Ranking the Most Heartbreaking Moments of Phil Mickelson's Career

After his final-round 74 at Merion, Phil Mickelson now has a record six runner-up finishes at the U.S. Open.

Think about it: Lefty is six-times a bridesmaid at the same event. That's enough heartbreak for several careers as a professional golfer...and we haven't even touched on the other three majors, or the rest of the events on the PGA Tour.

Implosions, near-misses and chases, running out of gas, are all on this list of the most heartbreaking moments of Phil's career. 

2013 Wells Fargo Championship

Where He Stood: Entering the final round at the Wells Fargo, Phil Mickelson shared the 54-hole lead with Nick Watney.

How He Fell: Leading for much of the day, Mickelson bogeyed the 16th and 17th holes to finish one stroke out of the playoff to determine the winner. The tournament was his, but as it has so many times before, his putter betrayed him when it mattered most.

How Bad it Hurt: For Phil, who has experienced every variety of major heartbreak, the loss at the Wells Fargo was old hat. It hurt like getting atagungun (dry pepper) in your eyes. 

 2001 Masters

Where He Stood: Entering the final round, Phil Mickelson (-11) trailed Tiger Woods by a single stroke.

How He Fell: Only a stroke behind Tiger to start the day, Phil was unable to get in the way of the final leg of the Tiger Slam. Ultimately, Mickelson's final-round 70 both failed to topple Tiger and saw him lose ground to another competitor: David Duval.

How Bad it Hurt: In 2001, having never won a major, I don't think Phil realistically expected to best the greatest golfer of all time during one of the greatest stretches of his career. Phil anesthetized himself appropriately and felt very little pain.

2004 U.S. Open at Shinnecock



Where He Stood: Entering the final round of play, Mickelson was tied with Ernie Els at three under, two strokes behind leader Retief Goosen.

How He Fell: Amongst the walking wounded at Battle of Shinnecock, Phil Mickelson nearly emerged triumphant. However, leader Retief Goosen was steady, and although Mickelson matched his final-round 71, he couldn't overcome the two-stroke deficit.

How Bad it Hurt: The pain of not winning was likely not as severe as the pain of playing four rounds at Shinnecock.

2002 U.S. Open at Bethpage Black

Where He Stood: After 54 holes, Mickelson stood at even par, five strokes behind leader Tiger Woods.

How He Fell: Mickelson didn't fall, so much as he failed to mount a valiant enough charge. True, taking down Tiger on Sunday at a major was a tall order, and Mickelson did well to pull within a couple of strokes of the leader on Sunday. Phil actually bested Tiger by two strokes for the final round (70 to 72), the five-stroke deficit was simply too much.

How Bad it Hurt: Although his attempt was noble, no rational person would have expected Tiger Woods to blow a five-stroke lead on Sunday. The pain factor is a product of how hard the New York crowd pulled for Phil, and how he ultimately couldn't come through for them.

2001 PGA Championship at the Atlanta Athletic Club

Where He Stood: After the third round, Mickelson (-12) was two strokes behind leader David Toms (-14).

How He Fell: Paired with Toms for the final round, Phil Mickelson pulled even on the 15th hole. Approaching the 18th, Mickelson trailed Toms by a stroke. The latter holed a 12-footer for par, whilst Mickelson couldn't convert from over 20 feet for a birdie. Thus, Mr. Mickelson became a bridesmaid of the PGA Championship variety.

How Bad it Hurt: We're entering the "shoulda, coulda" territory here. Mickelson, long one of the best players in the game, was expected to take down Toms in the final round. The fact that he lost by only a stroke, too, is the stuff that starts to keep you up at night.

This loss was a bit more painful for Phil. Like having soap in your eyes and being blasted with a surge of hot water when attempting to rinse them.

2009 U.S. Open at Bethpage Black



Where He Stood: After 54 holes, Mickelson was at two under par. Leader Ricky Barnes stood at eight under.

How He Fell: After eagling the par-five 13th, Mickelson vaulted into the lead. However, after missing a birdie putt on the 14th, three-putting the 15th and bogeying the 17th, he finished two strokes out of the lead.

How Bad it Hurt: Like hitting your thumb with a hammer.

Entering the final round, Phil didn't seemed poised for victory. So, his failure to win isn't entirely tragic. However, his play on the back nine was filled with missed opportunities, and this was certainly a U.S. Open Lefty could have won.

1999 U.S. Open at Pinehurst



Where He Stood: After 54 holes, Mickelson (even) was one stroke behind leader Payne Stewart (-1).

How He Fell: Although he seized the lead on the 12th hole, a bogey on the 16th hole dropped him back to even with Stewart. After Stewart regained the lead with a birdie at the 17th, he famously holed his par putt on the final hole to vanquish Mickelson.

How Bad it Hurt: The first cut is the deepest, as they say. The only consolation for Mickelson: He didn't lose the 1999 U.S. Open, Payne Stewart beat him.

2013 U.S. Open at Merion

Where He Stood: Entering the final round as the only player under par, Phil Mickelson held a one-shot lead.

How He Fell: Early in the round, double bogeys at the third and fifth holes had him stumbling like the village drunk. When Mickelson blasted his tee shot at the short par-three 13th over the green en route to a bogey and added another bogey at the 15th, an uphill climb became impossible.

How Bad it Hurt: Like stepping on a rusty nail. After his improbable eagle at the 10th hole, Mickelson seemed touched by fate on Sunday at Merion. However, as he stood on the 18th tee, needing an improbable birdie to tie Justin Rose, the hurt had already begun.

At the end of the day, Mickelson's final-round 74 left him, again, on the outside looking in at another U.S. Open.

2012 Ryder Cup at Medinah



Where He (They) Stood: The U.S. team lead 10-6 entering the final day of play at the Ryder Cup.

How He Fell: Holding a one-up lead heading to the 17th hole of his match with Justin Rose. Phil Mickelson was unable to match the Englishman, who birdied the final two holes to overtake Mickelson, who lost the match one-up.

How Bad it Hurt: Like someone saying, "Close your eyes, I have a great surprise for you...it's something you'll really like," and then proceeding to clock you with a vicious haymaker, and then finding out he did he same thing to all of your friends.

The U.S. meltdown at Medinah was particularly hard on Phil since he played a key part in it. As reported by The Telegraph, Phil said: “It was one of the biggest disappointments that I’ve had to deal with throughout my career."

 2006 U.S. Open at Winged Foot



Where He Stood: After 54 holes, Phil was tied for the lead with Kenneth Ferrie at two over par.

How He Fell: Phil needed par on the final hole to secure his first U.S. Open victory. What followed, was neither a par nor a series of good decisions. He (inexplicably) hit driver, which ended up in a tent. He went for a heroic recovery shot, which didn't work. In the end, he double bogeyed the hole.

How Bad it Hurt: Mickelson's collapse at Winged Foot hurt worse than a root canal without anesthetic...performed on yourself.

Phil has never been closer to a U.S. Open victory. He has also never melted down so epically.

As Mickelson himself said so succinctly following the loss, "I am such an idiot."