Via Jon Heyman: Along with the Cubs, the Yankees are viewed as a likely landing spot for free agent-to-be left-hander Jon Lester this offseason. Heyman says a reunion with the Red Sox is considered unlikely. The Cubbies are run by Theo Epstein and Jed Hoyer, who obviously know the southpaw from their time in Boston.
Lester is a great fit for the Yankees because he’s a great fit for every team in baseball. Every club could use a prime-aged workhorse left-hander with proven big market and postseason chops. The real question is whether the Yankees are willing to take on a third $20M+ annual salary pitcher, especially given the other holes on the roster. The team is very top heavy and I think they need to focus on adding several solid players rather than one star plus a bunch of replacement level guys this winter.