DD signed JD for half of what his agent wanted, Bogie to a team-friendly deal, Eovaldi at market value for a near-top of the rotation starter, and Pearce for what amounted to a $6 mil bonus for winning World Series MVP (budget damage was similar to the $8 mil that kicked in for Schilling for his final season he sat out injured). He also let Kimbrel walk -- who was then paid, instead, by ex-Red Sox front office boy wonders in the NL.
Besides the Price albatross, DD's Beantown legacy was smeared by his last big move, locking up Sale before he could prove he wasn't damaged goods (he couldn't, but imagine if the Sox hadn't extended Sale and then he won the Cy Young in 2019 and became a free agent?). Sale missed the 60-game Covid season, and half of this one, but obviously still has time to recover and make good on the second half of his contract. If Sale becomes an All-Star again, does Dombrowski's Boston signings really look all that horrible in retrospect?