I know it's pretty ridiculous - and he likely (smartly) take the best money he gets, but man, his legacy would super weird if he signed with like the freaking White Sox. At least Philadelphia or St. Louis would be a good situation as long as he's got nearly identical money to Chicago.
If I was a player and had my choice and was looking at $300+ million guaranteed, I'd be really careful about where I sign. Like if he goes to CWS...how is he even relevant anymore?