His tactic for winning works short term and fails long term, which it did in both Miami and, to a lesser extent, Detroit. In Boston, he did leave the team in a bad place with no farm to support a slew of hefty contracts.
Winning is easier when your owner lets you spend a lot. Give Dombrowski the same constraints Cherington had and the 2018 Red Sox season might have been very differen.
And by “to a lesser extent”, I meant the winning in Detroit. The aftermath was actually quite devastating. Still is, in fact…