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The Top 20 Gambling Books of All Time 

by Scott Kacsmar
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Gambling books have been in print for many decades. With so many topics to write about from card counting to sports betting strategies to stories about high-stakes poker games, writers have a lot of freedom to cover these topics in ways that are engaging or informative to hungry readers who are seeking entertainment or a winning edge.

In choosing the top 20 gambling books of all time, we wanted to come up with a diverse group of books. You will find books that are heavy on strategy in case you are looking to sharpen your skills when playing at one of our recommended offshore sportsbooks. Others are focused on a good narrative and some are non-fiction stories involving the horror of true crimes.

20 Then One Year…: History’s Craziest Year as Seen by a Las Vegas Bookmaker

  • Author: Chris Andrews

Chris Andrews, a Las Vegas bookmaker, started keeping a journal in 2020 of his daily adventures from behind the counter. Little did he know that COVID-19 would turn the year into the craziest yet for sports bettors. In pulling back the curtain on how bookmakers operated during the pandemic, Andrews provides an interesting look at a year he’ll never forget in both his professional and personal life.

19 The Logic of Sports Betting

  • Author: Ed Miller/Matthew Davidow

Released in 2019 just a year after PASPA was overturned by the Supreme Court, Ed Miller brings his gambling expertise to sports betting to give a new age of online bettors the knowledge they need to know before they start making bets. Learn how lines are set by the sportsbooks and which strategies you need to adopt if you want to win over the long term with sports betting.

18 Blackjack for Blood

  • Author: Bryce Carlson

For blackjack fans, fewer books are a better read or resource than Bryce Carlson’s Blackjack for Blood. He dives deep into card counting techniques, showing his expertise in the area and still providing an easy-to-read explanation for novices hoping to test these strategies out themselves. The book also contains amusing, personal stories from Carlson’s experiences that make it a more enjoyable read beyond just grinding away on blackjack strategies and card counting.

17 American Roulette: How I Turned the Odds Upside Down

  • Author: Richard Marcus

This 2004 book by Richard Marcus is an amusing account of how he and several other skilled cheaters were able to swindle casinos around the globe out of their money. He travels everywhere from Las Vegas to London to Monte Carlo in an effort to win large sums of money from unsuspecting casinos. What was his secret? He used sleight of hand magic tricks on the gaming chips. You are reading a book by a con man here, so remember that when you take his word for everything being true, but it is an entertaining read.

16 The Man with the $100,000 Breasts and Other Gambling Stories

  • Author: Michael Konik

Just on title alone, this book from 1999 grabs your attention. Gambling expert Michael Konik tells several amusing stories about what he’s observed from gamblers, including the infamous story of Brian Zembic, the man who would do anything to win a bet. Someone bet Zembic that he wouldn’t get breast implants and keep them for a year for $100,000. Zembic took the bet, won the $100,000, and after growing so used to the breasts, he kept them too. Also included are stories about the person who determined the point spreads for Super Bowls and the gambler who turned $10,000 into $17 million with a pair of dice.

15 The Theory of Poker

  • Author: David Sklansky

A classic poker book, David Sklansky spent decades writing this one before it was first released in 1978. An author of 13 poker books, Sklansky goes over the fundamentals of poker strategy, game theory, and it continues to be relevant decades after its initial release.

14 Positively Fifth Street: Murderers, Cheetahs, and Binion’s World Series of Poker

  • Author: James McManus

In 2000, writer James McManus was sent by Harper’s magazine to do an objective story about the World Series of Poker. He instead ended up using his advance to enter the tournament himself, came close to winning it, and encounters a murder plot involving the victim’s girlfriend/ex-stripper and her ex-linebacker boyfriend. A wild, true story that mixes poker and murder, McManus came away with a story no one could have imagined would happen from his trip to Vegas. But what happens in Vegas is written amusingly in this personal memoir.

13 Soccernomics

  • Author: Simon Kuper

Soccer is the most popular sport in the world, and this is one of the best books discussing it from a betting and economics standpoint. First published in 2018, Soccernomics has become a brand for author Simon Kuper as he explains his analysis of the World Cup to design a betting plan that would allow him to win long term. A must-read for soccer fans, Kuper also provides fresh perspectives on how to analyze sports and come up with a winning strategy by looking at certain variables.

12 The Biggest Bluff

  • Author: Maria Konnikova

A newer release (2020), The Biggest Bluff shows Maria Konnikova’s transformation from a complete poker novice who never played a hand into a winner and player at the World Series of Poker. How did she do it? She hired a poker expert (Erik Seidel) to be her mentor, and as a psychologist, she learned how to read opponents and come to learn many things about herself in this interesting look at gambling from a psychological perspective.

11 Beat the Dealer

  • Author: Edward O. Thorp

Edward O. Thorp is a legend to gamblers, and he is still with us today at 91 years old. The former mathematics professor and hedge fund manager first published this groundbreaking work in 1962, and it essentially brought card counting in blackjack to the general public after he proved it can beat the house’s advantage. Thorp’s work was so groundbreaking that it forced casinos to adjust their games to make card counting more difficult. It is never a bad idea to read a classic from one of the legends in probability theory.

