The New York Yankees have been eliminated from postseason contention. Somehow, I have managed to avoid raging enough to eliminate my column from October in response.
Still, I would rather do anything in the world than think about the Yankees’ postseason performance — the very little that went right, the mountain of things that went wrong and everything in between. I would even rather do math.
One of the most offensive things about the Yankees in their last few years of mediocrity has been their mindset. As former captain Derek Jeter said, “It doesn’t matter what you do during a 162 game schedule. It all boils down to the World Series. Win a championship or it’s a failure.”
Win a championship or it’s a failure. Period. End of sentence. Every year my October has been cut short in the last sixteen, a well-meaning friend will try to cheer me up: “But they did so well!”
No, they didn’t. There is no “did so well” — there is a World Series, or there is a failure of a season. If Jeter believes that, then so do I.
But the people who matter do not define success in this way.
After the Yankees slinked lifelessly out of the 2025 postseason, manager Aaron Boone delivered a post-mortem press conference. What should have been an introspective eulogy sounded more like a half-hearted excuse: the Yankees, said Boone, “are working our tails off to put us in the best position to take our shot every year and take a run in October.”
“I’m confident in our organization to build a team that gives us a chance to win,” Boone said.
Boone’s message is clear. No longer is it the expectation to win the World Series. The expectation is to have “a chance.”
But even if we accept Boone’s flawed assumption that once a team earns a spot in the postseason it can only watch as fate rolls the dice, we still cannot fully explain the Yankees’ sixteen consecutive years of falling short. If the postseason is a crapshoot, the Yankees defy the odds.
I wasn’t lying when I told you I would rather do math than relive the Yankees’ October. Han Solo said “never tell me the odds” — but since you are not Han Solo, I will, in fact, tell you the odds.
The Odds
In the sixteen years since the Yankees’ last championship in 2009, they have made the playoffs twelve times. Twelve pats on the back for Boone and his predecessor, Joe Girardi. In six of those seasons, the Yankees either won the division or earned an automatic wild card bid into the American League Division Series (ALDS): 2010, 2011, 2012, 2019, 2022 and 2024. In the other six, they were subject to a wild card game or series before the ALDS began: 2015, 2017, 2018, 2020, 2021 and 2025.
A team that earns a direct bid into the ALDS must win three series in order to win a championship ring: the ALDS, the American League Championship Series (ALCS) and the World Series. A wild card team must win four — adding in the best-of-three wild card series.
Therefore, the Yankees needed to win three consecutive series six times and four consecutive series six times. Assume, as Boone does, that a series is nothing more than a coin flip — each team has a 50% chance of advancing. The odds of winning four consecutive series then is (0.5)4, or 0.0625. The odds of winning three consecutive series is (0.5)3, or 0.125. Multiplying the inverse of each postseason’s probability together results in the following not-too-messy half of an equation: (0.9375)6 ⋅ (0.875)6.
The result? 0.3047. Translated into English, the probability that the Yankees did not win a World Series in the last sixteen years — under Boone’s crapshoot model — is 30.47%. In 69.53% of these simulations, they would have won at least one World Series by now.
Perhaps the Yankees should look into whether the dice are weighed against them. Maybe it is their defeatist, “everything is out of our hands” mindset that tilts the odds out of their favor.
Attitudes trickle down — and Boone’s might just be poisonous.
