Chips, Fame, and Fortune: Inside Hollywood’s Wildest Gambling Adventures

Glitz maybe Las Vegas’ defining characteristic, but fortunes are won as readily as they are lost under that city’s impressively lit canopy, and celebrity gambling adventures have become nearly as much a part of popular culture as the place itself. With high stakes, these stories featuring A-list actors and iconic sports figures turn the heart-pounding highs of high-stakes gambling into legendary status, breeding fascination and warnings. These larger-than-life characters are those tales that not only glamorize such an enthralling casino world but also cast a shadow of the darker side of the same; that same charisma that draws them to the tables is not always guarding them away from the chaos. These celebrities gamble out on these glitzy and perilous paths, and the trademarks they leave reflect the complexities of their personalities and how they gamble.

Michael Jordan

Michael Jordan, perhaps the greatest basketball player ever, is celebrated for his competitive nature off the court, especially for high-stakes gambling. He has been fascinated and critiqued for his passion for games like poker and blackjack — and his propensity to place huge golf bets. Probably the most talked about incident takes place in 1993 when Jordan was seen gambling in Atlantic City while winning the Eastern Conference Finals, raising the question of his gambling affecting his gameplay. However, his high-stakes lifestyle was further strained that same year when he admitted to losing $1.25 million on a golf bet with businessman Richard Esquinas. But Jordan says his gambling never interfered with his professional career, and his unquenchable competitive spirit drives his desire to lift the stakes on the court or when playing poker.

Charlie Sheen

Charlie Sheen’s life has been a flurry of headline drama at every turn, and his gambling stories dovetail in as expected. Sheen is famous for his appreciation of blackjack and sports betting, and his most outlandish stories seem like they could have sprung from a movie script. He famously lost $200,000 in one blackjack session at the Palms Casino Resort in Las Vegas 2006. But it was just a prelude to a more horrific $165,000 blowup at the tables in five years’ time. To Sheen, gambling was an escape (and it could be awful) when combined with his infamous battles with substance abuse, a destructive cycle. Yet he admitted his gambling addiction as nothing more than one aspect of his self-destructive tendencies, yet he could never truly break the pull of the game. Hollywood folklore has been made of his legendary high-stakes poker games against celebrity rivals such as Ben Affleck and Tobey Maguire.

Allen Iverson

Celebrated for the electrifying play on the court, basketball legend Allen Iverson’s personal life was very different, as well as a series of gambling and alcohol problems that also resulted in his financial ruin. Despite making a $200 million fortune from his NBA career, Iverson squandered his wealth through a high-risk lifestyle, playing countless hours in casinos. His behavior grew so bad that it got to the point where he was banned from establishments in Detroit and Atlantic City.

John Daly

John Daly’s potted history on the PGA Tour has been shaped as much by his enormous gambling losses, which he freely admits add up to something in the region of $50m or $60m over 15 years, as by his colorful exploits. Compulsive gambling drained his finances and turned his once-promising golf career into shambles, leaving him having to put away the game once more. But eventually, that addiction to slot machines and blackjack brought Daly into financial turmoil.

Ben Affleck

We all know Ben Affleck’s love of blackjack, winning $800,000 in a single night in 2001, is a testament to his skill and ability to think strategically. Despite that, Affleck was banned from Las Vegas casino for using a rather sophisticated blackjack strategy — card counting — which is neither illegal nor illegal. Affleck is open about his battles with gambling and addiction and has gone to rehab more than once, just as a successful celebrity can be as prone to pitfalls as those less fortunate.

Robert De Niro

Acclaimed Italian American actor Robert De Niro, famous for playing Asso in Martin Scorsese’s “Casino,” has been so enamored with the cinematic love of gambling that he has carried that passion onto the real world. Inspired by the film, De Niro is also undertaking an effort to develop a luxury casino resort in the tropical paradise of Antigua and Barbuda. Part of this $250 million effort is a partnership with legendary businessman James Packer. De Niro has not been shy about heading to the gambling industry before; he’s already invested in the Nobu Hotel Manila, which includes a collection of luxury hotels and casinos that show 380 gaming tables and 1,700 slot machines.

Matt Damon and Edward Norton

Known for their roles in the movie “Rounders,” Matt Damon and Edward Norton have taken their on-screen passion for poker and made a mark in the poker community. While these aren’t the only actors who aren’t in it for the money (both have competed in high-stakes poker tournaments as well), they are enthusiasts of the game and devoted to the craft. It’s worth noting how well Matt Damon plays the game, as he just won at a World Series of Poker (WSOP) event and, together with that, definitively strengthened his reputation as a formidable player.

Michael Phelps

Michael Phelps has been winning just as much at the poker tables as at the pool. Phelps is a known fixture at poker tournaments and celebrity events for displaying his competitive spirit and never-letting-go attitude. This quality can be used beyond swimming. He may not have the time in the poker world that seasoned poker professionals, but these traits have allowed him to have enough to compete in the poker world, his remarkable adaptation, and the piety to succeed in whichever arena he may decide to enter.

Ray Romano

Comedians often play poker, and Ray Romano is known for being funny in funnyman terms and a decent gambler. Romano is known for comedy work on screen but has taken the sport of poker seriously by appearing in several World Series of Poker (WSOP) events and other professional poker tournaments. Poker fans will attest to how he blends the strategic and