The Comeback


Project 99I was there when ... American captain Ben Crenshaw leaned forward and poked his index finger in the air toward the assembled media on the eve of the greatest comeback in Ryder Cup history.

“I’m going to leave you all with one thought,” Crenshaw said before exiting the media room at The Country Club at Brookline ( Mass. ). “I’m a big believer in fate. I have a good feeling about this. That’s all I’m going to tell you.”

It was Saturday, Sept. 25, 1999, and Crenshaw’s final words that night hung powerfully in the air as he walked out. That’s because almost nothing else he said before that inspired any confidence that the Americans could overcome a 10-6 deficit in Sunday singles. In fact, right up until Crenshaw made that bold proclamation, he was rambling almost nonsensically. As articulate as Crenshaw can normally be, that’s how disconcerting the American team’s play was. Crenshaw struggled that night to make sense of how his talented cast had fallen so far behind. He struggled to explain how they were going to turn momentum around overnight.


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The week felt like a strange mix of the Academy Awards, the Olympics and rowdy British soccer.

Colin Montgomerie would attest to the British soccer comparison. It was a tough week for the Scot. This was at the height of his problems in the United States, where American fans had singled him out for derision after his confrontations with spectators at the U.S. Open at Congressional two years earlier. He was known for his rabbit ears, as a player who could easily be engaged.

After the Europeans took that commanding 10-6 lead, Montgomerie didn’t help himself.

With Saturday’s play done, Montgomerie stood in the shadow of the clubhouse reveling in Europe ’s huge lead.

“Listen,” Montgomerie told reporters. “You know we’ve won, don’t you? It’s silent. Great. That’s the best thing we can do, silence the crowd by outplaying them.”

Montgomerie couldn’t silence the hecklers in his Sunday singles match with Payne Stewart. I followed them inside the ropes that day. They were the anchor match, the final match of the competition. It would be the last time I saw Stewart play. His death in a plane crash would come exactly one month later. Watching him that day remains a terrific final memory.

In a tight match, Montgomerie battled the fans as much as he did Stewart. They hounded Montgomerie with shouts of “Mrs. Doubtfire.” I remember standing to Montgomerie’s left along the ropes on the tee box at the ninth hole. It was a tough tee shot through the trees. As Montgomerie addressed his ball, a man barked, “Don’t hit it in the woods, Monty!”

Montgomerie snarled and backed off his tee shot. The heckler, a scruffy looking college-aged kid, made the mistake of positioning himself directly behind Montgomerie’s wife at the time, Eimear. She turned and gestured to the unruly offender. Montgomerie pointed his driver at the heckler and marched toward him.

“Get rid of that man,” Montgomerie demanded to nearby security. “This is a game of golf, not football.”

Crenshaw was on the tee box, and he stepped in, steering security to do as Montgomerie demanded. Two security guards grabbed the man, stuffed him onto a golf cart and drove him away. It was the second heckler hauled away from Montgomerie’s match that day. Another man was taken away at the fifth hole. Montgomerie’s father, it came out later, was so upset at the abuse his son was receiving that he left the golf course before the match was over.

On the 13th green, with Montgomerie preparing to putt, another unruly spectator stepped forward.

Payne Stewart and Colin Montgomerie
Payne Stewart concedes his singles match to Colin Montgomerie. (Getty Images)

“Hey, Monty, your zipper’s down,” he barked.

Stewart stepped into the fray, raising his arms to still the crowd.

“That’s enough,” Stewart said. “Calm down.”

This epic final round’s best and worst moment came in front of Montgomerie and Stewart. They were standing at the 17th tee when Justin Leonard rolled in the famed 45-foot birdie putt that all but clinched the historic American comeback. The putt set off the most controversial celebration in the history of the Ryder Cup. It outraged Montgomerie and the rest of the Europeans. That’s where American players and their wives rushed the green to embrace Leonard.

With Lehman hoisting Leonard in the air, Crenshaw fell to his knees and kissed the earth, as if it were hallowed ground. He would later insist that it was just that, because it’s where Francis Ouimet was immortalized for popularizing the game in the United States. It was where Ouimet holed a birdie putt in 1913 to secure his U.S. Open upset of British stars Harry Vardon and Ted Ray.

The entire scene disgusted Montgomerie and the rest of the Europeans who saw it, because Olazabal still had a 25-foot birdie putt. Olazabal still had a chance to halve the hole and keep alive Europe’s chances of holding off the American charge.

“I couldn’t believe what I was seeing,” Montgomerie said.

European assistant captain Sam Torrance was more direct.

“It’s the most disgusting thing I’ve ever seen,” he said.

Olazabal missed the putt, helping secure what would end as a 14 ½ to 13 ½ American victory. Though the Americans had completed the largest final-round comeback in the history of the Ryder Cup, Montgomerie and Stewart weren’t done. They played on to decide who would win their match.

While Montgomerie ended up getting the better of Stewart that day, I got to see the best of Stewart. At the 18th green, with their match all square, Stewart conceded a 20-foot birdie putt to Montgomerie, giving the Scot a 1-up victory. Stewart spared Montgomerie further abuse conceding their match. I’ll remember Stewart’s act of sportsmanship, but I’ll remember his uninhibited joy that day, too. Moments later, Stewart was amid a swarm of teammates dousing each other with champagne on the clubhouse veranda.

Somewhere, Crenshaw was smiling, knowing his big belief in fate had won out.