10 Gambling Books You Need To Read
Rediscovering the stories behind poker’s Golden Era: My Top 10 books that chronicle the leadup and aftermath of the Poker Boom.
I recently mentioned that one of my favorite gambling books, Jon Bradshaw’s Fast Company, was discussed on journalist David Hill’s podcast, American Gambler:
As I mentioned in my post, most of the “best gambling books” columns I’ve written over the years are no longer online, so I’ve decided to redo some lists, starting with the books that capture the poker world before and during the early days of the Poker Boom.
As you can see from the picture below, I have a pretty extensive collection of gambling books (some date to the 1800s), and I have another 100 or so poker/gambling books packed up in boxes.
So here are my choices for anyone interested in the early internet era of online gambling, through the early days of the Poker Boom — I’ll put together a few more lists in the future: 10 Best Gambling History Books, 10 Best Gambling Biographies, 10 Most Fun Gambling Reads, and maybe even the 10 Best Gambling Movies.
This one will be free to all subscribers.
The Biggest Game in Town, by Al Alvarez
Alvarez’s chronicle of the 1981 World Series of Poker at Binion's Horseshoe Casino is as far back in time as I’ll go for this list, and I’m only including it because many of the main characters were part of the early Poker Boom. This was the first book to dive into the murky waters of professional poker, and somehow it captured the drama, eccentric personalities, and psychological allure of the high-stakes poker community in a way that has only been repeated once since (in my opinion).
Big Deal, by Anthony Holden
Another pre-pre-Poker Boom book, after flaming out in the 1988 World Series of Poker Main Event, British journalist Anthony Holden spent a year trying to make it as a professional poker player from 1988 to 1989, and Big Deal is his first-hand account. In a break from most gambling accounts, Holden shares the highs and the many lows, psychological insights, and encounters with legends like Doyle Brunson, Amarillo Slim, and Stu Ungar.
Positively Fifth Street, by James McManus
Positively Fifth Street is actually two books brilliantly intertwined by McManus, who arrived in Las Vegas on assignment for Harper's Magazine under the auspices of covering women playing in the 2000 World Series of Poker and Ted Binion's murder trial. The story arc of the WSOP takes an unexpected twist when McManus enters the Main Event and makes an improbable run to the final table. Just an all-around great book that transcends gambling.
All In: The (Almost) Entirely True Story of the World Series of Poker, by Jonathan Grotenstein and Storms Reback
All In traces the World Series of Poker from its 1970 origins as a gathering of Texas road gamblers at Binion's Horseshoe to a full-blown cultural phenomenon. The book recounts pivotal hands, brutal beats, and colorful characters like Doyle Brunson, Amarillo Slim, and Chris Moneymaker. Through interviews and archival research, they highlight poker's transformation from shady backrooms to mainstream acceptance, with a lot of never-before-seen anecdotes.
The Moneymaker Effect, by Eric Raskin
Raskin’s oral history of the 2003 World Series of Poker, where amateur Chris Moneymaker's improbable victory ignited the Poker Boom. Raskin’s book, inspired by his 2013 Grantland column titled When We Held Kings, stands out for its firsthand accounts and insights from executives, producers, and players, and its ability to capture the broader changes that were occurring, like the hole-card camera and online poker.
The Professor, the Banker, and the Suicide King, by Michael Craig
Yet another page-turner, Craig recounts billionaire banker Andy Beal's (“The Banker”) high-stakes heads-up challenge matches from 2001-2004, against “The Syndicate”, a collection of top pros like Howard Lederer ("the Professor"), Ted Forrest ("the Suicide King"), Phil Ivey, Doyle Brunson, Chris Ferguson, and others who pooled their resources to take on Beal in heads-up matches that peaked at $20 million. Like Alvarez before him, Craig managed to capture the grittiness of the high-stakes poker world.
Ace on the River, by Barry Greenstein
Part poker primer, part life advice, Ace on the River is one of the stranger, but most thought-provoking reads on this list; it’s also the most difficult to summarize. It covers basic strategy, psychology, money management, family impacts, and moral dilemmas like addiction and integrity. It’s also the poker book I quote from the most.
Poker Tilt, by Dutch Boyd and Laurence Samuels
It took a long time for someone to write about the seat-of-the-pants early days of online poker, but that’s precisely what Dutch did with Poker Tilt — Boyd was part of one of the first online poker sites (and the first to offer tournaments), PokerSpot. This book never got the love it deserved, likely because of the controversies around Boyd and PokerSpot, but it’s a candid, fantastic look behind the curtain — probably the most honest and interesting to date.
Life’s a Gamble, by Mike Sexton
Where Boyd’s memoir looks at the failure that was PokerSpot, Sexton details the wild success of PartyPoker, a site Sexton was part of at the very beginning, and the World Poker Tour, which he was involved with from the very beginning. Life’s a Gamble blends poker history, gambling adventures, and life lessons on money, family, and addiction.
Ship It, Holla Ballas, by Jonathan Grotenstein and Storms Reback
A look at the Poker Boom from the player’s perspective, Ship It Holla Ballas follows the young prodigies, including Tom Dwan, Andrew Robl, and Phil Galfond, who dominated online poker in the early to mid-2000s, amassing millions of dollars. From their strategic discussions to extravagant parties, Grotenstein and Reback chronicle their rise from nerds to high-rollers, with their wild antics, excess, and eventual come-to-Jesus moment after Black Friday. This is one I expected to hate (I’m not a fan of or impressed by excess), but man, this was a good read.