To me he only seems like a slightly better choice than MacPhail. He didn't win in Boston with players he developed, though he certainly finished off that team. His presence also pretty much chased all the front office talent out of Boston (starting with Cherington and then the D-Backs guys). Detroit may as well be ancient history given the changes in the game. And then he himself got chased out of Boston.
It is also definitely a Gillick-like move, except this club isn't as close as the Phillies were in 2006, and the collapse will come a lot sooner.
But if they are going to win anything at all, even just a division, with Wheeler, Nola, Hoskins, and in Harper and (hopefully) JT"s prime, he's certainly the guy to try and do that. If he has money. Can't be making win-now trades with the farm so thin.
There's a good chance we're already going to be crashed and burned by 2023 without starting to tank/rebuild now no matter what.
Much would seem to depend on what sort of GM he wants to hire, or what sort of GM would work for him. Hard to feel positive about that until proven otherwise.