Dean Martin Let Bob Hope Win $50,000 on Purpose—What He Did With the Check Made Hope Tear Up
May 1968. Lakeside Country Club, Los Angeles.
The bet was simple: Dean Martin and Bob Hope would play 18 holes of golf. Winner takes $50,000.
Bob Hope was 65 years old. He'd been trying to beat Dean Martin at golf for twenty years. And he'd almost never won.
It drove Bob crazy. Not openly. But inside, it bothered him.
How could Dean—who seemed to barely try, who showed up half-drunk, who treated golf like a casual hobby—consistently beat Bob, who practiced constantly and took it seriously?
So Bob challenged Dean to a real game. High stakes. $50,000.
Dean agreed. But here's what Bob didn't know: Dean had no intention of winning.
See, Dean understood something about Bob: Golf mattered to Bob. His ego was wrapped up in being competitive, being the best. If Dean won, Bob would be gracious. But inside, it would eat at him.
Dean didn't want that.
So Dean made a decision: I'll lose. But I'll make it look real.
For eighteen holes, Dean played just poorly enough to lose without making it obvious. He missed putts by inches. Hit drives into the rough. Played like a guy having an off day.
Bob never suspected. He just thought he was playing the best golf of his life.
When Bob won, Dean handed him a check for $50,000. Right there on the green.
Bob was thrilled. He'd FINALLY beaten Dean Martin.
The next morning, Bob went to the bank to deposit the check.
The teller looked confused: "Mr. Hope, this check has already been cashed."
Bob's smile disappeared. "What? That's impossible."
"It was cashed yesterday at 3:47 PM. The funds were transferred to St. Jude Children's Research Hospital. In your name."
Bob stood there, stunned.
Dean had donated the entire $50,000 to St. Jude. In Bob Hope's name.
Bob drove straight to Dean's house.
"You sneaky bastard."
Dean smiled: "I have no idea what you're talking about."
"You let me win. You THREW the game."
"Can you prove that?"
Bob started laughing. Because he realized what Dean had done:
Bob got his ego boost. St. Jude got $50,000. Dean got the satisfaction of outsmarting everyone.
Everybody won.
When Dean died in 1995, Bob spoke at his memorial: "Dean let me win. And in doing so, he taught me that sometimes the greatest victory is making your opponent feel like they've beaten you—and then using that moment to do something good."
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