It’s been almost three decades since Phil Mickelson began to build his legacy, and he’s achieved feats that are nearly flawless – five-time major champion, a Players Championship in his trophy case, a mainstay on Ryder Cup and Presidents Cup squads, and almost $84 million in career earnings.

But the gaping hole on his resume, the one that always comes up this time of year, is the ever elusive U.S. Open victory.

How much of his career earnings do you think he’d give to get his hands on just one U.S. Open trophy? $5 million? $25 million? All of it?

Phil and the U.S. Open have flirted with the full borne romance several times over the last 20 years. Sometimes the two have parted mutually, citing that it’s just not the right time for either of them. Other times it’s been the tournament who ripped Phil’s heart out, smashed it into a million pieces, and took the dog and furniture before she left for good.

Let’s go back through the years of the closest times Phil ever got to destiny:

1999 – Pinehurst No. 2

While the 1999 U.S. Open wasn’t the first time Phil found himself in contention on Sunday, it was the first serious shot he had to capture the trophy. Heading into the tournament the big question hanging over his head wasn’t if he’d finally break through for a major victory, but rather if he’d even finish. The due date of his daughter was right around U.S. Open weekend and Phil was all ready to run off the golf course in case the birth was imminent.

But the baby wanted to stay in the oven just a little longer and it allowed Phil to play the entirety of the tournament. He found himself trailing by one to Payne Stewart after Saturday and the two were paired together for an epic final round showdown. The two of them swapped the lead back and forth down the Back Nine on Sunday before Payne Stewart scored a birdie on 17 to move back ahead by one.

Payne pushed his tee shot into the rough on 18, forcing him to lay up for his 2nd. Mickelson, meanwhile, bombed a drive right down the heart of the fairway and put his second shot about 20 feet below the cup. With a two-putt for par almost assured, it looked as though Phil would have to hope his child could wait one more day to say hello to the world so he could take on Payne in an 18 hole playoff on Monday.

Fate, however, had other plans. After Payne left his third 15 feet short, he buried his par putt to drive a final stake through Phil’s chances to take home his second U.S. Open trophy.

The scene on 18 saw two of the most iconic moments in U.S. Open lore. The first was Payne Stewart, on one leg, punching the air towards the cup and his winning putt fell. The second, though, was much more heartfelt. Despite how disappointed Phil felt to lose the U.S. Open in such fashion, Payne Stewart grabbed Phil by the face, both hands clasped on his cheeks, and told him how happy he was that he was going to be a dad. A truly special moment on Father’s Day weekend that pulls on the heartstrings of even the most resolute of men.

Unfortunately, the fate of each man diverged in the weeks that followed. Mickelson flew back to Arizona the following day to watch the birth of his daughter. As for Payne Stewart, though, he was tragically killed in an airplane accident four months later. But that fateful day lives on with a bronze statue of Payne overlooking the 18th green as a reminder of how special the final round of the 1999 U.S. Open was.

At the time, the golf world assumed that it would be only a matter of time before Phil Mickelson would capture a major title. Little did we know that it would take him five more years before he finally got over the hump.

2004: Shinnecock Hills

Coming off the heels of his first major victory at the 2004 Masters, Mickelson once again put himself in prime position at the top of the leaderboard and led some to ask if the floodgates were about to be opened. However, the good old folks who run the USGA had other things in mind.

Shinnecock Hills always has blustery conditions, but the fans were turned up to high for the third round. The course hadn’t seen much rainfall either and it set up perfectly for the course to dry up to ludicrously difficult conditions. The USGA had a decision to make – soak the greens in an attempt to get moisture into the putting surfaces and slow them down (as well as make them easier for competition) or let it ride and let mother nature put the golfers through the meat grinder.

Their decision not to water the greens in the 3rd round turned out to be a very poor decision – the superintendents completely lost the golf course, especially on the redan green of Hole #7. It was here where players were putting into bunkers and made even tap-ins incredibly perilous. Phil Mickelson was a victim of the USGA’s inaction, as his short par putt rolled off the green entirely and forced him to card a double bogey.

The 7th hole played just as unfairly on Sunday, and while the USGA halted play to water down the green for the group ahead of him, they choose not to for Mickelson and his playing partner. Just like the previous day, Mickelson again blew a short par putt well past the hole as it was impossible to stop anything on a downslope. It led to his second double bogey at the 7th in as many days.

Mickelson continued to battle back and managed to tie for the lead with two holes to go. However, the brutal greens once again cost him when it mattered most. He three-putted the 17th from close range for the second time in the round for yet another double bogey and hand the trophy to Retief Goosen. Even though it was Mickelson’s own undoing on the 17th that cost him the win, he holds a grudge against Mike Davis and the USGA for how they handled the 7th Green even to this day.

