A number of golf courses in the U.S. have nineteenth holes to settle bets after completing a round. This is the "Bye Hole" at Old Palm Golf Club in Palm Beach Gardens, Florida. It’s just over 100 yards long with an island green. "Double or nothing?" Johnson Design Golf Marketing
For years, East Potomac Park was a center of money golf in Washington, DC. There are still cash games there, but the management takes a dim view of betting on the main putting green. Michael K. Bohn
Hall of Fame professional Dutch Harrison hustled on the golf course, especially as a young man. He was known in the business as an "oil artist," messing with an opponent’s head through buttery compliments. Amateur Athletic Foundation of Los Angeles
U.S. President Dwight D. Eisenhower always enjoyed a $1 or $2 Nassau. His vice president, Richard M. Nixon played some money golf, but he bent a few rules trying to improve his game. Eisenhower Library
Amateur Bobby Jones, left, had more in common than a love of the game with professionals Gene Sarazen, Bobby Cruickshank, and Walter Hagen. They all played for "a little something" during matches, even when appearing together during a war bond exhibition during World War II. Dick Johns, Middle Atlantic Section, The PGA of America
In 1933, John "Mysterious" Montague won a bet from Bing Crosby by playing with a baseball bat, rake, and shovel. After another match in the 1930s, Montague seemed pleased with his spade work on the golf course. Amateur Athletic Foundation of Los Angeles
As a young pro before joining the PGA Tour, Lee Trevino practiced playing golf with a large Dr. Pepper bottle. He became skilled enough to win money from unsuspecting pigeons. Once the story got around, Dr. Pepper signed Trevino to an endorsement contract, and the Lee played exhibitions in the late 1960s with a bottle. In this photograph, he finished his follow-through with the bottle over his left shoulder. Dr. Pepper Museum and Free Enterprise Institute
A 1920 British cigarette advertisement illustrated golf’s comfortable acceptance of a friendly wager, even in mixed company. Time & Life Pictures