Trading John Lackey doesn't make sense for the Red Sox unless they are getting a massive return that they can't turn down. That's what makes Ken Rosenthal's latest a little frightening: there's a "very good chance" the Red Sox actually ship both of Jon Lester and John Lackey out, not as a package deal, but in separate transactions.
Here's the thing: Lester is incredible, one of the best starters in the majors, but he's a rental. He'll be a free agent in two months if the team acquiring him doesn't make the playoffs, and said team might always regret giving away pieces of their future for the lefty if they don't win the World Series. That rental situation would make plenty of teams on the bubble understandably apprehensive about handing over certain prospects to the Red Sox. Swapping in Lackey for Lester for a cost-conscious team who can't be giving up top prospects for straight rentals could result in a profitable deal for the Sox where Lester would have been a non-starter.
Rosenthal says teams in this scenario are the Marlins -- who were also connected to Lester -- and the Indians. Both fit the bill -- well, the Marlins have money, but that's another story -- as clubs with prospects who might not be close enough to risk it on Lester, but could be talked into Lackey.
Losing Lackey would leave an enormous hole in the 2015 rotation for the Red Sox, as they would have Clay Buchholz, maybe another shot with Felix Doubront, and then all prospects and current rookies for the rest. Brandon Workman, Rubby De La Rosa, Anthony Ranaudo, Allen Webster, and eventually Henry Owens all have talent and real potential, but relying on them heavily in 2015 could be a sign that next year is a purposeful bridge, instead of an accidental one like 2014. Let's not get ahead of ourselves, though: the Red Sox could simply be shipping Lester and Lackey out to get something(s) the system doesn't have at present -- impact, up-the-middle prospects -- to join Xander Bogaerts in crew in the coming new-look Sox, all before making another trade with their depth elsewhere to fix the rotation.
That's kind of the thing we need to remember in general as this deadline approaches: the Red Sox are making moves for 2015 and beyond, but it might take until we're into 2015 to see things come together. Patience, y'all.