Sept. 25-Oct. 1, 2023 Marco Simone Golf & Country Club, Rome, Italy

Where do you start when trying to describe the 1999 Ryder Cup USA team shirt – a piece of clothing that's more crowded with historical pictures than your grandma's fridge, has been sold for nearly $2,000 and was worn for arguably the greatest comeback in Ryder Cup history?

Well, how about we start with a picture of the shirt itself. Here's David Duval wearing it mid-comeback in Brookline, Massachusetts. (By the way, it's infamous enough that hardcore golf fans will simply know this shirt by the description, "The Shirt.")


Before we go any further, let's set the scene in case you are not familiar with it: the Europeans are leading the Americans 10-6 heading into Sunday at The Country Club in Brookline. They needed to win just four matches – half as many as the Americans – to win the Ryder Cup. But the Americans weren't discouraged.

The night before the historic comeback, Ryder Cup USA Captain Ben Crenshaw made what became his famous prediction, "I'm going to leave y'all with one thought, then I'm going to leave. I'm a big believer in fate."

"I have a good feeling about this," he said, winking and wagging his finger, "that's all I'm going to tell you."

If you have the confidence to create burgundy uniforms with more than half a century of framed, black-and-white pictures of past American Ryder Cup-winning teams (Crenshaw oversaw the design of the shirts, according to ESPN's Mark Soltau, who years later wrote about where all of the 1999 Ryder Cup USA team members kept their version of The Shirt), then it's understandable that you'd also have the confidence to predict your team overcoming a historic deficit on the golf course.

The next day the Americans won their first six matches and rallied to win 14.5 to 13.5 – setting the record for the biggest comeback win in the history on the final day of the Ryder Cup.

"I've been so lucky in my life," you can see Crenshaw say below. "But to be the captain there was a distinct honor and privilege."

The tides turned when Leonard sank nearly a 50-foot putt on the 17th green, causing American players, spectators, wives and media to spill onto the green in hysteria, disrupting Jose Maria Olazabal's impending birdie putt, which he later missed once the green was cleared. Leonard's make and Olazabal's miss all but clinched the Ryder Cup for the U.S. team.

"If you don't find your own motivation to play in the Ryder Cup, there's something wrong with you," Leonard said. "You don't belong playing there."

Let's take a closer look at Crenshaw's craftsmanship and what winning Ryder Cup teams he chose to display on his beautifully ugly creation.

A picture of the Ryder Cup is featured throughout the shirt – next to the bottom button, right shoulder, right abdomen and left bicep, among other places. A picture of the victorious 1935 American Ryder Cup team is around belly-button level near the bottom of the shirt. The winning 1937 team is to its right, if you're facing the shirt, and the 1947 team is to the upper left. The 1951 American team is on the left breast of the shirt.

"It wasn't a beautiful shirt, but I thought it was cool," Jim Furyk told Soltau. "It had a lot of emotion and time spent on it by Ben (Crenshaw)."

There's a patterned, beige collar and sleeve cuffs.


Most of the shirts rarely see the light of day, however. Eight of the 13 Ryder Cup USA team members told ESPN that The Shirt is in a closet or packed away in storage. Three said they don't know where it is. Steve Pate had his framed and sold in a charity auction.

That leaves one final Ryder Cup team member – Tiger Woods.

"I threw it in the fireplace over Christmas and burned it," Woods told ESPN. "It was sooo ugly. It provided more warmth for the house."

But those never-say-die American golfers who celebrated in 1999 aren't the only ones who own The Shirt.

In 2018, one of the team-issued shirts was sold for $1,951.20. It wasn't signed by all of the American golfers. It wasn't worn by Ryder Cup USA Captain Ben Crenshaw. It was simply an official team-used shirt from the Ryder Cup.


The starting bid was $200 and bids slowly increased in modest increments – first $20, then $22. But if you want The Shirt, you can't mess around with simply adding an extra Andrew Jackson to the bill and hope to win. After two days on inactivity, someone raised the bidding to $759, only for another bidder to immediately counter with a $251 increase to $1,010.

For the price of roughly 450 brand new Titleist Pro V1 golf balls, someone bought The Shirt for nearly $2,000.

If you're a golf history buff and you have both the cash to buy The Shirt and the courage to wear it, good on you. Because you're one of the few – not even Leonard wears The Shirt anymore.

"I don't think it's going to get back into the rotation," Leonard told ESPN. "We never wear any of those things again."

WATCH BELOW: The best shots (and the shirt) from that Sunday in 1999

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