Celebrities That Have Lost Big in Blackjack

Paris Hilton, Rapper Yo Gotti, Ben Affleck, Casino Poker Cards
Blackjack attracts more celebrities than any other casino game outside of poker. Like many gamblers, celebrities appreciate the combination of skill and luck involved with casino blackjack gaming.

However, fame and fortune doesn’t guarantee success on the blackjack tables. In fact, some celebrities have lost big playing this game.

Others haven’t necessarily lost money. But they’ve embarrassed themselves in other ways and been banned from casinos.

That said, I’ll discuss 7 celebrity blackjack players who have experienced the lowest of the lows with this game.

1 – Yo Gotti Loses $500,000 – Jay-Z Can’t Believe It

Yo Gotti has had a very successful rap career that includes hits such as The Art of Hustle, I Am, and White Friday. Unfortunately, he hasn’t proven a hit on the blackjack tables.

The 38-year-old was filmed playing a high-stakes blackjack session at Jay-Z’s Shawn Carter Charity Gala.

At one point, Yo Gotti put $500,000 on the table. This is one of the largest blackjack bets ever recorded.

It didn’t go so well for Yo Gotti either. He busted out and lost his massive wager.

Jay-Z was standing right next to Yo Gotti when the blow was delivered. Jazy-Z walked away and exclaimed “Oh my goodness” in disbelief over the result.

2 – Paris Hilton Loses a $175k Bentley – Gets Banned from Family Casino

Paris Hilton has won serious money in the past with blackjack. In 2014, she collected $50,000 in winnings after a DJ gig in Atlantic City.

However, the famed socialite has experienced more struggles than success with the game. Case in point: she once bet and lost a $175,000 Bentley at her family’s casino.

Richard Hilton made arrangements to have his daughter banned from the Hilton Las Vegas (now Las Vegas Hotel & Casino) gambling floor afterward.

Paris Hilton with Red Banned Logo

This incident hasn’t marked Paris’ only ban. Her boyfriend accidentally dropped a bag of cocaine in front of police while speaking with them in front of the Wynn Las Vegas. Both subsequently received bans from the Wynn.

3 – Charles Barkley Loses Millions in Blackjack

Charles Barkley was one of the greatest basketball players of his generation. During a career spanning from 1984 to 2000, he won the MVP award in 1993 and was an 11-time All-Star.

However, the Hall-of-Famer’s basketball skills haven’t translated to the blackjack felt. “Sir Charles” has lost a self-estimated $10 million through blackjack and sports betting.

Barkley once displayed his lack of blackjack strategy knowledge for TMZ.

Considering that he doesn’t know to hit on 16 when the dealer has 10, it’s no wonder why he’s lost so much.

The TNT analyst’s gambling problem broke in 2008. The Wynn sued him for an unpaid $400,000 marker. Barkley admitted that he had a gambling problem at this point.

Sir Charles had a unique strategy of trying to “win a million dollars” every time he visited Las Vegas. He eventually learned that chasing $1 million every session is a terrible goal.

Barkley continues playing blackjack and other forms of gambling. However, he’s more sensible about how much he risks these days.

4 – Ben Affleck Gets Banned for Card Counting

Unlike the other people on this list, Ben Affleck isn’t a blackjack loser from a financial perspective. Instead, he’s been banned from casinos and had his name dragged through the mud.

Affleck’s blackjack tale started in 2014. He received a ban from the Hard Rock Las Vegas for counting cards.

Ben Affleck, Poker Cards Spread Out

“I took some time to learn the game and became a decent blackjack player,” he said at the time. “And once I became decent, the casinos asked me not to play blackjack.

“I mean, the fact that being good at the game is against the rules at the casinos should tell you something about casinos.”

Affleck became a hero among gamblers for counting cards and beating Vegas. But his wife at the time, Jennifer Garner, wasn’t so pleased about the matter.

