You expect things to go well for the New York Yankees. If hope springs eternal, then envy does also — mostly among the 29 other fan bases. Over the past few years, though, the Yankees have repeatedly run into their own sort of obstacles, and their own form of disappointment.
Their playoff exits under Aaron Boone have been crushing. Their offseason choices under legendary GM Brian Cashman have ranged from the typical Yankees swagger to what some would call a more restrained, holistic approach and others did call half measures. Their expectations have remained the same: Win the World Series.