After signing Andrew Miller and trading for Didi Gregorius, the Yankees have remained quiet in the few days following. When the Yankees are quiet, it's usually the sign that something big is about to happen, and now Jon Lester is said to be nearing a decision on where he wants to sign long-term. The Yankees have hardly been connected to Lester at all during the offseason, but that doesn't mean they aren't in on the left-hander.
I just had a front office person tell me, "Don't count out the #yankees with Jon Lester.'' Scout hearing the same thing.— Jerry Crasnick (@jcrasnick) December 9, 2014
It has been stated that Lester is deciding between the Giants and the Cubs, though there is no indication about the Red Sox, or really any other team, being out of the running. As these things tend to go, expect some kind of surprise before this is all said and done. According to Buster Olney, Lester is supposed to make a decision either tonight or tomorrow, so we'll see.
The Yankees, of course, have at least two holes in their rotation for starting pitchers. They have Masahiro Tanaka, Michael Pineda, and possibly CC Sabathia, but after that it gets very muddy. Shane Greene is gone, so they wouldn't have much in the way of MLB-tested talent. They could end up adding two free agent starters to fill out the rotation, likely either Lester or Max Scherzer, as well as Brandon McCarthy. Many prefer Lester over Scherzer due to the fact that Lester does not require draft compensation to sign.
After the signing of Miller, the addition of Lester could signal a return to spending that the Yankees have enjoyed before the 2009 and 2014 seasons. Once Lester has signed, the dominoes for the pitching market, and perhaps everyone else will start to fall. If the Yankees end up with Lester, it could mean Chase Headley and David Robertson aren't too far behind.