Horses and Poker
Ernest Hemingway was one of the 20th century's best-known authors, with his career culminating with the 1954 Nobel Prize for Literature. Hemingway wrote both novels and collections of short stories, in addition to dabbling in non-fiction on occasion. Born in Illinois, he was briefly a reporter before joining the war effort in World War One. Later wars he attended as a journalist included the Spanish Civil War and World War Two, during which he witnessed the landings at Normandy on D-Day and the liberation of Paris.
In addition to the written word, Hemingway had a love of betting, and enjoyed somewhat professional wagering on horse races (which he attended regularly while living in Paris in the interwar period). Hemingway also considered himself a great poker player, and one of his stories involved a poker game in which a would-be cheater ended up being thwarted.
The Big Friendly Gambling Author
Roald Dahl is one of the world's best known children's authors, but during the course of his life he was also a war hero, serving in the Royal Air Force during the Second World War as a fighter pilot, before becoming an intelligence officer, and then wing commander. His stories are timeless classics of silly, light-hearted fun, often with deeper messages containing the ring of truth, and frequently ending in unexpected ways. Many of his works have since been translated to the big screen, such as Matilda, Fantastic Mr Fox, The BFG, and (on multiple occasions) Charlie and the Chocolate Factory.
This gambling author's love of betting is more than hinted at in The Wonderful Story of Henry Sugar, a rich fellow who is quite content to win or lose but is thrilled by gambling. Dahl himself quite liked to bet, with his daughter Lucy revealing her father taught her, and her siblings, to play blackjack and even once took her into a casino when she was just 16.
Taking Things Too Far
Undoubtedly one of the biggest names on our list of gambling authors is the Russian giant that is Fyodor Dostoevsky. Best known for works such as Crime and Punishment and the Brothers Karamazov, this 19th century writer put together numerous novels, short stories, novellas, and more during his literary career exploring the human condition. He began working with words while an engineer, translating books for additional cash, and soon started writing his own stories. Dostoevsky spent years in a Siberian prison camp, but later was able to tour Europe.
This Russian writer certainly liked gambling. In fact, he took things too far, and what should be a pleasant pastime became an addiction for him and caused him some financial difficulty. At times, he was reliant on friends and family to stave off going bankrupt. Betting's a lot of fun, but Dostoevsky is a prime example of the importance of only betting what you can afford to lose.
German-American Gambling Author and Poet
Charles Bukowski was a German-American man of letters, who wrote poetry, short stories, and novels. The humdrum world of those living in hardship in the US was the foundation of much his writing, looking at his home city of LA for inspiration regarding the drudgery of work, booze, and the ordinary lives of the poor. Not unusually for creative types, Bukowski's writing received more attention after his death than during his life - in the USA. It's another story in Europe, where the works of Bukowski, especially in Germany, made an altogether bigger impact. Bukowski was born in Germany, but moved with his family to America in 1923, shifting to Los Angeles in 1930.
The inspiration of his subject matter was generally pretty serious, but Bukowski also enjoyed betting, even going so far as to say: If you don't gamble, you'll never win. And his book Betting on the Muse puts together the story of an ordinary working man's life and hilarious stories and poetry.
The PhD Player
Maria Konnikova is yet another example of a highly educated and very intelligent individual who combines the attributes of writing talent and skill at cards. This gambling author is a Russian-American with a PhD in psychology, which might just have come in handy when it comes to reading tells and both coping with and applying pressure through bluffing. Psychology is the primary material of her published books, and in 2020 she released The Biggest Bluff, telling the story of how she learned poker from a pro, and, in so doing, understood herself better.
Her interest in poker and the best players began after reading about game theory, involving a combination of skill and luck. Konnikova certainly started with a limited understanding, not even knowing the number of cards in a deck, but by 2018 she was playing poker on a professional basis. Indeed, her love of the game actually delayed The Biggest Bluff as she was competing in more and more tournaments.
