I know I'm somewhat of a DD apologist, but he inherited a team with no pitching and not a huge amount of payroll room thanks to the Pablo/Hanley contracts. So he had little choice to trade prospects for pitching, as far as I can see.
The team wins 93, 93, and starts this year 25-9.
He can't have done all that badly with his moves so far.
The future might be a different story, of course.