Lester has made it clear that no matter what happens during the trade deadline season, his top priority is to return to Boston at the end of the year. That should be the cue for Cherington to go ahead and deal the hurler, but as we all know, nothing goes as planned for a baseball team. But Lester returning to the Red Sox seems like it could actually happen.
Lester has been a member of the Boston Red Sox his entire career. They drafted him back in 2002, and have already agreed to one extension with him, signing a six-year, $42.75 million deal that started in 2009. Lester has won two World Series championships with the Red Sox in 2007 and 2013. He's a homegrown Red Sox talent, and there is no reason to believe as to why he should go elsewhere when he becomes a free agent.
Cherington would likely get a pretty good deal for Lester, regardless if the team that acquires him believes that he is going to stay after this season or not. When you look at the stats, Lester is one of the best pitchers in baseball, and next to David Price and Cliff Lee, he could be the biggest trade target of the trade deadline.
On the season, the 30-year-old Tacoma, Washington native is 10-7 with a 2.52 ERA and a 2.62 FIP (Fielding Independent Pitching) in 143 innings pitched. His 155 ERA+ suggests that his ERA is 55% percent better than the average pitcher. He will net the Red Sox prospects, guaranteed.
The only reason I could see as to why Cherington is skeptical of dealing Lester is if he has such a good time wherever he goes, he could be willing to stay with them or go back to Boston. Then it could become a bidding war. If Boston keeps Lester, then he will not have the feeling of being in another clubhouse, and therefore a re-signing is more likely. However, as a general manager in baseball, almost everything you do has some risk attached, and Cherington has to take this risk.
If that scenario does play out, however, Cherington needs to be satisfied with the prospects he gets. He cannot name a price on Lester and expect teams to line up for him; that just will not happen. These days, teams are less willing to give up their best prospects to get the best talent. He needs to understand what teams are willing to offer, negotiate a deal that works for him, and hope that Lester comes back in the offseason. I strongly believe that will be the case.
Here's an excerpt from an article written by Gordon Edes of ESPNBoston.com about Jon Lester and the Red Sox situation:
"Red Sox ace Jon Lester on Friday night sounded as if he is prepared to be dealt, saying GM Ben Cherington has to do what’s right for the organization and adding that he would bear no hard feelings. Lester said he would consider re-signing with the Sox as a free agent even if they traded him."