There’s something liberating about experiencing an individual or group of people try to cheat the odds and walk away with millions, even if that doesn’t quite go to plan. 

That’s exactly what you’ll find in our list of incredible books about gambling, heart-stopping true stories with some of the most captivating sentences on the planet sandwiched between two covers. 

From the story of six MIT students taking Vegas for millions to the true tale of three gamblers, the Kentucky Derby, and the Mexican cartel. 

Here are 5 of the most incredible books about gambling that you could ever hope to read. 

1. Bringing Down The House: How Six Students Took Vegas for Millions

If you’re a lover of gambling movies as well as gambling literature, chances are that the title of this novel sounds somewhat familiar. 

Bringing Down The House: How Six Students Took Vegas for Millions, written by Ben Mezrich, was actually adapted to become a pair of movies in “The Last Casino” and more famously “21” starring Kevin Spacey. 

The non-fiction book follows Kevin Lewis, an MIT graduate invited to join the MIT Blackjack  Team in 1993 by two of the top players, Jason Fisher and Andre Martinez. Financed by Micky Rosa, a colorful character with an obsession with bringing down the house, the team planned to visit Vegas with at least one other team to play blackjack up and down the Las Vegas strip.

The book makes its way through the highs and lows of the fast-paced, adrenaline-fuelled lifestyle of a professional gambler in the incredible tale. However, ultimately, conflicts in personalities and prevention methods in card counting at the casinos eventually ended this gritty fairytale MIT Blackjack Team.

A must-read for any true blackjack fan.  

2. The Man With the $100,000 Breasts and Other Gambling Stories

Here’s a title that’ll grab attention from all walks of life and for good reason too, it’s completely true. 

Brian Zembic, a magician and high-stakes gambler specializing in both blackjack and backgammon got his 15 minutes of fame in 1996 when he was wagered to receive breast implants (and keep them for a year) to win $100,000. Zembic, although hesitant at first, took the bet and won although opted not to remove his breast implants for 20 years after becoming accustomed to them. 

That’s just one of the many tales to be found inside “The Man With the $100,000 Breasts and Other Gambling Stories” by Michael Konik. The book acts as a collection of the very best magazine pieces over the years from the renowned gambling writer’s career.

Readers will also find incredible stories of a hardcore dice shooter who borrowed $10,000 and turned it into $17 million and a marketing genius who created a “900” line for selecting winners of NFL games, having his four-year-old son make the picks. 

It’s a wealth of “did you know?” conversation starters and incredible, hilarious, and sometimes downright unbelievable stories from cover to cover.  

3. Super/System 

No list of gambling literature is complete with at least one strategy novel and we’re opting for the game-gaming “Super System” to occupy the point in our list. 

Written by the world-famous poker player Doyle “Texas Dolly” Brunson, Super/System was one of the very first books about the strategy of poker, released in 1979. However, to this day, poker players across the globe swear by Brunson’s book with Doyle himself suggesting that it probably cost him more money than he was paid for writing it due to its influence on the game. 

The strategy book covers everything one could wish to know about the game of poker and with help from some of the biggest players in the game at the time, gave an unprecedented insight into how professional players see the game. 

• Draw poker – written by Mike Caro, 
• Seven-card stud poker – written by Chip Reese
• Lowball poker – written by Joey Hawthorne and Doyle Brunson
• Seven-card stud poker high-low split (with no qualifier for low) – written by David Sklansky
• Limit Texas hold ’em – written by Bobby Baldwin 
• No-limit Texas hold ’em – written by Doyle Brunson

With information on tells as well as the strategy and numbers behind the probability of hands, there’s no better place to start when looking to get into the beautiful game of poker. 

4. Tony 10: The astonishing story of the postman who gambled €10,000,000… and lost it all

Tony 10, that was the online username of the betting account used by Tony O’Reilly, an unassuming postman who made frontpage news in 2011.

O’Reilly, a typical postman, stole an incredible €1.75 million from An Post while residing as the branch manager in Gorey, Co. Wexford. With the money, he funded his gambling addiction, a problem that started with a simple small bet of just €1 that rose to an incredible €10 million. 

Tony’s troubles with online gambling lead to the loss of his job, his family, his home, ultimately landing him a prison sentence for his crimes. Today, Tony O’Reilly is a fully qualified counselor and social activist focusing on raising awareness of gambling addiction, using his past experiences for good. 

‘There is more drama in Chapter 10 of this book alone than you’d find in an entire year’s subscription to Netflix.’ – Brian Boyd

Tony now dedicates his time to helping young men avoid the impulses and pressures similar to those he faced himself in his incredible story. 

5. The Greatest Gambling Story Ever Told: A True Tale of Three Gamblers, The Kentucky Derby, and the Mexican Cartel

It’s Seabiscuit meets Narcos in one of the very best true-life gambling stories ever told.

“The Greatest Gambling Story Ever Told: A True Tale of Three Gamblers, The Kentucky Derby, and the Mexican Cartel” follows the true story of the gamblers that bet millions on the Kentucky Derby against the Mexican Cartel. If that’s a sentence that doesn’t get you excited, nothing will. 

The story of three fun-loving gamblers, Miami Paul, Dino Mateo, and Big Bernie who unknowingly place (and win) an incredible longshot bet on the three-year-old racehorse “Winning Colors” with members of a suspected drug cartel at a racetrack in Tijuana, Mexico.

The story follows the trio as they attempt to claim their prize, putting their lives on the line in a heart-pounding race across the U.S.-Mexico border.

A heart-stopping tale loved by anybody and everybody.