I think the Sox are going "all in" in their own way. It's just that "all in" to the Sox is not what it is to the fan base, who is happy to spend unlimited amounts of money because it isn't ours.
Hendricks is an all in move.
Lynn is an all-in move, even if we extend him for a couple years.
Eaton is even an all-in move if you don't have the money for Springer because the other OF on the market can't really play RF, and because he's not so expensive you couldn't also get Hendricks.
Kluber would be been the ultimate all-in move if they could have kept him from going to the Yankees, because if he's returned to 2014-2018 form he could top our rotation, and because it would deprive the Yankees of the starting pitching they would need to beat us.
Tony LaRussa was definitely an all-in move, because you don't accept the risk he poses if you don't think his experience can get you to the WS.
I happen to think the Sox are a couple of moves short of being "all-in" for this year, to give themselves the best shot at the playoffs and WS. But I'm not privy to their financials or what they can do.
How much more can the Sox spend to truly be "all-in"? That's the question.
My personal remaining wish list was Kluber, who could be a bigger steal for $11M than Lance Lynn is for $8M. And Michael Brantley, who should be available for less than his $16M salary from the last 2 years. I would give him the $13M we had allocated for Encarnacion's option.
What the Sox shouldn't do is spend money on mediocre pitching just to have another starter. Whomever they look to add needs to be an upgrade over the alternative.
For example, if the Sox are going to sign a DH/LF or DH who plays some other position, they need to be a solid upgrade over Vaughn's rookie year.
Similarly, if the Sox are going to spend real money to sign another starting pitcher, they need to be a solid upgrade over Cease/Kopech/Lopez when you factor in the potential improvements those pitchers might make under our new pitching coach. They really should be someone you would consider starting in a playoff game.
At this point, with Kluber gone and Bauer being the only FA pitcher left who would give us a World Series boost, I would probably focus on adding a bat like Brantley's, because that would give us the biggest upgrade.