She became fed up with Affleck’s gambling and drinking shortly after the card-counting ban. The two have since divorced.

5 – Gladys Knight Drops $6 Million in Blackjack

Gladys Knight is one of the biggest R&B legends of all time. She’s sang hits like License To Kill, That’s What Friends Are For, and When a Child Is Born.

Away from the big stage, though, Knight always suffered from a blackjack addiction. She would lose up to $40,000 per night on the tables and has dropped an estimated $6 million overall.

Knight sometimes stayed up all night to play the game. However, she finally suffered a breaking point and quit playing.

Knight failed to take her kid to school in the morning, because she’d been playing blackjack and drinking all night long. This incident convinced her to walk away from the game and her mounting losses.

6 – Kerry Packer

Kerry Packer (1937 – 2005) was a billionaire Australian media tycoon. His net worth was estimated at AUD6.5 billion shortly before his passing.

Packer was one of the biggest high-stakes gamblers in history. He made six-figure wagers had enough wealth to back up his big gambles too.

The Aussie placed bets as large as AUD300,000 per hand. He also routinely won and lost millions of dollars during his gambling trips.

Aside from his extraordinarily large blackjack bets, Packer is the subject of many legendary gambling tales.

Kerry Packer with Pile of Money with Red X

He lost AUD28 million during a three-week gambling trip in Britain. This short-term loss is believed to be the largest in British history.

However, Packer won AUD33 million at the MGM Grand in Las Vegas. He also laid claim to several multimillion-dollar wins during holidays in the UK.

Packer was once spotted playing high-stakes roulette in South East England on four tables simultaneously. He had a £15 million bankroll in play during the session.

The most-famous story involving Packer is the time he offered to flip a coin for a Texas oilman’s $60 million fortune.

He’d grown tired of hearing the Texan brag about his wealth at the poker table. Packer shut the man up by saying, “I’ll flip you for it.”

7 – Terrance Watanabe

Terrance Watanabe earned a fortune as CEO of Oriental Trading Co. The Nebraskan sold his controlling stake in the company and retired with a fortune.

Thus began his lengthy gambling odyssey in Las Vegas. According to ABC News, Watanabe would sometimes gamble 24 hours per day.

He’d play three hands of blackjack simultaneously at $50,000 apiece. This heavy playing volume caused him to lose as much as $5 million per day.

Caesars Palace raked in nearly $127 million of Watanabe’s losses.

The latter claimed that Caesars Palace gave him generous amounts of alcohol and prescription pills to keep him gambling.

Watanabe eventually failed to repay $14 million worth of losses to Caesars. The Casino sued him for the amount, and both sides settled out of court.


Celebrities might achieve major success in the entertainment and/or business world. However, their fame doesn’t make them any less immune to the blackjack house edge.

Yo Gotti became the most-recent person to find this out. He lost a $500,000 bet in a single hand during Jay-Z’s charity event.

Paris Hilton is another celeb who lost big. She wagered and lost a $175,000 family owned Bentley. Her father subsequently got her banned from the casino’s gambling tables.

Ben Affleck is another blackjack player who drew a ban. But unlike Hilton, his ban came from being too successful as a card counter. Unfortunately for Affleck, he eventually lost his marriage as a result of gambling.

Charles Barkley has proved publicly in front of TMZ that he’s not the most-knowledgeable blackjack player. However, this limited knowledge hasn’t stopped him from losing millions of dollars on the game.

Gladys Knight developed such a bad blackjack habit that she once forgot to take her son to school. She quit afterward but not before losing $6 million lifetime.

Kerry Packer and Terrance Watanabe are two successful businessmen who frequented the blackjack tables. Only the late billionaire Packer, though, could afford to bet and lose big.

Watanabe, in contrast, blew too much money on blackjack and other games. The former Oriental Trading Co. owner lost most of his fortune in casinos.

Blackjack is quite an alluring game. That said, we’ll eventually see other celebrities join this list of the biggest gambling losers.