You wouldn’t call Rory McIlroy a golf historian, but he does have an abiding curiosity about the game’s major championships. I am thinking of a moment a few years ago, when my friend Mike Donald and I ran into the lad at the Bear’s Club, a Jack Nicklaus enterprise in South Florida. When I introduced Mike to Rory, I detected just a hint of recognition on his map-of-Ireland face. Mike won one Tour event, in 1989, the year Rory was born, and my sense was that Rory knew Mike’s name. Beyond that he seemed to be drawing a blank.

The next day I saw Rory in the locker room at the Honda Classic. He was the reigning U.S. Open champion, and I asked him if he knew anything about Mike’s U.S. Open highlight. He didn’t, but he was happy to learn something.

“In the ’90 Open at Medinah, Mike lost to Hale Irwin in a 19-hole playoff,” I said. In other words Mike was one shot away from having his name on the trophy that was then in Rory’s possession. I reached for language I knew Rory would understand. “Mike was Rocco before there was a Rocco.”

For you kids out there: In the 2008 U.S. Open at Torrey Pines, Rocco Mediate, working-class Tour player, was tied with Tiger Woods, the ultimate golfing Brahmin, after 72 holes. They remained tied after an 18-hole Monday playoff. Mediate then lost on the first hole of sudden death. Irwin in 1990 was already a slam-dunk Hall of Famer. Donald was, as his friend Jack Welch once called him, “a grunt.” (A compliment from the then GE boss.) The progenitor of both of these mano-a-mano playoff mismatches was Ben Hogan vs. Jack Fleck at the ’55 Open at Olympic, except in that one David beat Goliath. Open playoffs — drawn-out afternoon affairs, 18 holes at a minimum, often contested in stifling heat — are memorable. There’s the first act, to get into it. The second act, the playoff itself. And the third, the what-could-have-been act. It is true theater. As much as anything in golf, Open playoffs brush against the nub of life.

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Rory didn’t need a playoff at Congressional in 2011. He won his U.S. Open by eight. Still, upon learning about the 91-hole Open in 1990, he nodded knowingly.

The Sunday afternoon of that Open, celebrating its silver anniversary this year, unfolded like a long, tense movie. Dave Marr reminded TV viewers more than once that almost a dozen guys were in position to match or beat the 45-year-old Irwin, who was in the house early at eight under. (Raise your hand if you remember when the Open was on ABC.) Phil Mickelson and David Duval, each playing in his first Open, were vying for low amateur. Nicklaus, already a winner on the Senior tour, had shot a stop-time, third-round 68. Nick Faldo, high priest of fairways-and-greens golf, finished a shot out of the playoff. Greg Norman, still using a wooden driver, shot a pair of 69s on the weekend. Curtis Strange was looking to win his third consecutive Open. Medinah ’90 has had legs.

Mickelson arrived in Chicago as a teenager and turned 20 on U.S. Open Saturday. Jim Mackay, newly nicknamed Bones, was caddying for Larry Mize that week and remembers hearing fans sing “Happy Birthday” to his future boss from across a fairway. Mickelson remembers the punishing rough, his solid play, the challenge and the excitement.

“I got to three under through 14 on Sunday, and I felt like I had a chance to win the national Open,” Mickelson said recently. “Nobody else would say I was really in it, but that’s how I felt.”

Young Phil leaked oil over the final four holes, but he still shot even par and was the low amateur, five shots ahead of Duval. Mickelson left town believing he would someday win the Open, and nothing has changed since. “I’m going to Chambers Bay still thinking I can win a U.S. Open,” he said. “Or my second British Open,” a nod to a course that is brackish, wide and windblown. Medinah in 1990, he said, “feels like yesterday, maybe five years ago, tops.” The persistent question, Mickelson said, through all these years is this: “When do you stop learning and start executing and win the damn thing?”

Medinah was the first U.S. Open for Mike Davis as well, at least as a USGA employee. He was 25 then and just starting his career in Far Hills. Now he is the USGA’s executive director, and Chambers Bay is his baby as much as anybody else’s, at least until the opening bell goes off. Davis, like Donald, played college golf at Georgia Southern, but a decade later.

“When Mike and Hale went to the first tee to play that 19th hole, my radio went off,” Davis said recently. “There wasn’t a pin on the 1st green! The flagsticks had already been collected, from the first time they went through. I grabbed the flagstick off the 18th green and ran it over to the 1st green. If you look at the pictures from that last hole, you can see the flag has 18 on it.” Eighteen years later Davis would be the USGA official overseeing the Woods-Mediate playoff at Torrey.

On that Monday at Medinah, Donald and Irwin each shot 74, two over. Irwin made a par on 18, Donald a bogey, and they signed their cards. P.J. Boatwright, the USGA executive officiating the playoff, then gave Irwin the honor when they returned to the 1st, because of the scores on 18. Donald argued that they had just completed a stroke-play round and were going to begin a different competition, this one being played in sudden death, which the USGA had never had to use before. Boatwright then said Irwin would play first because he had the honor at the day’s start. Donald said they should draw for the honor. Tour players typically want to play first in such situations. You drive it in play, you put pressure on the other guy to do the same.

Boatwright, working what would be his final Open (he died in 1991), rejected Donald’s argument. It was the second rules brush between the two in a matter of months. During the second round at the Masters, Donald hit a stubby snap-hook off the 18th tee. His ball bounced off a restroom roof and disappeared into a drain. Donald sought a free drop, but Boatwright made him play as if his ball had finished in a water hazard. Boatwright had to know what Donald, called Mad Dog by some of the Tour caddies, thought of his ruling. It’s worth noting that Donald was on his way to shooting 82 that day and answered every last question from reporters, just as he had done the first day, when he shot 64.

That week Donald caught the eye of the great Jim Murray of The Los Angeles Times, who, in a USA Today poll at Medinah, picked Donald, then 34, to win. The man was a genius. In his column for the Monday of the playoff, Murray wrote, “If [Donald] wins, I’ll try not to say I told you so. Nobody likes know-it-alls. But I had him in the pool, too.”

Murray was surely watching when Irwin, Donald and Boatwright assembled on the 1st tee for the second time on that Monday, for the day’s 19th hole. Irwin hit it right down the sprinkler line. He followed with a sand iron (his phrase) to about 10 feet and made the putt for three that won him his third U.S. Open. He was the oldest player to win an Open and the first to win playing on a special exemption granted by the gents in Far Hills.

Donald, who had about a four-footer for par, picked up his marker and plucked Irwin’s ball out of the hole while the champ did a little dance. “My game opened up like an accordion, and I made some beautiful music,” Irwin said years later of his play at Medinah. Donald figured Irwin would want his game ball. He knew its significance. Only four men had won four Opens: Nicklaus, Hogan, Bobby Jones

Source: https://golf.com/news/1990-us-open-hale-irwin-mike-donald-and-the-first-19-hole-us-open-playoff/