Here's the problem with signing or not signing the high priced FA's. The FO has dual goals. Goal #1 is to make money and goal #2 is to win. As a short term solution signing the FA's solves goal #1. If the fans think the Sox are going to be winners they'll come to the park and spend the money. However, it may not be a good long term solution because if these FA's don't play up to their contracts the FO is stuck with those contracts - and as Moon has pointed out, most FA's don't.
OTOH, if they don't sign the FA's much of the fan base will think the Sox aren't trying to win and they'll stop showing up at the park, especially if the team gets off to a slow start. Which costs the organization a lot of money. Right now the FO is trying to lure fans in after two straight last place finishes by not raising ticket prices and making promises that the team will be better.
It's still working, but for how long?
Those two goals aren't mutually exclusive. There's more money in winning than there is in losing, by far.
BTW, watching the Olympics & the men's 100M backstroke. A great quote from one of the announcers after Murphy won the gold and the US won the gold for the sixth consecutive time. "Welcome to the club my friends''......... for the show that never ends!
GO USA!