The Red Sox became what they hated, the Evil Empire NYY that overpaid for stars. Drew made $10+ million per year and got very few hits that mattered.
They wrote bad contracts, probably bidding against themselves for Crawford ($142 million), a bust so far, with six years left. Lackey is a complete bust. Dice K was the luckiest RS pitcher in 50 years, until his luck ran out. He had unreal run support for two years.
They do have a lot of recent home grown success that was rare before Theo got there. The bad contracts were probably not all Theo's fault. There were (are) plenty of chefs in the kitchen with Larry Lucchino, Tom Warner and the owner John Henry.
There is a limited shelf life for GM's and field managers in Boston, with sooo much pressure to win. The town cares so much.