Bing Crosby’s golf bet with man with a mysterious past

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. Continue reading

Magicians on the European Tour

Promo video for the European Tour with some amazing tricks (I’m still not sure how he catches that ball) but perhaps the most impressive one was hitting an approach off the back of the club to within 15 ft of the hole. (Click here if you don’t see the player below).

There have been magicians on the pro tour for some time – check out this highlight of Seve Ballasteros putting magic at a 1984 exhibition match. (Click Here if you don’t see the player below).

The History of Betting in Golf: Let’s make it a little more interesting


There is little that can better spice up a good golf game than waging a little bet with friends. Most of us keep it small and simple, betting a couple of bucks or a round of drinks. However, golf folklore is infamous for costly, outrageous, and just plain wacky bets.


Have you ever bet that you could make a hole in fewer strokes than your partner? So did Sir David Moncreiffe and John Whyte-Melville in 1870, but they probably played with a little higher stakes than your average bet. The records of The Royal and Ancient Golf Club of St. Andrews report that the bet was literally life or death and the loser had to die. Although the records omit the outcome of the match, it is recorded that 13 years later, John Whyte-Melville gave a speech where he lamented “the causes that led to…” the death of Sir David Moncreiffe.

Such wagers in early Scottish golf were not uncommon, especially among the aristocratic class. Restrictions were even formally set by the Honourable Company in the mid-18th century to limit the amount one could bet on a game of golf, but were not followed as elite gentlemen continued to play for large sums.

In the early 20th century, golf bets became less extreme but far more unusual. There are stories of a man who bet he could win a game wearing a suit of armor, and another of a man who bet he could score under 90 in a dense fog.

There are also tales of golf debauchery in order to make sure a bet to swings in one’s favor. Infamous gambler, Titanic Thompson, bet that he could sink a hole in one 40 feet away. His poor opponent probably gawked in amazement as he made it in, unaware that Titanic payed a greenskeeper to lay a track straight to the hole. Don’t get any ideas!


More about Titanic Thompson, the man who could “sink” everybody.