Brian Cashman? Granted he's always had a financial advantage to bring in the big contracts (free agent or trade), but it's not like the Yankees haven't had a relatively steady flow of younger players over the years.My question is - surely there are folks out there who can play both parts: builder and GFIN-er in turn, when appropriate? Who can balance how they attack roster building and trades? Do you gotta be a Cherington OR a Dombrowski? Theo certainly seemed to have that balance. Maybe Bloom does, too, indicated by the Story signing (let's see if he uses a chip or two to improve the pitching) ...
I think there are plenty of guys who can "play both parts" and it really shouldn't be an either/or question. The problem is owners often get too impatient and don't let guys finish the job one way or the other. Cherington might be someone who can do both (2013 suggests that) but he got pressured to make some rash decisions before his farm work had fully been realized and then got replaced by a "proven" GFIN type who obviously pressed all the right buttons to win in 2018.