Legendary crooner Bing Crosby may have had a voice that was unrivaled, but it was a different story on the golf course. Crosby was no match for golf hustler John “Mysterious” Montague, even when given the upper hand. In 1937, the pair faced off in a match, in which Montague played with an unconventional set of “clubs,” including a rake, a shovel, and a baseball bat.

Montague was a happy and rotund man, who played golf and gambled with the celebrities of his day. He was the champion at Lakeside Club two years in a row, but he fervently dodged the limelight, hence his nickname. “Mysterious” Montague never discussed his past, career, and avoided getting his picture taken. On one occasion when he was likely to break the course record at Lakeside, he decided to bypass the last hole to escape the attention of the press.

Crosby, who was a five time champion at Lakeside himself, was amused when Montague suggested this off the wall bet. Bing and Montague agreed on a wager of $5 a hole, and Bing was confident that he would able to beat Montague’s equipment of junk with his seven-iron. The match ended when Montague hit the ball in with his rake for a birdie three.

Montague’s efforts to remain under the radar foiled after his triumph against Crosby. His photograph was published in the newspaper which the New Jersey police used to connect him with a 1930 roadhouse holdup. Montague was charged under his real name Laverne Moore and he was arrested. When he was on trial, his A-list buddies, including Crosby stuck by his side. Despite his swindling on the golf course, his friends argued that his clean criminal record in California showed that he had changed his ways and he was released.

After this fiasco, the golfer abandoned his mysterious and tricky ways. He continued to play golf with Bing, but stuck with regular golf clubs.

Read more about John “Mysterious” Montague and Bing Crosby and other wacky moments in golf in The Golf Hall Of Shame by Bruce Nash and Allan Zullo.

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