Gambling has been a popular form of entertainment around the world for hundreds of years now, so it only makes sense some of the best writers and novelists of the era have tackled the subject. From big winners to big losers, from casinos to bets between friends, the subject provides fertile ground for narrative excitement and philosophical debate. In fact, there are too many to fit on this list. Sorry if your favorite missed out. But which ones did make the cut?
From classic 19th century Russian literature to a dramatization of the true story behind the Mafia’s role in building Las Vegas, to a modern-day sports betting biography full of salacious revelations, there are five of the greatest books about gambling ever written.
The Bet by Anton Chekhov is a Philosophical Masterpiece
Part exploration of what it means to gamble, part philosophical treatise on the effects of isolation on human beings, Chekhov’s short story is a classic of 19th century literature. One that involves an insanely huge wager of two million roubles – which would be worth around $30 million to $40 million in today’s dollars.
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The basic plot sees a wealthy Russian banker debate the morality of capital punishment with a young lawyer – before offering to pay him the huge two million sum if he can survive 15 years of solitary confinement. Without giving anything away, the twist ending is is a shocker that might make you think about gambling – and lots of other things – in a different way.
Bonus Fact: Chekhov wrote the majority of this short story in just eight days, on a deadline for a commission from a St Petersburg-based newspaper.
Gambler: Secrets from a Life at Risk by Billy Walters
The much-anticipated memoir from possibly the greatest sports bettor of all time. In this tell-all autobiography Walters recounts how he became the most successful sports gambler ever over a thirty-six year winning streak.
Full of celebrity figures and famous names (some of which are featured again later in this article), this book is not just revealing it’s also part instructional. So if you’re an actual gambler interested in learning the lessons from one of the best, while being entertained with a good narrative to boot, this could be the book for you.
Walters, now estimated to be worth several hundred million dollars, details how he managed to bet at least a million dollars a week across various sports for the past three decades. However, the book doesn’t shy away from his periods of loss, addiction, obsession and tilt. Or, indeed, famous faces who risked losing it all. Making Walters’ well-written book both a success story and a cautionary tale.
Molly’s Game by Molly Bloom is the Premier Poker Memoir
Few kinds of gambling have had as much wide cultural impact as Texas Hold ‘Em poker. And few of the many books about the game have had as much success as Molly’s Game.
The real life memoir of socialite Molly Bloom, Molly’s Game chronicles here rise from Olympic skiing hopeful to being the front of house organizer for illegal high stakes poker games in Hollywood, Los Angeles. The nose-bleed stakes cash games attracted a crew of Hollywood stars and wealthy elites including Tobey Maguire, Leonardo Di Caprio, Matt Damon, Alec Gores and Andy Beal.
The game’s came tumbling down after raids from federal authorities between 2011 and 2013. Bloom was sentenced to 200 hours of community service and a fine of $125,000 for her role in the illegal gambling operation.
Molly’s Game ended up being adapted into a 2017 movie, the directorial debut of Aaron Sorkin, which is also considered one of the best poker movies of all time.
Casino: Love and Honor in Las Vegas by Nicholas Pileggi Also Became a Classic Movie
Long-time crime reporter Pillegi’s 1995 book is the quintessential Las Vegas crime expose, and it was also the basis for probably the most famous gambling movie of all time – Martin Scorsese’s Casino.
Casino covers the Chicago Mafia-influenced early days of modern Las Vegas in the 1970s and early 1980s, including now infamous names like Frank “Lefty” Rosenthal and
Anthony Spilotro. The book chronicles the rise and fall of the legendary Stardust Casino, as the Mob grapples with the intricacies of trying to run a semi-legitimate business while continuing their illegal activities and evading law enforcement.
While the details were embellished and names changed for the now-iconic movie, the original book remains an incredibly well researched but riveting true story account of Las Vegas’ criminal past. One that the modern day Sin City gambling mega corps would probably like to forget.
