This is the talk I gave at Bet Bash earlier this month. As I state at the beginning, this isn’t a comprehensive history or even a scholarly one. It’s merely a collection of anecdotes and stories I found surprising and interesting as I’ve researched this topic over the last couple of years. Folks at Bet Bash seemed to enjoy it and encouraged me to do it again, so I’ve recorded it here for paying subscribers. If you’re not already a paid subscriber and you’d like to watch, you can sign up with this link:

If you’d like a more involved or comprehensive treatment of this topic, here’s a short bibliography of books I mention in this talk or that I found useful while researching it:

Over/Under: An Unexpected History of Sports Betting by David Bockino

Sports Betting and Bookmaking: An American History by Arne Lang

Roll the Bones: A History of Gambling by David Schwartz

Play the Devil: A History of Gambling in the United States from 1492 to 1955 by Henry Chafetz

And don’t forget you can buy any of the books mentioned here on this substack or on the podcast at our bookshop: https://bookshop.org/lists/american-gambler-book-club

Jay Cohen was one of the founders of World Sports Exchange in 1997, the first ever fully online sports betting site. In 2000 he was the first person ever convicted of violating the federal Wire Act for running an online sportsbook, despite the fact that his company was fully established and licensed in Antigua and that he built it with the advice of an army of lawyers, accountants and consultants to make sure he wasn’t breaking any American laws. Cohen was the only American offshore operator to come back to the United States and plead Not Guilty and fight the case. He lost and served 18 months in federal prison. Odds Man Out is the story not only of how he built World Sports Exchange, but of the years-long trial where he did battle with the U.S. government and the major sports leagues to defend his business and clear his name.

Buy Odds Man Out

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Elon University professor David Bockino’s new book on the history of sports gambling makes the case that sports in America aren’t corrupted by gambling - but owe their very existence to the undeniable American urge to gamble. He joins me on this episode to discuss his book and his research.

Buy Over/Under: An Unexpected History of Sports Gambling

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I finally broke my standing rule of “No Fiction” in this episode to read Bernard Malamud’s debut novel The Natural. If you’ve seen the 1984 film adaptation starring Robert Redford but, like me, had never read the novel, you will be shocked at how radically different the story in the 1952 novel is from that of the feel-good film. Joining me to discuss is the co-host of the No Homework podcast Charles Star. We recorded this episode live from the cheap seats at a Mets game with terrible microphones, so just pretend it’s 1952 and cut me a break if it sounds bad.

Listen to No Homework

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Nate Silver’s 2024 bestseller On the Edge: Risking it All is a deep-dive into the philosophical and cultural underpinnings of our modern-day gambling-obsessed America. In nearly six hundred pages he examines everything from poker to cryptocurrency to AI, and presents an ontology that divides American elites into “The River” and “The Village”: risk-takers and risk-averse. Joining me to discuss it is the chess and poker player Jennifer Shahade, author of the new book Thinking Sideways: How to Think Like a Chess Player and Win at Life.

Buy Thinking Sideways

Buy On the Edge

Subscribe to Jen’s Substack

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American Gambler is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

Our current book club pick is Something for Nothing: Luck in America by Jackson Lears. We’re trying something new for this book: weekly livestream discussions. Tune in live each week to watch for free or subscribe and get access to the archived videos. This week we continue with a discussion of Chapters 4 & 5.

American Gambler is a reader-supported publ…

Our current book club pick is Something for Nothing: Luck in America by Jackson Lears. We’re trying something new for this book: weekly livestream discussions. Tune in live each week on Mondays at 2pm to watch or subscribe and get access to the archive. This week we kick it off with a discussion of the Introduction and Chapters 1-3.

Two experimental economists spent decades studying the way human beings evaluate risk and probability by doing gambling experiments on people all over the world. Then they repeated those experiments with elephants. What they learned might hold the key to some of humanity's most pressing issues - including climate change.

This week we read The Gambling Animal: Humanity’s Evolutionary Winning Streak - and How We Risk It All by Don Ross and Glenn Harrison. My guest to discuss it is the London based senior writer at Bloomberg Kit Chellel, whose new book Lucky Devils: The True Story of Three Rebel Gamblers Who Beat the Odds and Changed the Game is out this week.

Buy Lucky Devils

Buy The Gambling Animal

Read an excerpt of Lucky Devils at Bloomberg

American Gambler is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

After reading the recent Atlantic cover story on sports gambling I knew I needed to vent about it to someone, so I asked my friend Danny Funt to come on my substack and have a friendly debate about it. He’s the author of the book Everybody Loses: The Tumultuous Rise of American Sports Gambling and has been covering the gambling beat for many years. You’ve probabl…

Gary Mayer’s first (and only?) book came out in 1974 when he was 29 years old. It was an account of the two and a half years he spent working for his bookie to pay off his debts called Bookie: My Life in Disorganized Crime. It was darkly funny and at the time it was well received. Over the years it has faded into obscurity, and its author and subject both gone with little trace of the rest of their lives. Roxy Roxborough, a former bookmaker whose life has been anything but obscure and anonymous, joins me this week to talk about Gary Mayer, “Al Talcum,” and the good old days and current strange ones.

Buy Bookie: My Life in Disorganized Crime

American Gambler Book Club SALE: Use the code BSO15 for 15% off these titles until April 1st

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