I get the "last man standing" point, and the enormous pressure JH was under to not let that "last man" bolt, but the fact is he did it- hand pried or otherwise. $300M/10 was not something to just waive off as an anomaly.
Trading him, not long afterwards, seemed shocking, at the time, but in the grand scheme (or should I say sham) of things, he undid what he was "pried" into doing. I do think it was more him than Brez that made it happen, but it could have been Brez's suggestion.
We've certainly made enormous strides with extending our own players- homegrown (Anthony, Bello, Rafaela & Campbell) and not (Crochet.) That's a great sign that things are changing on the financial side of the organization. It took a long time to wake up, but I think that might have had something to do with their previous record actually being pretty good on knowing when to let some key stars go. They had missed on a few (DLowe, Beltre and the biggies, Lester & Betts) but others were more nuanced (Damon, Manny, Bogey and others) or downright great moves (Ellsbury, Pedro, JD, CC & Agonand others)
To me, this winter should be the strategic time to buck the trend and go large and long on a big bat. While the ones available have some flaws, the time is now. Schwarber (age and DH only) and Alonso (awful 1B D and a logjam at DH) are the tow big prizes. Settling on two from the next tier might be enough, but that would be two large and long deals after going almost a decade with none. Suarez might not need the "long" part, so he could be paired with Bregman, Polanco or Bichette, or we could trade for K Marte or some other bopper.