, Mayweather is a notorious sports bettor. And unlike others on this list, the unbeaten boxer publicly brags about his bets. Mayweather has won millions betting on the NFL and hundreds of thousands on both the NBA and UFC.

Of course, Mayweather also bets on himself in some of his fights and he always wins. But for obvious reasons, we don’t hear much about his losses. However, a Maxim report stated that Mayweather lost up to $50 million in 2017 alone. Mayweather has also told ESPN that he’s been making bets since he was a kid. So don’t expect “Money” to stop throwing money at the casinos.

8. Michael Vick

To this day, Michael Vick remains one of the NFL’s least popular players. And it’s for reasons off the field. While Vick was an exciting player who popularized the idea of a running quarterback, he made one too many poor decisions in his personal life. These involve his many links to gambling including one that got him sent to prison: dogfighting.

While Vick himself was not a degenerate gambler in the mold of the others here, the fact he was an organizer and promoter of these operations. He not only oversaw and actively engaged in the killing of the pit bulls, but also supplied the money for the gambling.

And as fast as Vick was on the field, these were charges that he couldn’t run away from.

9. Allen Iverson

The third NBA legend on this list is a diminutive star not unlike players like Lionel Messi’s stats, Iverson put up numbers that led to him winning a league MVP, 11 All-Star selections, and four scoring titles. But the 6’0” baller was a cultural icon both for his basketball prowess and scandalous personal life.

“A.I.” frequently butted heads with authority figures both in the NBA and in society. Among his more publicized issues are his alcoholism and gambling problems. Many surmised during the late 2000s that the NBA star would either “drink or gamble his life away.” Iverson accumulated plenty of gambling debt and even got banned from some casinos.

Now, the 48-year-old is not in the best of financial states despite being valued at over $200 million at the time of his retirement.

10. The 1919 Chicago “Black” Sox

Seventy years before Rose’s betting fiasco, an entire MLB team got implicated in its own game-fixing scandal. Eight players from the 1919 Chicago White Sox were accused of throwing the 1919 World Series against the Cincinnati Reds. A gambling syndicate led by Arnold Rothstein allegedly paid off several of the players.

Despite several of them being acquitted in a public trial, they were still permanently banned from professional baseball. “Shoeless” Joe Jackson, a star outfielder worthy of the Hall of Fame, was also banned from being enshrined here, which set a precedent that applied to the likes of Rose. To this day, this Chicago the “Black” Sox scandal remains an important part of sports lore for dark reasons.

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