As Yookeroo notes, they do win pretty much every year. How many times have the Yankees missed the playoffs since the mid-1990s? Exactly once.
The playoffs are a crapshoot. It’s very easy for a five- and even a seven-game series to turn on a bit of luck, or an outstanding performance by one or two players. The results of the short series aren’t a good measure of a team’s overall quality. Billy Beane understands that; as he said to Michael Lewis, “My shit doesn’t work in the playoffs.” There’s too much luck.
The measure of a good team is a team that does well over a long season, where the overall quality of the team is able to overshadow the day-to-day vagaries of luck. Luck evens out over time, and the good teams rise to the top and make the playoffs.
Of course, you know all this. Less than a month ago, you said:
If you recognize that the regular season is a better measure of team quality, and that the playoffs are a crapshoot, you should also recognize that, by the best measure we have, the Yankees do win just about every year.