The front office's expectations have always been unreasonable. It's unreasonable to expect to win a championship every year.
Yes, the Yankees are set up pretty nicely for the playoffs, all things considered, but there have been numerous instances in the past decade where the best team did not win. That doesn't mean it was a complete failure each time.
Think about it this way. Everything about baseball is built on the idea that things even out. Over a small sample size flukes often occur, mainly because there are so many variables involved in the outcome of a single baseball game. The Yankees lost their first series this season to the Baltimore Orioles, a team they are significantly better than. Was that an utter disaster? No. Was that a cause for concern? No. Why? Because, in baseball, things tend to even out over a larger sample size.
Mark Teixeira got off to a poor start this year. Was it a concern? No. Why? Because things tend to even out over a larger sample size. How's Mark Teixeira doing now?
I was very upset about the ball four that was called to Nick Green the other night, which allowed the Red Sox to tie the game. While most Red Sox fans on this site acknowledged that it was a bad call, I received many responses saying that those things tend to even out over the season. Sure, the Red Sox got a call that gave them the game, but there were probably calls that cost them a game also. It's a long season, and they're absolutely right, things do to tend to even out. However, in a short playoff series, they don't. Did the Cardinals ever get retribution for Don Denkinger's call? Did the Orioles ever get retribution for Richie Garcia's call? Did the Red Sox ever get retribution for the blind tag on Offerman? No, because it was over a much smaller sample size.
Nobody even blinks an eye over Lonnie Smith's poor base running if the it's during the regular season. Sure, he got fooled by Chuck Knoblauch, but it could happen to anyone. However, in the World Series, that one base running mistake cost the Braves their season. When one tiny thing going wrong can cost a team their season, how is it not a crapshoot?
I'll give you an example that involves the Yankees. The Yankees lost the 2002 ALDS mainly because after being staked to an early five run lead in game 3 (series tied 1-1) Mike Mussina injured his groin. If that doesn't happen the Yankees very likely win that game, and go on to win the series. Instead, even though they were the superior team, they lost, and the Angels went on to win the World Series. It's those minor things that are relatively inconsequential over a large sample size, that can end your season over a smaller sample size (the playoffs).