major riddle, the biggest fish of all time!!

Throughout poker’s history there have been fish and there have been whales (much larger fish), and then there was Major Riddle, the most celebrated loser the game has ever known.

Like that of his rival fish, Rex Cauble and Jimmy Chagra, Riddle’s abysmal play at the poker table stemmed mostly from the fact that he had more money than he knew what to do with. After growing up in Kentucky and Indiana, he moved to Chicago and started a trucking company that became one of the most prominent in the Midwest. While everyone was going broke during the Depression, Riddle grew fabulously wealthy. Not all the money he made was on the up and up, however. He was often linked with the mob and was not above his own dirty dealings. He allegedly made his drivers buy their trucks from him on a payment plan, and just as they were nearly done paying off the loan Riddle would fire them and repossess the trucks.

In 1956, he left Chicago and moved to the burgeoning town of Las Vegas, Nevada where he bought the struggling Dunes Hotel. Together with Bill Miller, Riddle began devising ways to make the hotel more financially stable. One of his more successful ideas was hosting the famed Minsky’s Follies in 1957, making Riddle the first man to stage a topless cabaret on the Strip. Despite the uproar in the State Legislature, the show attracted 16,000 customers in a single week, a record that stood for over 30 years.

When Riddle wasn’t busy overseeing the management of his hotel, he could usually be found sitting in a card game, and if he was in the game you could be sure that the table would be full and have a long waiting list. Not only was he a bad player with deep pockets, he was also easily cheated. The notorious mobster Tony Spilotro, along with a couple of his cronies, habitually took thousands of dollars off Riddle using the “three-pluck-one” scam. Others conned Riddle into taking proposition bets he had very little chance of winning.

Even when the game was played straight, Riddle rarely won. A stud player for most of his life, he suffered his biggest losses against the road gamblers from Texas while trying to learn their game, no-limit Texas hold’em. One hand in particular illustrates just how steep the learning curve was for him. Sitting in a game at the Dunes, he got involved in a big pot with Johnny Moss, which was his first mistake because Moss was still at the top of his game at the time.

The flop came K-K-9, and Moss led out with a bet. Everyone folded except for Riddle who called. The turn brought another nine. Once again Moss bet and Riddle called. When a jack fell on the river, Moss shoved the last of his money into the pot, and without any hesitation Riddle called. There was over $300,000 in the pot. Moss flipped over pocket nines, giving him four of a kind. Riddle showed — wait for it — pocket deuces!

Everyone at the table did his best not to bust out laughing. Riddle could not even beat the board, a fact that Joe Rubino, a bookmaker from Alabama, made the mistake of verbalizing, before adding, “He shouldn’t lose that last bet.” By Rubino’s logic, Riddle should have been allowed to take his last call back because he couldn’t beat the board with the hand he had.

Rubino’s intrusion in a hand he wasn’t even involved in didn’t go over very well with Moss. Irritable on his good days, Moss exploded. “What the ell are you talking about?” he snapped at Rubino.

“He can’t beat the board.”

“You know so little about the game you don’t even realize that sometimes the board is the best hand. Now mind your own business and stay out of mine, or you’re not going to like it very much.” 

Riddle’s lack of skill didn’t stop him from betting all that he had whenever he got a chance. While playing at the Sahara, he once raised a pot using a napkin with the title to the Dunes written on it. Riddle won that hand, but thanks to that sort of recklessness his hold on his hotel grew increasingly tenuous. When the big game moved from the Dunes to the Aladdin, Riddle followed it across the street, and it was there that he lost control of his hotel for good. In less than a year he went from owning seven-eighths of the Dunes to owning just an eighth. The rest he lost at the poker table.

Just as he’d done on countless occasions before, Riddle shrugged off the loss and moved on to a new venture. In 1977, he bought the Thunderbird Casino and renamed it the Silverbird. He recruited Eric Drache and Doyle Brunson to spread a high-stakes game there, but the game never acquired quite the same luster as the one formerly played at the Dunes and then the Aladdin. At the Silverbird one could lose a car or perhaps even a house, but not an entire casino.

Major Riddle died in 1980, and with him passed one of the last vestiges of the old Las Vegas and by most accounts the biggest fish the game of poker has ever known.