2006: Winged Foot

2006 saw perhaps the most gruesome, painful, and heartbreaking close call Phil has had to try and win the U.S. Open.

Phil walked up to the 18th holding a one-shot lead and his closest competitors playing ahead of him. Up ahead, Geoff Ogilvy successfully scrambled to get into the house at +5 to take the clubhouse lead. Meanwhile, Colin Montgomerie had also walked to the 18th tee with his own shot at immortality and try to break his winless drought at a major. However, he misclubbed on his approach, leaving it woefully short that led to a disappointing double-bogey 6 to end his chance for a win.

All Phil needed to do was par the last to finally get his hands on the ever elusive U.S. Open trophy. A safe fairway metal or driving iron would have sufficed to get in prime position to take aim at the green. Instead, Mickelson asked Bones McKay for the driver and careened his tee shot off the hospitality tent way, way to the left.

Despite a lucky bounce, Phil was completely obstructed from the green with two big oak trees standing in his way. He still could try and advance the ball back in the fairway, get up and down for bogey and take it to a playoff on Monday against Ogilvy. Once again, though, his brain short-circuited when he tried a hero slice around the trees that failed miserably. Like Montgomerie, Phil had one hand on the trophy and let it completely get away from him. A double bogey on the last left Phil standing at the altar alone yet again.

2009: Bethpage Black

The 2009 U.S. Open was a discombobulated mess thanks in part to dreadful weather conditions. Rain soaked the golf course for the better part of the weekend, forcing numerous weather delays and lots of start and stops for the players. The final round didn’t begin until late Sunday evening and resumed Monday morning, where Lucas Glover and Ricky Barnes held a fairly comfortable lead over the field (I’m sure NBC Sports was thrilled with that final round pairing).

Phil began his final round six back of the lead, and to get back in the thick of things he’d not only need a magical round himself but some help from guys ahead of him. Mickelson started off slow with a +1 Front Nine, but both Barnes and Glover proceeded to vomit all over themselves to bring Phil three off the lead as he made the turn. Phil put the heat on both guys by going birdie-eagle on the 12th and 13th hole to tie for the lead. However, his hot streak ended down the back nine with bogeys on 15 and 17 to fall short yet again.

The 2009 U.S. Open wasn’t the most dramatic near miss for him, but it was right there for the taking with both Glover and Barnes failing miserably on Monday. Nevertheless, Bethpage Black marks yet another close-but-no-cigar effort from Phil as his quest for a U.S. Open title would have to continue for another year.

2013: Merion

Unlike Phil’s other close calls above, he entered the final round of the 2013 U.S. Open with the 54 hole lead. Despite running under 7,000 yards on the scorecard, significant rain that softened the course and pundits calling for the U.S. Open scoring record to fall, Merion more than held its own. Thick rough and lightning fast greens allowed the course to bare its sharpest fangs and keep scores relatively in check.

The course on Sunday played brutally tough, particularly for the leaders. The average score that day was 74.5 and guys like Steve Stricker, Charl Schwartzel, Luke Donald and Rickie Fowler were all ejected from contention by the time the Front 9 was over.

The championship came down to a three horse race between Jason Day, Justin Rose and Mickelson, all of whom at one time or another held a share of the lead down the Back Nine. In the end, it was Justin Rose who prevailed, sticking a long approach on the 18th to 15 feet that ran just through the green. Rose then used a fairway metal to chip up for a tap-in par to get into the house at -1 (which, by the way, kudos to the stones it took to use a fairway metal for the biggest chip of his life).

Mickelson didn’t go down without a fight and gave his chip shot into the 18th green a run for his money. But like so many chances in the years before, he once again came home without the bacon.

*****

The 2018 U.S. Open comes back to Shinnecock Hills where Phil Mickelson will attempt to exorcise the demons to try and complete the career Grand Slam. Can he finally get over the hump? If Shinnecock Hills still had the same course setup as 2004, with the way he’s driving the ball in 2018 he’d be hard-pressed to contend, let alone even make it to the weekend. But with wider fairways than what he saw in 2004, if he can keep the ball in play and continue to putt and strike his irons as well as he has this year, it’s possible.

Yet, I can’t help but wonder if it’s too little too late for Phil. At 47 years old, I question whether he has the stamina to make it four straight days without ejecting himself out of contention. There’s a reason why the U.S. Open is considered the most grueling major of them all, and with the way, the USGA was unhappy about the birdie-fest that last year’s event turned into they should have plenty of tricks up their sleeves to make it a more usual grind.

He’ll certainly have the gallery on his side on Long Island, but it’ll remain to be seen if he can channel that energy to carry him through the weekend to finally put the cherry on top of the sundae.