2.) Philadelphia Phillies
The Philadelphia Phillies are up next and this is an interesting one because Dave Dombrowski has a strong track record of success as an executive but with some caveats. Ever aggressive in his pursuit of stars, Dombrowski has routinely put together strong rosters in all of his stops in his career, but it has often been at the cost of his teams' prospect pipeline as he has left more than one organization bereft of minor league talent.
Dombrowski has remained the same sort of guy in Philadelphia as he extended JT Realmuto, signed Trea Turner to a mega-deal last offseason, and have added Nick Castellanos and Kyle Schwarber as well during his tenure atop the Phillies front office. The end result was a surprising run to the World Series last season and it looks like they will be playoff bound again in 2023 barring a collapse. One fully expects that the Phillies will remain in the mix at the top of the free agent and trade markets yet again this offseason.
Dombrowski is definitely the kind of guy you want around when an owner has deep pockets like John Middleton, but there are some flaws here. Dombrowski sees prospects as trade chips and given that, it is going to be hard for the Phillies to develop cheap, talented players to fill roster spots. That can work for a little while, but it isn't particularly sustainable especially when you look at the lack of depth in the Phillies' farm system thanks to some lackluster draft classes, injuries, and failures in player development.
Has Dombrowski helped make the Phillies a good baseball team? Yes, without question. Will they remain a good baseball team who is aggressive over the next couple of years under Dombrowski? Almost certainly. However, as Bryce Harper, JT Realmuto, Zach Wheeler, and Aaron Nola get older and inevitably start to decline, it is hard not to think that Dombrowski will see the writing on the wall and move on to his next short-term project because, well, that is just what he does.