Jon Lester has been flying around the country to meet with teams interested in his services for the next six years or so, but he won't be doing it for much longer if recent reports are any indication. According to Andy Martino at the NY Daily News, the teams who are chasing Lester expect him to make a decision about his new home as soon as this week, before the Winter Meetings even kick off in San Diego on December 8.
Lester has already met with the Red Sox, Cubs, and Braves, and is meeting with the Giants in San Francisco on Monday. The Cubs have the resources to get Lester, but it's unclear if they are willing to commit them or if Lester is willing to sign up for what end up being yet another failed rebuild in a long line of them in Chicago. The Giants absolutely have the money and the need for Lester, and have the competitive environment he's used to playing in as well. The Braves are considered "longshots" by Martino, but you didn't necessarily need him to tell you that: their interest in Lester is obvious given he's Jon Lester, but Lester mostly seemed to be checking in with them given he lives outside Atlanta these days.
Martino spoke with one executive whose team is trying to acquire Lester, and they believed that "if the right situation presents itself, [Lester] will strike." That feeling does not seem to be exclusive to this one exec.
There is a feeling among officials involved in talks for Lester that the pitcher, soon to complete his information-gathering process -- he is meeting with San Francisco today, ESPN's Buster Olney reports, and has been engaged with at least the Red Sox, Cubs and Braves -- will move toward a decision over the next few days.
No one dealing with Lester and agents Seth and Sam Levinson believes that he has or will set a deadline, but there is a feeling among interested teams that he could reach a decision this week.
It's possible the Giants are the last team Lester plans to visit with, and that once he has an offer from them, he'll make a decision. Martino does say that there is still that whole issue of whether the Yankees will be involved or not to consider, but that it has become "hard to imagine" this is the case. They could always jump in at the very last moment with a lucrative offer that could entice him to come to New York, but all indications so far have been that the Red Sox, Cubs, or Giants are his likely next home.
Regardless of where he ends up, the next steps in the Red Sox' offseason won't be taken until the Lester situation is resolved. If he's signed elsewhere, then talks will likely intensify with the Phillies for Cole Hamels. If he does come back to Boston, then they can work on bringing in a solid number two starter to line up behind him and finish filling out the Opening Day iteration of the 2015 rotation. It's a little difficult to move the trade chips they have until they know precisely what they will need to get with them, but it doesn't sound like anyone is going to have to wait much longer.