It’s very possible the Sox had no chance of extending Betts. But if that’s the case, then trading him was absolutely the right move, and hindsight only drills this point in even deeper, as the Sox have since lost Sale and ERod.
Dombrowski did a great job acquiring Cabrera, but his extension of him already ranks among the worst contracts in MLB history, and it’s far from over. His contract with Verlander looked that way, too, but Verlander somehow jumped back atop his game after a couple years where it looked like he was declining into mediocrity and is back among the best starters in MLB. Maybe the mistake there was unloading him, but I can totally understand why he did it.
He did have a weird knack for not only ignoring closers in Detroit, but the bullpen in general. He appeared to switch this philosophy in Boston not only with Kimbrel but also in his early deals to acquire Tyler Thornburg and Carson Smith, both of whom flopped for reasons unrelated to Dombrowski (unless he ignored medicals?).
The Sale extension was the most perplexing. I think everyone in the Milky Way figures Sale to be in line for a much bigger deal, and it was such a bargain, one could only wonder - were the medicals being ignored? Or did Dombrowski figure even if Sale missed some time, the overall contract would still be worth it.
The Eovaldi contract was f***ing stupid. If the rest of MLB was that hot for him, DD should have let him walk. World Series hero or not...