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

  • Author: Mark Paul

If the title alone doesn’t grab you, then the “Seabiscuit meets Narcos” comparison should do the trick. This is Mark Paul’s non-fiction book about a true story involving gambling on horse racing with true crime. Three unique gamblers come together at the 1988 Kentucky Derby, and there is a story involving the Mexican Cartel for some added intrigue. This is a well-written story with three diverse gamblers’ paths intersecting at the most famous horse race in the world. It’s an engaging, quick read and a fun alternative to the rest of our list.

9 Burning the Tables in Las Vegas

  • Author: Ian Andersen

There have been many books about blackjack over the years, but this release from expert Ian Andersen in 1999 still stands out as one of the best. Not only does Andersen share his expertise to give you winning strategies for blackjack and card counting, but he has a writing style that is humorous, engaging, and encourages readers with positivity that they can achieve what he has with the right amount of effort.

8 Titanic Thompson: The Man Who Bet on Everything

  • Author: Kevin Cook

Alvin Thompson (1892-1974) was one of the 20th century’s most infamous gamblers and hustlers. Some called him “Titanic” due to his claim he saw the Titanic sink. Kevin Cook’s biography is a wild tale of a real gambler who often traveled with golf clubs, a .45 revolver, and a suitcase filled with cash. He also claimed to have some Forrest Gump-like encounters with famous figures from his time as he hustled his way through life.

7 Bringing Down the House

  • Author: Ben Mezrich

This 2003 book is based on true stories about the MIT students who formed a blackjack team and infamously learned how to count cards to profit off Las Vegas casinos. Some of the stories and characters in the book have been exaggerated, but there have been film adaptations of this story in 21 (starring Kevin Spacey) and The Last Casino.

6 The Gambler

  • Author: Fyodor Dostoevsky

We said our list would be diverse, so here is a short novel from the legendary Russian writer Fyodor Dostoevsky about a young gambler and how his addiction affects his life. Fittingly enough, Dostoevsky wrote this in 1866 to pay off his own gambling debts as roulette was his game of choice. Maybe the shorter length compared to his usual writings is a good sign that this was rushed out to pay off a debt, but the quality is still there as this is considered another classic in Russian literature from the mind behind Crime and Punishment.

5 Gambler: Secrets from a Life at Risk

  • Author: Billy Walters

A new release (2023), Billy Walters has been called the Michael Jordan of sports gambling. Starting when he was 9 years old, Walters has always had an eye for success in sports betting, and here he shares dozens of pages on some of his secrets with us. He also opens up about his fractured relationship with golfer Phil Mickelson, who was reportedly worried about what the release of this memoir would do to his reputation as he is known to be a huge gambler (with huge losses, allegedly). Walters is a fascinating character in gambling and his book is a must read for sports bettors.

4 The Professor, the Banker, and the Suicide King

  • Author: Michael Craig

We know from Molly’s Game that high-stakes poker games among the rich do happen often behind closed doors. This 2005 book by Michael Craig takes a deep dive into some of the highest of high-stake games ever played in Las Vegas between characters referred to as the Professor (Howard Lederer), the Banker (Andrew Beal), and the Suicide King (Ted Forrest). These professional poker players were in a group known as The Corporation, and these poker games went on for years. Beal eventually lost $16 million in 2 days to a player in The Corporation.

3 Scarne’s Complete Guide to Gambling

  • Author: John Scarne

John Scarne (1903-1985) was a legend in the gambling field. A master magician and card manipulator, Scarne wrote several books about gambling in his career that are among the most classic in the genre. First released in 1961, his Complete Guide to Gambling is an essential read for those who want to learn strategies and secrets to being more successful at games of both chance and skill.

2 A Man for All Markets

  • Author: Edward O. Thorp

We already covered Edward O. Thorp earlier for Beat the Dealer. But if you wanted to know more about the man, this autobiography is a great look at his career, his contributions to the fields of gambling, mathematics, and finance, and some insight into how he became so successful in life. From Vegas to Wall Street, Thorp’s had a massive impact on gambling and is a true icon in the field.

1 Roll the Bones: The History of Gambling

  • Author: David G. Schwartz

Gambling historian David G. Schwartz knows his stuff in this comprehensive, meticulous look at gambling throughout the centuries. Schwartz takes the reader on a trip from gambling in ancient civilizations up until the 21st century and modern gambling forms. He does a great job of giving a global history of gambling, and he connects why humans love gambling so much. Not a book that’s heavy on strategy but a great read for anyone who appreciates detailed research and history.

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Scott Kacsmar
NFL football picks are Scott Kacsmar's expertise, serving as his main focus. He has contributed to various sports websites and blogs, such as NBC Sports, ESPN Insider, FiveThirtyEight, and, JoeWager. Originating from Pittsburgh, Scott maintains a love-hate connection with the Pirates.

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