The big issue with the Mookie trade was the limited interest, which was probably influenced by the inclusion of Price. The Sox had two offers, and the San Diego one was even weaker (plus they wanted Boston to take back Wil Myers, which made zero sense since he was owed nearly as much as Price).
No one chanted “keep Brusdar Graterol” louder than I did. But he really didn’t turn out to be any more useful than Wong plus Downs, did he?
I heard stories Bloom originally wanted Will Smith, but no idea.
Whether or not Friedman planned to extend Betts is immaterial. If the Sox didn’t trade him, he was only under contract for one season. If the Sox didn’t trade Betts, they weren’t going to have him for 13 years. More likely he leaves after one and then signs with LA for 12 years anyway…