LOS ANGELES, May 1968 — On a flawless Saturday morning at Lakeside Country Club, two of America’s most beloved entertainers stepped onto the first tee with more than their reputations on the line. Dean Martin, the smooth crooner and comedy legend, and Bob Hope, the tireless USO performer and king of late-night laughs, had agreed to play 18 holes of golf for a staggering $50,000. Winner takes all.

It was the kind of bet that could only happen in Hollywood, between two men whose friendship spanned decades and whose competitive spirit was matched only by their wit. But what unfolded that day was more than just a high-stakes game—it became a masterclass in generosity, psychology, and the meaning of true victory.

The Stakes and the Players

By 1968, Bob Hope was 65 years old and an American icon. He’d been famous for over three decades, conquering radio, movies, television, and performing for troops in World War II, Korea, and Vietnam. But beneath the jokes and charitable acts was a fiercely competitive man, especially when it came to golf. Hope was known for his low handicap and relentless pursuit of improvement, often playing with presidents and moguls, and organizing charity tournaments across the country.

Dean Martin, meanwhile, was Hollywood’s natural athlete. A former boxer with effortless grace, Martin was a scratch golfer who could play par or better on most courses. For years, he’d quietly bested Hope on the links, sometimes alongside Bing Crosby or Frank Sinatra, sometimes just the two of them. And while Hope would laugh off his losses, insiders knew it gnawed at him.

So when Hope proposed a $50,000 winner-take-all match over drinks at the Friars Club, Martin didn’t hesitate. “Of losing? No. Of winning? Maybe,” he quipped—a line Hope didn’t quite understand, but would later appreciate.

The Game Begins

On the morning of the match, the two friends met at Lakeside. No gallery, no press—just two legends, a pristine course, and the weight of a wager that would make even the richest men sweat. But unbeknownst to Hope, Martin had already set a plan in motion. The night before, Dean called his accountant: “I’m going to need you to set up a $50,000 donation to St. Jude Children’s Research Hospital. Make sure it’s credited to Bob Hope, not to me.”

The accountant was baffled, but Dean’s instructions were clear. The donation would go through Sunday afternoon, in Bob Hope’s name.

As the game began, Hope was laser-focused. He hit straight, played smart, and watched as Martin—usually effortless—seemed just a little off. Drives landed in the rough, putts missed by inches, iron shots found bunkers. To any observer, Martin was simply having an off day. For Hope, it was the round of his life.

By the ninth hole, Hope was up by four strokes. By the 16th, the victory was all but certain. When his final putt dropped on the 18th, Hope pumped his fist. For the first time, he’d beaten Dean Martin fair and square.

On the green, Martin handed Hope a check for $50,000, signed with a flourish. “You earned it, pal,” Martin said, and Hope was elated. He showed it to his wife Dolores, planning to frame a copy for his office. It was, for Hope, a career-defining victory.

The Twist No One Saw Coming

But the story didn’t end there. The next morning, Hope walked into his bank to deposit the check. The teller paused, checked her screen, and delivered news that left Hope speechless. “Mr. Hope, this check has already been cashed. The funds were transferred to St. Jude Children’s Research Hospital, Memphis, Tennessee. The donation was made in your name.”

Hope staggered out of the bank, a swirl of confusion, admiration, and disbelief. Dean Martin had orchestrated the perfect play: let Hope win, give him the ego boost he’d always wanted, and then quietly donate the winnings to charity—giving Hope the credit.

Hope drove straight to Martin’s house, bypassing the usual formalities. He found Dean by the pool, drink in hand, reading the newspaper. “You sneaky bastard,” Hope said, unable to contain a smile.

Martin feigned innocence, but Hope pressed. “You let me win. You threw the game. You donated the money in my name.”

Dean sipped his drink. “Sounds like I had an off day. Sounds like you’re full of—” he laughed, leaving the truth unspoken.

Finally, Hope asked, “Why’d you do it?”

Martin’s answer was simple, and profound. “Because you’re my friend, Bob, and that win mattered to you. More than $50,000 matters to me. So, you got your win. You get credit for a big donation. St. Jude gets money for sick kids. Everybody wins.”

Hope wiped his eyes, overwhelmed by the gesture. “You’re impossible. You know that?”

“I’ve been told,” Martin replied. “And you’re not getting that money back. St. Jude has it now. It’s in my name. I’m taking credit for it.”

“Good. You should,” Martin said.

The two sat by the pool for another hour, drinking, talking, and laughing—two friends who understood each other completely.

A Hollywood Legend, A Lesson in Friendship

The story of Dean and Bob’s golf game became legend, but most people never knew the full truth. They knew Hope had finally beaten Martin and won $50,000. They knew Martin had donated the money to St. Jude in Hope’s name. But they didn’t know that Martin had lost on purpose, carefully calibrating every shot so Hope would never suspect.

Hope told the story often in his later years. “Dean Martin is the only man I know who’d let me beat him at golf, let me think I’d won fair and square, and then donate my winnings to charity in my name. That’s not just generosity. That’s psychology. That’s understanding your friend well enough to give them exactly what they need and making them better for it.”

When Dean Martin died in 1995, Bob Hope spoke at his memorial service and shared the story. By the end, Hope was in tears. “Dean let me win. And in doing so, he taught me something about winning that I’d never understood before. Sometimes the greatest victory isn’t beating your opponent. It’s making your opponent feel like they’ve beaten you. And then using that moment to do something good.”

The Real Victory

The lesson of Dean and Bob’s golf game isn’t about golf. It’s about knowing your friends well enough to give them what they need—even if what they need is to beat you. Martin could have won easily, could have taken the money, could have added another victory to his record. But he understood something deeper: Hope needed that win more than Martin needed the money. And sick kids at St. Jude needed the money more than either of them.

So Martin let Hope win, let him have his moment, and quietly made sure the money went where it would do the most good. That’s not weakness. That’s not letting someone else win out of pity. That’s intelligence. Emotional intelligence. Understanding people, understanding what matters.

Bob Hope got his victory. St. Jude got $50,000. And Dean Martin got the satisfaction of being the smartest, kindest guy in Hollywood.