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Which games from this season will haunt the Yankees the most?

The Yankees will finish just out of the running for the playoffs. Which games from this season will they rue the most?

MLB: New York Yankees at Boston Red Sox David Butler II-USA TODAY Sports

With the Orioles’ victory last night in Toronto, the Yankees were eliminated from playoff contention. That the Yankees remained mathematically alive for this long is a bit of an achievement in and of itself. 2016 will probably be remembered as the year the Yankees sold for the first time in ages, which makes their late season relevance all the more impressive.

They will come up a couple games short, but this is one of the rare cases where there is plenty of solace in narrowly missing the playoffs. Still, the Yankees came close, and when a team comes close, there is always at least some wondering about what might have been.

What might have happened if this player didn’t get hurt? If this player wasn’t traded? Or, what might might have happened if they didn’t blow this game or that game? In a season that will end with the Yankees just a few games out of the playoffs, let’s remember the games that will haunt New York the most, the victories that were so thoroughly within their grasp that it’s hard to imagine they actually lost.

May 5th, 2016- New York 0, Baltimore 1

Originally, I set out to highlight the games the Yankees lost despite possessing a remarkably high win probability at some point. There will be plenty of that later, but I thought it better to start with the game that marked this season’s nadir. A one-run shutout loss in Baltimore, the Yankees’ seventh loss in eight games, and one which dropped them to a season low eight games below .500 at 9-17.

That stretch of losses in late April and early May is what ultimately doomed the Yankees this year. The Yankees went 73-59 after losing this game, but it wasn’t enough to dig out of the hole. This game, a ten-inning affair they lost despite owning the best bullpen in the game, a game they lost despite eight shutout innings from their ace Masahiro Tanaka, was one of the most painful early season losses, and a game that was emblematic of the frustration that defined the first half of 2016.

By game score, this start was actually Tanaka’s best of 2016, and the Yankees still lost. Not great.

August 16th, 2016- New York 6, Toronto 12

At first glance, this game appears uninteresting. The Yankees gave up a dozen runs to a Blue Jays team that can mash. So what?

Well, for one, this game may have been when Gary Sanchez really started introducing himself to the world. He had been up for a week or two prior to this game and had been hitting well, but on August 16th, Sanchez smashed a pair of home runs for his first multi-homer game. Since then, Sanchez has hit .311/.401/.741.

Thanks to Sanchez and five shutout innings from Michael Pineda, the Yankees led 6-0 through five innings, before a rain delay halted the proceedings for nearly an hour. Once the game recommenced, the Blue Jays dropped 12 unanswered runs on the Yankees’ unsuspecting bullpen.

No one could get an out, it seemed. Anthony Swarzak gave up four runs, which isn’t surprising, but Adam Warren also surrendered a four spot, which is surprising. Those were the first runs Warren had allowed all year since returning to New York. Chasen Shreve came on to allow four runs of his own without retiring a single batter.

Before the rains came, the Yankees had a 97% win probability according to Baseball-Reference. By the time the ninth inning rolled around, it was Toronto that had a 98% win probability. This game will probably be lost to the sands of time, but the Yankees will rue it as one they simply should have had.

September 15th, 2016- New York 5, Boston 7

And, of course, the most excruciating game of 2016. The Yankees entered this game, the first game of a crucial four game set in Boston, just two back in the Wild Card chase. They still harbored legitimate playoff hopes at this point, but they needed a strong series against their archrivals to stay in the race.

When the Yankees entered the eighth inning of this game with a 5-1 lead, Baseball-Reference assessed their win probability at 97%. Their odds of winning were still 95% even when Dellin Betances was struggling on the mound, with two on and one out in the ninth.

Within moments, those odds dropped to a round zero:

It’s almost impossible to dream of a more haunting scenario. Blowing a three-run, ninth inning lead on the road against the dreaded Red Sox? In the middle of what was at that point still a fairly spirited pennant run? With Betances, the Yankees’ ace reliever on the mound? With the (possible) exception of the 2015 Wild Card game, this was easily the Yankees’ most crushing loss of the past four seasons.

That loss spurred on a Boston sweep of the Yankees (a sweep that included two more games where the Yankees blew a multi-run lead), and a losing streak that put an abrupt end to the Yankees’ playoff chase. This is the game that, above all, the Yankees will surely rue when they reflect on this season. For the most part, this season has been a real positive for New York. But games like this were still painful pills to swallow.