Two weeks ago, reports surfaced that Phil Mickelson was being investigated for possible insider trading. On the face of it, the timing couldn't have been worse, with Mickelson deep in preparation for the US Open. But in a peculiar way, perhaps word of the insider trading probe was a welcome diversion for Mickelson from what would otherwise be the big storyline heading into this year's Open – his inability to win the Open. The big lefty has been runner-up at the Open six times since 1999, a record of near-misses topped only by Jack Nicklaus's seven second-place finishes at the British Open.

This year's Open is being played on the Pinehurst No. 2 course in North Carolina, where Mickelson's Open misery began. At the time, his wife Amy was nine months pregnant with the couple's first child, and Mickelson had said that if she went into labor at any point during the tournament, he was going to withdraw and fly home to be with her. The baby held off long enough for Mickelson to be beaten on the 72nd hole by Payne Stewart, who after draining the winning putt tenderly clutched Mickelson's face to both console him and to congratulate him on the pending arrival. It was a poignant moment that was rendered immortal when Stewart died in a plane crash just four months later.

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Mickelson has had bad luck at the Open, but he's also been the architect of his own misfortune, and never more so than during the 2006 Open, which was held at Winged Foot near New York. Mickelson arrived on the 18th tee Sunday holding a one-shot lead over Australia's Geoff Ogilvy. He proceeded to completely self-destruct. His tee shot was so errant it clipped the hospitality tent, his second shot hit a tree, his fourth shot sailed over the green, and he ended up with a double bogey that handed the tournament to Ogilvy. "I'm such an idiot," Mickelson said afterwards. No one in the press room that evening was inclined to argue.

With his unexpected victory at the British Open last year, Mickelson now needs only a US Open win to become just the sixth man in golf history to complete a career grand slam. But he turns 44 next Monday, and only seven players have ever won majors after the age of 44. The oldest US Open winner was Hale Irwin, who won the tournament in 1990 at the age of 45. Fifteen years after his bittersweet second-place finish at Pinehurst, Mickelson is running out of opportunities to win the title he has most coveted during his career. Of course, no one ever expected him to win the British (links golf was always a struggle for him). Mickelson has a habit of confounding expectations. At the Open, that tendency has usually expressed itself in the form of poor club selection or poor shot selection. Maybe this year, it will take the form of a long-overdue win.

With the Open back at Pinehurst this year, we thought we’d look at Mickelson's history of second-place finishes:

 
1999, Pinehurst: Mickelson held a one-shot lead with three holes to play but threw away the lead and the tournament with a three-putt bogey on the 17th.
 
2002, Bethpage Black: Mickelson started the day five strokes back of eventual winner Tiger Woods, and despite the rapturous support of the New York crowd, he never mounted a serious challenge to Woods and finished three shots back of the eventual winner.
 
2004, Shinnecock Hills: Mickelson birdied the 16th hole on Sunday to take a one-shot lead over South Africa's Retief Goosen, but he handed back the lead and surrendered the tournament with a double bogey on the 17th.

2006, Winged Foot: Needing just to par the 18th hole to claim his first Open, Mickelson instead imploded, hitting a hospitality tent with one shot, a tree with another, and landing in a bunker with a third shot, a march of folly that ultimately yielded a double bogey. NBC's ever-acerbic Johnny Miller summed it up thusly: "Right now," he said, "Ben Hogan has officially turned over in his grave." 
 
2009, Bethpage Black: After starting the final round six strokes back, Mickelson surged into contention, taking a share of the lead with an eagle on the 13th hole. But bogeys on the 15th and 17th holes halt his momentum and ultimately cost him the victory.
 
2013, Merion: An eagle on the 10th hole Sunday gave Mickelson a one-stroke lead, but a disastrous bogey on the par-3 13th hole, coupled with a brilliant back nine by eventual winner Justin Rose, dropped Mickelson to his sixth second-place finish at the Open, another chapter in his tortured history at the Open.