Phil Mickelson Once Demoralized and Took Money From PGA Championship Winner Keegan Bradley by Predicting Exactly How He Would Blow a Match

Phil Mickelson loves to makes PGA Tour practice rounds interesting by adding a gambling element to the mix. In fact, you might not even have a choice to put up a few hundred or thousand bucks when you agree to a pre-tournament round with Lefty.

Mickelson has countless stories from his famed Tuesday money matches over the course of his professional golf career, but this one from a match against former PGA Championship winner Keegan Bradley takes the cake.

Phil Mickelson and Keegan Bradley are good friends on the PGA Tour

Phil Mickelson loves to gamble on the golf course, and sometimes he uses mind games to get into his competitor's head.
Phil Michelson and Keegan Bradley line up a putt during the 39th Ryder Cup at Medinah Country Club in 2012 | Ross Kinnaird/Getty Images

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Mickelson and Bradley have a rich history of competition between the two. They were partnered together in two Ryder Cups and one Presidents Cup, and they were a heck of a team. The two PGA Tour veterans went 6-2-1 together in their nine team matches playing for the United States.

Bradley said playing with Mickelson was one of the most rewarding experiences of his golf career.

“I loved playing with Phil for a couple of reasons,” Bradley explained on GOLF’s Subpar podcast in 2020. “One, in alternate shot, I knew I could hit it anywhere. He’d hit one out [of trouble] or I miss the green and he’d chip it to a foot. And the other thing is in best ball, my strength is I hit it pretty straight down the fairway. And Phil is dinging it over here or over there, and he’s hitting shots out of the woods to 10 feet. I loved our dynamic as a partnership, and I was very willing to let Phil kind of take and lead that way and he was the boss.

“He’s just the best. He’s just a fun guy to be around.”

But Bradley’s longtime friendship with Mickelson doesn’t make him immune from big bets on the course.

Mickelson once predicted exactly how Bradley would blow his lead in a money match

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Mickelson and Bradley have competed in their fair share of money matches over the years, and Lefty always comes out on top. During one Tuesday match between Bradley and Kevin Streelman and Mickelson and Rickie Fowler a few years ago, Bradley finally had a chance to beat his longtime foe, but Phil used mind games and a crystal ball to get in his head.

Mickelson told the hilarious story to Alan Shipnuck on a GOLF.com podcast in 2017.

“Now, Keegan is about ready to bow out of these games because he’s never won. It’s been a year and a half and he’s paid every time. And it gets demoralizing. So he’s like, ‘If I don’t win today, I’m out. This is the day. This is the day I’m going to win.’

“Fast forward to the 12th green. Keegan and I have about a 16-footer and 14-footer, and I’m away. Now they’re 2 up. And as I’m standing over this putt, I back away, and I say, ‘Oh my goodness, this putt is the entire match.’

“And Keegan bit, and he goes, ‘Oh yeah, how so?’ which is what I was hoping he would say.

“And I said, ‘Well, if I miss, you’re going to make your putt. You have momentum. You’re going to make it, and you’re going to be 3 up with six to go, and you guys are going to win. But if I make it, you’re going to quick-peel yours low side. You’re going to be so pissed off, you and Brendan are going to give us a hole. Next thing you know, we’re going to be tied, Rickie and I are going to have momentum, we’re going to make a birdie or two coming in, probably beat you, 2 and 1.”

And that’s exactly what happened.

Phil’s prediction came true

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Mickelson’s sly comments clearly rattled Bradley to his core, and Lefty’s prediction panned out exactly as he said it would.

“So I knock it in. I knock it in,” Mickelson continued. “And of either side he could have missed it on, he missed it low side. He quick-peeled it low side. Now they’re so pissed off. They both bogey the next hole, and we get that hole and now we’re tied. So Rickie and I birdie 15, 16, and 17, and win 2 and 1.

“And I just chuckle about the story every time I hear it, because it’s just funny. And I don’t care about the money. I just love being able to – and I give him smack about this every time I see him.”

Note to self: never gamble with Phil Mickelson on the golf course.