This ownership group has been burnt over and over by free agents and expensive contract extensions. It’s not crazy to see why they’d want to avoid them.
They clearly targeted YY as probably the only guy worth a massive investment in and spending. Not just the Sox, but most teams don't get the value out of big FA contracts- the success rate on them seems to be pretty low... just thinking of some of them that have came through Boston (both FA's and trade/extended agents)- Beckett, Lowell, Crawford, Gonzalez, Lackey, Ramirez, Pablo, Porcello, Price, Martinez, Sale, etc.... It's really a mixed bag and more likely leaning towards the bad ideas side.
I don't know what the right answer is... and maybe YY was never going to sign, no matter how much the Sox offered in overpay, but if $20M is going to a downtrending Teoscar I just don't see how adding that but just getting B grade pitching really helps.
The OF as currently constructed is probably fine IMO but adding Gray and Nola to the overall team and doing nothing with the OF is significantly a better value, even if you're crazy overpaying for those two, rather than losing out by 2M per season on those guys and then getting Hernandez, then getting some value starters (say Gioloti and Stroman) and Hernandez.
Just wondering basically is $60M spent on Giolito, Stroman and Teoscar* better value than $60M spent on Gray and Nola? I don't think so.
---And I'm not saying that I know the Sox could have got those two for $30M per season, but I suspect that they could have.
*And I actually think that cluster will end up being more than $60M per