Wow, this is a remarkably awful summation of his career, not to mention probably the worst metric by which to judge an executive's performance.
In Montreal, as farm director and GM, he helped lay the foundation for the 1994 Expos, who had the best record in baseball at the time of the strike, was loaded with top end players and would likely have done quite well in the playoffs. The strike killed baseball in Montreal (in part) and soon the team had to be dismantled, so we don't know how far they could have made it, but that was an amazing group of talent.
He moved to Florida in 1992 to helm an expansion franchise. By 1997 they won a WS, with the following players acquired by DD: Kevin Brown, Moises Alou, Bobby Bonilla, Al Liter, Livan Hernandez, Edgar Renteria, Louis Castillo, Gary Sheffield, Jeff Co -...wait let me just link the team page
(
https://en.wikipedia.org/wiki/1997_Florida_Marlins_season#Roster) considering he
literally built the entire team and organization from nothing and won a WS in the span of 5 years and another shortly after that. He was then told to blow it up. The moves he made blowing it up set the team up to do the same thing and win it again six years later (Mike Lowell, AJ Burnett, Matt Clement, Derek Lee, Brad Penny, etc).
He went to Detroit in 2003, when they were coming of a season losing 119 games. That's not a typo, they were literally the second worst team in ML history edging the '62 Mets by one game. He had that team back in the World Series in three years. The players he acquired via different routes during his tenure in Detroit are too long to list (you can see them here if you'd like
http://www.baseball-reference.com/bullpen/Dave_Dombrowski), but his Tigers teams went to 2 WS, 2 other ALCS and the playoffs a fifth time, with four consecutive division titles in the process.
He was hired to do exactly what he has done in his career and what Henry wanted - turn a team around quickly and set them up for a long run. He was the best man for the job.