Show them the money and see how fast that perception changesFair, and a couple of reasons:
1 - Each of the GMs that inked those deals had won a(t least one world series), so I trust them more. What can I say. I'm a sucker for a World Series title giving some cachet.
2- Because I think there is a large difference between betting on a 26 year old whom has shown an ability to produce in Boston as opposed to Crawford (29), Gonzalez (29), Ramirez (31), Sandoval (28), Price (30), JD Martinez (30) whom hadn't.
2a - Sale, started to show signs of breaking down in 2018 when he missed 5 (or 6) turns through the rotation and was then pretty awful in the playoffs. He was going to be 30 when the extension started and doesn't have a body type or delivery that one would bank on. That said, I liked the Price singing (not the Sale extension) so call those a "wash", if you will.
3 - Because I think you need core pieces, the only one we have is Trevor Story and I'd like Devers to be a second. To my point above, I think you need top of the roster talent to win a world series. Sure, the Royals managed without any in 2014. But the Rays / As model has gotten beat in the playoffs before raising a flag each time. To reiterate, though it happened once (KC) I think it's almost impossible to win a World Series without high end roster talent, and the only one we have right now that is even a moderately safe bet to play a full season effectively is Trevor Story.
4 - This in conjecture, but I don't think Boston is seen in a positive light at all right now by young MLB players or the industry in general, and I'd like to change that.