The Philosophical Bettor
Betting is nothing new, and one of our older entries on this list of gambling authors is one of the few philosophers to be a household name even today: René Descartes. Descartes was also a mathematician and scientist, and, as any serious sports or cards bettor will tell you, such a numerate and analytical mind can be a serious advantage. This 17th century father of philosophy also really knew how to let his hair down. In addition to partying, the ladies, and a spot of swordplay, Descartes also liked to gamble, perhaps fittingly for a man who also had a role laying the foundation of the scientific revolution by his status as the father of analytic geometry.
King Charles II
A Right Royal Gambling Author
King Charles II, the merry monarch, was a pivotal figure in British history in many ways. His surefooted handling of the post-commonwealth and post-puritanical era of Britain ensured that the return of the monarchy, broken for the first and only time in over a thousand years, was a success. Charles was aided by the unpopularity of both his non-royal predecessors and his younger brother, and eventual successor, James. His merry monarch nickname was well earned as he had an array of mistresses and illegitimate children (somehow managing to avoid producing a legitimate royal son to inherit the throne). Not to mention he loved lavish parties and spending big.
They call horse racing the sport of kings, and this is the area in which Charles was both a writer and a bettor. In an age where sporting rules had largely accumulated over countless years, Charles II literally wrote the rule book on horse racing, one of his great passions. But the greatest gamble he ever took was returning to Britain, when he risked his neck, and won his crown.
Musician and Gambling Author
Willie Nelson is, of course, best known as a legend of the music industry and a titan of country, but he's also a writer with more than half a dozen books to his name. The most telling of these is his autobiography, written with Bud Shrake, that tells the down to earth story of this musical maestro. In addition to his obvious fame for music, and a surprisingly large bibliography, Nelson is also something of a shark when it comes to cards.
There's a pretty well-known story in Hollywood about one such occasion, when Nelson was playing cards against his friend, actor Woody Harrelson. When well-off people play, sometimes the stakes can rise dramatically, and that was certainly the case during this game. How much the ante ended up being only the two men know, but Nelson won, and won big. In fact, Harrelson ended up losing so much cash that the country musician was able to add a new wing (the so-called Woody Wing) to his home. Just goes to show that even the wealthy should never bet what they cannot afford to lose.
The Man who Beat the Dealer
Edward Thorp is one of the gambling authors that proves that a head for figures and love of the written word can easily go hand in hand with success in both fields of endeavor. Thorp literally wrote the book on beating the dealer (cunningly entitled Beat the Dealer), which proved that card counting could overturn the house edge and make it so the advantage lay with the player in blackjack. Thorp was one smart cookie, with a doctorate, and this professor of mathematics spent time teaching at MIT.
Despite his academic standing, Thorp was no armchair professor. Instead, he put his theories into practice by playing at US casinos with real money, and finishing ahead handsomely. In 1966 he wrote Beat the Dealer, which sold 700,000 copies. Ignoring the peer review process for real world practicality connected the research to reality and engaged the public, particularly gamblers, with the importance of understanding the finer points of mathematics in betting.
Victoria Coren Mitchell
The Best British Gambling Author
While gambling has historically been seen as a man's world there are increasing numbers of highly successful female players, and top of the list for female authors is Victoria Coren Mitchell. A lady of many talents, Coren Mitchell is best known in her native Britain as the long time host of popular TV quiz show Only Connect. She's also a regular columnist for The Telegraph, and has authored numerous books including (with Charlie Skelton) Once More, with Feeling, and poker memoir For Richer, For Poorer: A Love Affair with Poker.
That memoir rather gives away that she's no mean card shark, and has achieved various milestones in her playing career. Coren Mitchell was the first poker player to win two European Poker Tour Main Events, and has total tournament winnings in excess of $2.5m, placing her fourteenth on the all time list of female poker players.
And so we finish our look at the top 10 gambling authors, from the man who wrote the rulebook on horse racing (when he wasn't reigning over Britain) to war heroes, psychologists, mathematicians, and philosophers. Smart moves can improve your odds a lot, and the smartest move of all is to keep a close eye on your bankroll.