This is what actually matters: of the top 20 highest paid players in baseball, 6 are on a different team than the one they initially signed the contract with. Of the 6 teams that initially signed them, the Sox (David Price contract) are the only one with a chance to make the postseason. Of the other 14 highest paid, 8 are on non playoff teams, and one (Bauer) is potentially out of the league. So of the 20 players with the biggest contracts this season, a total of 5 are potentially playing in the postseason with the team that signed the massive deal. Those 5 are Cole, Altuve, Verlander, Kershaw, and Goldschmidt.
This really speaks to the fact that signing players to massive contracts is not a way to successfully build a team. Mookie is 45th in MLB in fWAR this season among position players, and would be 4th on Boston. His 3.8 fWAR is his lowest ever other than his 52 game 2014 and his 55 game 2020. Fangraphs has his defensive contribution as negative for the first time in his career. He’s old enough that it extremely likely that he’s last his prime defensively, and if his defense isn’t elite, then neither is he. I still think he’s a great player, but that contract will be an albatross, and anyone still upset we didn’t give it to him is being willfully ignorant