Carl Crawford was literally one of the best players in baseball the year before the Sox signed him. It's really kind of nuts how terrible he became immediately, and arguing that it was a bad signing the minute he signed is silly.no way. All of those signings were bad the minute they were signed. What was the upside of Sandoval, a 2.5 WAR player that wasn't going to age gracefully? Castillo might have amounted to Ellsbury without the speed (which is to say, at best a league average player)? All of those contracts were garbage. Sale is at least a good pitcher if the contract works. The contract didn't work. But he had upside, and they traded Kopech and Moncada for him, so it made sense.
Those signings were all like the exact opposite of what a reasonable FO does