Who cares if he becomes a Yank? They like any other team signing him are probably getting 2 good years and ?'s anything after that. CC fell off a cliff. Could happen to Lester. I would find a useless CC and a declining Lester clogging up the Yanks rotation funny. Ya maybe he goes there and is aces for 6 or 7 years, in today's game I don't see it happening. If the Sox signed him to 6 or 7 years I would not be excited at all.
If they decide to see everyone not named Pedey, Papi, Xander, and Napoli on the ML roster should be available imo. Lester, Lackey, Koji, AJ, Ross, and Drew could net a huge overall haul of prospects. The Sox farm system would be absolutely bursting with top 100 talent. They could make a big trade in the off season or use that talent in a Sox uniform. I think watching a young group come up around Pedey, Ortiz, Xander, and Napoli.