There’s a reason why Phil Mickelson has been labeled the biggest cry baby in sport. In 2004, he was the world number one golfer, and had been the victor of a major tournament just months prior. He was winning tournaments left and right, but had yet to be victorious at the PGA Championship. On his way to the title, Phil chipped in from the side of the fairway, giving him a 10-footer for the birdie that would tie the match, and ultimately seal the championship. However, it was Keegan Bradley who did the honors, and he did it with a smile. He said that he was going to win, and that he would do it by simply putting the ball close to the
Phil Mickelson was on the cusp of winning his first major last year, until he sucked at the playoff stage and lost to Keegan Bradley. The PGA Championship was supposed to be the event that propelled Phil to the top of golfing world—and it did for Keegan Bradley. Just two months later, Mickelson was caught on video taking $10,000 from Bradley after predicting a hole-out in their playoff match. Bradley made a point of saying that Mickelson was in denial after losing the championship, but there are other reasons to doubt Mickelson’s recent behavior.
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Phil Mickelson likes to make the practice rounds of the PGA Tour interesting by adding a gambling element. In fact, you may not even have to spend a few hundred or thousand dollars if you agree to a pre-tournament spin with Lefty. Throughout his professional golf career, Mickelson has had countless anecdotes about his famous Tuesday Money matches, but the one about his match with former PGA Championship winner Keegan Bradley is the pinnacle.
Phil Mickelson and Keegan Bradley are good friends on the PGA Tour
Phil Mickelson and Keegan Bradley make the hole flat during the 39th hole. Ryder Cups at Medina Country Club in 2012 | Ross Kinnaird/Getty Images 
COMPARED TO: Phil Mickelson was in the top 100 of the world ranking list for more than 27 years, but never reached the top Mickelson and Bradley have a rich history of rivalry between them. They played two Ryder Cups and a Presidents Cup together and were a great team. The two PGA Tour veterans have combined for a 6-2-1 record in nine team matches for the U.S. Bradley said playing with Mickelson was one of the most rewarding experiences of his playing career. I enjoyed playing with Phil for a number of reasons, Bradley said on the 2020 Subpar Golf Podcast. First, with the changeover, I knew I could hit anywhere. He hit a shot [to get out of a problematic situation] or I missed the green and he chipped from three feet. And another thing – with the best ball, my power is to hit it pretty straight down the fairway. And Phil throws here and there, and hits ten feet out of the woods. I loved the dynamic of our partnership and was more than willing to let Phil take the reins and he was the boss. He’s just the best. He’s just a funny guy. But Bradley’s longtime friendship with Mickelson doesn’t make him immune to big bets on the course.
Mickelson once accurately predicted how Bradley would squander his advantage in amoney match
. COMPARED TO: Tiger Woods was once called to the golf course in the name of his country Mickelson and Bradley have had their matches over the years, and Lefty always came out on top. In a Tuesday night match between Bradley and Kevin Stralman and Mickelson and Rickie Fowler a few years ago, Bradley finally had a chance to beat his lifelong opponent, but Phil used psychological games and a crystal ball to get in his head. Mickelson told this amusing story to Alan Shipnak during the 2017 GOLF.com podcast. Now Keegan is ready to walk away from these games because he never won. It’s been a year and a half now, and he pays every time. And it becomes demoralizing. And he said: If I don’t win today, I’m out. Today is the day. Today is the day I win. On to 12. Green. Keegan and I do about 0 and 0, and I leave. You’re down to two positions. And when I get over that blow, I step back and say: Oh my god, this move is the whole game. And Keegan bit down and said: Oh, yeah? How’s that? That’s exactly what I was hoping he would say. And I said: If I miss, you make your move. You’re full of go. You’re going to get there, and you’re going to get three points with six minutes to go, and you’re going to win. But if I cook it, the ass is out in no time. You’re going to be so angry that you and Brendan are going to put a hole in us. The next thing you know, we’re tied, Ricky and I have the momentum, we make a birdie or two on the drive and probably hit, 2 and 1. And that’s exactly what happened.
Phil’s prediction came true
. COMPARED TO: Phil Mickelson: Left-handed winning percentage in top divisions Mickelson’s intelligent commentary apparently moved Bradley greatly, and Lefty’s prediction came true exactly as he said it would. So I hammer it out. I hit the ball, Mickelson continued. And what he may have missed on the side, he missed below. He quickly erased it on the negative side. Now they’re so angry. They both make a bogey on the next hole and we skip that hole and now we are tied. Ricky and I make birdies on 15, 16 and 17 and win by 2 and 1. And this story makes me laugh every time I hear it, because it’s just funny. And I don’t care about the money. I love being able to do that – and I beat him to it every time I see it. Note to self: Never play with Phil Mickelson on the golf course.
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