the legend lives on

Payne Stewart almost sold his mansion to Michael Jackson, plus other insane stories from the golf legend

On the 25th anniversary of his passing, there are fun ways to remember the three-time major winner
October 24, 2024
PGA TOUR Archive
Payne Stewart, circa 1995.  PGA TOUR Archive

Payne Stewart tragically passed away 25 years ago this week at age 42. Even so, he lived more in four decades than most of people could ever dream of. Born and raised in Springfield, Mo., the three-time major champion has statues of himself around the world, victories on multiple continents and a look that remains instantly linked to his name.

There will be plenty of tributes and remembrances, including our own included, for the iconic athlete, but how many of them will include the time he nearly sold his house to Michael Jackson … a very real thing that almost happened.

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(Golf Digest+ members get access to the complete Golf Digest archive dating back to 1950. Sign up here.)

In the June 1999 issue of Golf Digest magazine, Guy Yocom sat down with Stewart to discuss everything under the sun: golf dry spells, equipment changes and favorite Ryder Cup captains. But, there was only one possible anecdote to lead with. Everything else paled in comparison.

“When Payne Stewart recently put his Orlando mansion up for sale, one of the prospective buyers was pop singer Michael Jackson,” Yocom wrote. “As Jackson toured the house, his manager informed him the seller was ‘the famous golfer, Payne Stewart.’ Jackson was clueless at first, and then his manager told him Stewart was the golfer who wore colorful knickers. ‘Oh, that guy,’ Jackson said. ‘I know who he is.’”

It’s pretty tough to mix up the always colorful Stewart (figuratively and literally) with his golf brethren. Even the King of Pop could place him in between record-setting albums and worldwide tours.

“It was funny. Aaron had some music playing in his bedroom, and when we showed Michael the room, he started dancing a bit, just moving with the music,” Stewart said. “He didn’t have a clue who I was or what I did for a living. Then his manager explained that I was the golfer who wore knickers.”

Going back through the Golf Digest archives, it’s clear Stewart had quite a fascinating relationship with GD. To be fair, that’s what’ll happen when you shoot a cover featuring a chimpanzee.

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“If you can’t laugh at yourself, then how can you laugh at anybody else?” Stewart once asked.

Dubbed “Golf’s Great Gatsby,” Stewart would speak to someone at GD every so often and as luck would have it tell a once-in-a-lifetime story every few months.

Maybe it’s how he went to Malaysia to golf and somehow met his eventual wife (a lissome blonde vacationing in Malaysia to watch her brother play golf) or how he first wore his patented knickers while teeing off with Lee Trevino (“Lee kidded me when he first saw them, of course, but later he told me they really looked sharp”), every Stewart story could be adapted into its own movie, or at least short film.

The GD Archive is good for a lot of things, but the Stewart catalog just keeps the hits coming. Anyone can get lost in the tales for hours. We already did; it definitely will happen to you, too.