The PGA Tour Golfer Who Won Big Betting on Bobby Jones

Did a PGA Tour golfer foresee Bobby Jones' Grand Slam in 1930, and place a bet that paid off huge? He sure did. And did a reporting mistake in the New York Times cause the Internal Revenue Service to come knocking, seeking way more in taxes than the lucky golfer actually owed? That's a popular legend, but one that doesn't hold up to scrutiny.

The story is usually told this way: Golfer Bobby Cruickshank, a highly regarded PGA Tour winner, watched Jones playing a tournament early in 1930. Afterward, enjoying drinks with sportswriter O.B. Keeler, a close of friend of Jones', Cruickshank asked if Jones' schedule for the rest of the year was set. Keeler told Cruickshank that Jones planned to play all four of the "Big 4" tournaments of the era, the tournaments later called the "Impregnable Quadrilateral" and then "the Grand Slam." Those tournaments, in 1930, were the British Amateur and British Open, the U.S. Amateur and U.S. Open.

Cruickshank was so impressed by Jones' play that he was convinced Jones would win all four of those tournaments. He contacted his father-in-law in Britain and had him place wagers — $100 for Cruickshank, $100 for dad — on Jones to win the Grand Slam.

And later in the year, when Jones did exactly that, Cruickshank and his father-in-law got to split $10,500 in winnings. However, in a comical turn of events — this is the punchline to the story, although it certainly wouldn't have been funny to Cruickshank — the New York Times reported the winnings as $105,000. And that caught the attention of the tax authorities. When the IRS came calling, they initially didn't buy Cruickshank's explanation that the actual winnings were one-tenth of what the Times reported. But eventually it was sorted out.

Is the story true? In broad strokes, much of it is true, although the real details are slightly different. The part about the New York Times getting the amount of the bet way wrong is not true, however. It just makes for a better legend.

Here is the real story. At the beginning of 1930, Jones — who, by the way, beat Cruickshank in a playoff to win his first major championship at the 1923 U.S. Open — entered several tournaments as tune-ups for the big year he had planned.

One of those tournaments was the Savannah Open in Savannah, Georgia. After following Jones for nine holes there, Cruickshank was, in fact, convinced that Jones was going to do amazing things that year.

Cruickshank later told the Associated Press that after watching Jones, he "knew the shape (Jones) was in, and made the best bet of my life."

"After I played with Bobby at Atlanta this Spring," Cruickshank said, referencing another early tournament, "I knew he could win everything he tackled this year. He was in grand shape and there's no golfer like him when he's right."

So Cruickshank did place a bet. The wager amount was $50 total, not $100 for himself and another hundred for his father-in-law. And the wager only covered three tournaments, not four. Cruickshank bet on Jones to win the British Amateur, British Open and U.S. Open in 1930.

Jones finished off that trio of wins with his 1930 U.S. Open victory, which concluded on July 12. The Associated Press story about Cruickshank's wager appeared in newspapers around the country beginning two days later, on July 14.

And the New York Times, cribbing from the AP, had a short item about the wager on July 15. But the Times did not mis-report the amount of Cruickshank's winnings. Just as the AP story had said, the Times reported, in its headline and in the article, that the amount Cruickshank won was $10,500. "Bobby's triple triumph brought Cruickshank $210 for each $1 of his own investment," the AP and the Times reported.

How much is that in today's money? Adjusting for inflation since 1930, $10,500 in 1930 equates to nearly $200,000 in 2022 dollars. And Cruickshank wasn't the only one who cashed in — his father-in-law did get half the winnings.

"I gave my father-in-law half of the bet," Cruickshank said. "But that's all right — it's all in the family."

Jones went on to complete the Grand Slam by winning the U.S. Amateur in September 1930. And Cruickshank's wager has passed into legend, too.

For more about the golfer, read our Bobby Cruickshank biography.

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