YY was the move to make in the same general sense that asking out the hottest and most popular girl in the school is for Joe Average with absolutely no standout qualities going for them. Regardless of the fact she already has dreamy eyes for Johnny QB, and who by all accounts really likes her back. I mean Johnny QB may be better looking then you are, is a lot more popular, drives the better car, and (polar opposite to you) has every other girl in the school crushing on him too. But hey...you never know right? Which on that note was basically my takeaway summary from sitting down to read the first 35 pages of this thread the other day, and now the couple pages that popped up today after the Giolito signing. 90% of what I'm reading stikes me as the equivilent of Joe Average and his buddies fantasizing out their top 5 hottest-girls-in-the-school lists, and while essentially detaching themselves completely from the underlying reality aspect in play that none those most ideal/in-demand girls actually think you are cute. Much less look at you the same way you are looking at them.
The surrounding landscape and off field consideration values have changed a lot even in the last 5 years. If you made a list today of the top 15 most attractive MLB team destinations for players at face value....does Boston even realistically make it on there? As my diehard 40 year Jays fan brother likes to constantly remind me nowadays, at some point you have to adjust the lens to account for that changing reality. Especially when it comes to the expecations that go into trying to "win" in free agency. Boston can't even slap down it's once bread-and-butter "come here for a chance to win" appeal card anymore. Yet you actually think WE get to sign a FA like Montogomery to a market value type deal in a competive offer field? Sorry, but no. That just isn't how it works on the other side of the comparative appeal coin we now reside on. For THIS team today getting a FA to take your money over somebody else's equal'ish value one elsewhere isn't some minor consideration hurdle in the overall equation anymore.
Breslow went into this winter with zero shot at being the winning bid on YY, and while staring down a liklihood that even those next couple of best options like Montgomey/Snell/ect were going to realistically take a Padres' level of overpay on backend years to trump the competive field. That is how you end up where we got yesterday with that Giolito signing, and where more of the unacknowledged value can be found in that signing. Boston will simply never be a great comparative desination sell at face value. To start "winning" again in today's free agency we need to get back to the point where we can at least start offering players a better chance to win ballgames then they hopefully can/would find in less of the other competive offers out there. With next year hopefully being a step forward in that regard.