I think this speaks to a few things
1) The cubans recently have nearly all outperformed expectations, to some extent that's going to help access future players. All the recent cuban deals look great value
2) It's getting ever harder to use money to acquire talent. The draft is now controlled and an IFA draft basically appears a done deal at some point. The smarter teams all en mass just blew up the IFA pools in a nothing special year of talent. Guys who wouldn't have got much under the old system got top dollars. This despite penalties for overspending too!
3) Pitching is ruling hitting in the majors at the moment, the bar for a good defensive player with speed is a lot lower than it was a few years ago. I mean look at JBJ, his defense alone (as he's not quick) is nearly offsetting one of the worst stat lines in modern history.
4) Money is flooding the game, AND teams are getting smarter at locking up young talent.
5) The sox have a lot of low pay players on the roster. The worst case for this year on a per year basis is unlikely to hurt the organization a whole lot in the near future. (Vasquez, Xander, Betts, JBJ, Kelly, RDLR, Webster and so on are all playing for minimal money and Pedey, Napoli, Cespedes, Napoli, Shane and Papi are all well off top money and/ or are on short years). This is a sweet spot to take this kind of risk.
I don't know if this guy will work out, but if he can play CF and has real speed the bar of hitting to justify the contract is low.
I'm very confused how all the pieces fit, but there is a whole offseason plus to change that, so I'm willing to be patient.
As someone mentioned I ever more confused on the craig move. Some are suggesting Craig had negative value, which I don't get at all. And if he was negative value then the LAckey for Kelly minus trade looks bizarre and maybe horrible. Picking up money to downgrade from lackey to kelly just seems weird. Maybe the team is super high on Kelly, but eh.
Assuming that line of thinking is incorrect, then they had a plan for Craig. They already had JBJ and Betts and Shane and Nava and Cespedes and Stanton. Oh wait that's not real. 1B has Napoli and DH has Papi. Craig can't really play RF IMO so he's for LF if he's playing everyday next year. The year after fine a lot of options.
Edit: btw the Yanks just discovered they could use money to acquire ALL the IFA talent. The fact they haven't been in on the cubans is mind boggling. In this specific case I think it makes sense (as they have a number of similar players already), but how they weren't in on some of the others is just... well good but bizarre.