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Phil Mickelson's Caddie Reveals Phil's Most Painful U.S. Open Loss

Caddie Jim Mackay Talks Phil Mickelson on New Podcast
On the debut episode of his new podcast, "In the Rough," Sports Illustrated senior writer Alan Shipnuck asked longtime Phil Mickelson caddie Jim 'Bones' Mackay which of Lefty's U.S. Open losses hurt the most.

As great as Phil Mickelson is, his career is missing one thing: a U.S. Open. 

He has five majors – three Masters, one Open and one PGA – but six runner-up finishes in his national championship. 

In a new podcast, Sports Illustrated senior writer Alan Shipnuck talks with Jim 'Bones' Mackay, Mickelson's caddie since 1992, to discuss which U.S. Open loss stings the most and what misread he still thinks about every day.

"It's probably a tie," Mackay says. "I would say between Shinnecock in 2004 and Pinehurst in 1999. Just because he played so amazingly well in both of them. I've been asked that question before, and people say, 'My gosh, why isn't it Winged Foot?' It's not even close to being Winged Foot. He never had it at all that week, and we were hanging on all week."

Mickelson double-bogeyed the 72nd hole in the 2006 U.S. Open at Winged Foot when a par would have won the tournament. Mickelson double-bogeyed the 71st hole in the 2004 U.S. Open at Shinnecock after his ball was next to a rock in a greenside bunker and finished two shots back. The 1999 U.S. Open was the memorable duel between Mickelson and Payne Stewart where Stewart won by a single stroke.

"At Pinehurst, it was so surreal," Mackay says. "You're out there in the mist, and it's like being on a movie set. At that point, he hadn't won a major, and Amy was incredibly pregnant. Phil played so incredibly well and got beat by a guy who made the greatest par putt I've ever seen on 16, then birdied 17 and made a putt on 18. It was a tough pill to swallow."

MORE PHIL: An Oral History of The 1999 U.S. Open By Alan Shipnuck

Mackay still blames himself for Mickelson's misssed birdie putt on the 17th hole that was the turning point of the match.

"Phil brought me in for the read," Mackay says. "We both thought it was pretty straight. He hit the putt, and I've only seen it once or twice on video, but it broke definitively to the right and didn't go in. Payne makes the birdie putt to go one ahead, which was the difference in the tournament. There's not a day that goes by that I don't think about that, and if I had a do-over in my career, it would be that read."

MORE PHIL: The Reason Phil Mickelson Has Never Won A U.S. Open

Shipnuck puts Mackay's mind at ease: "I asked Phil. He says he pulled it." 

"Did he really?" Mackay says. "There you go, I've never asked him. That's not something you talk about with your player there in the moment."

Mickelson will have a chance to add a U.S. Open title in June when the national title heads to Chambers Bay, outside Seattle. 

Welcome to the debut episode of Alan Shipnuck's In the Rough!

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