When he was hired, Dombrowski was the right guy for the organization but it was time to move on and hire a guy who would build a better foundation for the future.
Dombrowski is like that high-priced free agent pitcher--he will help you win in the short term, will make you better in the short term, but his long term impact is less certain.
Henry made a brilliant decision in hiring Dombrowski. Dombrowski delivered a championship, the architect behind the 2018 Red Sox, one of the best teams in the history of MLB. In contrast, just think how lousy Yankees fans feel. Cashman has been a total failure over the last decade and has no clue on how to put the final pieces in place to win the World Series. The Yankees should move on from Cashman, but they are led by dumb ownership--the Steinbreener kids, the ultimate welfare recipients.
I'll always have a soft spot for Dombrowski. The 2018 regular season and playoffs were the most enjoyable to watch from start to finish. True, nothing beats 2004, but 2018 was less anxiety-filled, and more smooth sailing. The 2018 team kicked everyone's ass (no game sevens in the playoffs, for example) and that kind of team was so fun to watch.