In the 1992-1993 season, Charles Barkley was playing for the Houston Rockets at the age of 34. It was the only season in which he played more than 40 games in a season, and the end result was a career year. Barkley was named to the All-NBA First Team, and finished with over 25 points per game.

Charles Barkley once received an unprecedented $5,000 fine after making three in-game bets with Mark Jackson. Let that marinate for a minute. Here is an article that you will see referenced a lot in the future, and for good reason. It’s the story of Charles Barkley’s gambling addiction, and the fallout that he, Mark Jackson, and his gambling addiction caused. It’s an amazing story.

Charles Barkley once received an unprecedented $5,000 fine after making three bets in a single NBA game. The fine was imposed by the league itself, not by the game’s referees or officials. After the game, Barkley made three separate bets against the same team, the Los Angeles Clippers, each of which was in the form of a $5,000 wager. Each bet was made with the understanding that the winner would receive any $500 gains above the $5,000 low limit, and lose any $1,000 losses.

Anyone who has ever watched Inside the NBA on TNT can attest that Charles Barkley has no problem expressing his opinion. It may be interesting for television, but some things are better left unspoken. Sir Charles learned this from his own experience in January 1990.

During the game against the New York Knicks, Chuck decided to make some bets with Mark Jackson on the field. Barkley didn’t stop there though. He later spoke to the media about the bet, which resulted in an unprecedented fine for both men.

Charles Barkley has made a lot of money and has no problem with some

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During his successful playing career and second life as a television analyst, Barkley amassed an estimated fortune of $50 million. This money allowed Chuck to indulge in one of his favorite hobbies: gambling.

Over the years, some details have emerged about Barkley’s playing habits. For example, an Associated Press (h/t ESPN) article from 2007 mentions that the former attacker claimed to have won about $700,000 with blackjack and sports betting during a weekend in Las Vegas. The same article mentions that Sir Charles lost $2.5 million in six hours, but gives no further details.

This amount is just the tip of the iceberg. In the same AP article is a link to an interview Barkley did with ESPN in 2006. During that conversation, he estimated that he had lost about $10 million in gambling.

It’s a stupid, bad habit. I have a problem, Barkley said. But the problem is, if you can’t afford it. I can afford to play. I love gambling and I have no intention of giving it up.

For gambling, Sir Charles is fined $5,000

Charles Barkley carries the ball to the rim for the Philadelphia 76ers. | Focus on Sport/Getty Images

However, some of Barkley’s bets were not made at the casino. There are at least three balls known to be thrown during an NBA game.

As reported in a 1990 New York Times article, Barkley allegedly made two bets on Mark Jackson during a meeting with the New York Knicks. This was revealed after he mentioned the bets in the afterthought.

Barkley said he had bet Jackson $1,000 that he would hit two free throws with 22.4 seconds left. Barkley won that bet, according to the Times. Barkley then bet Jackson couldn’t tie the score with a 3-pointer. Barkley lost that bet.

Chuck also said he had lost a $500 bet with Jackson in last season’s playoffs, but that he has since made up for it and wants [his] money. However, Nix’s defender maintained that Barkley owed him an earlier amount, and since neither amount was recovered, the two were even.

But Commissioner David Stern was not interested in these details. Both players were fined $5,000 and called to the league office to explain the incident.

According to the Times article, the fines are the first ever imposed on N.B.A. players for such an offense.

Losing $5,000 Is Not Charles Barkley’s Biggest Money Loss

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While Barkley hasn’t cared too much about match losses in the past, it’s safe to assume he would have been upset if he opened his mouth to receive a $5,000 fine. Compared to his biggest financial mistake, however, this fine was a drop in the bucket.

As he admitted in 2019 during an appearance on Dr. Phil’s podcast, Sir Charles has struggled with a problem many professional athletes face. Once the money started flowing, the attacker was under pressure to share the wealth.

It’s probably the biggest mistake I’ve ever made in my life, Barkley said. You know, I probably have $4 million I gave to friends I don’t owe anything to. You know, you have all this money and you want your friends to like you. But just by giving money to people, you first become a facilitator. But it always ends up ruining your relationship, because if you give someone $500,000, they’ll hate you the first time you say no.

Even with these problems, Barkley wasn’t in too bad of shape. When you have millions of dollars in assets, it’s easy to make financial mistakes.

I need some help: In the United States, please contact the National Gaming Council hotline at 1-800-522-4700.

COMPARED TO: Charles Barkley’s NBA hazing included 12 sacks, hot milk and delivering newspapers Dr. J: You really pissed me off

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