Yankees Free Agent Target: Jon Lester

Jon Lester had an interesting 2014 season. He began with the Red Sox, where he had been his entire career. However, he was dealt at the towards the trading deadline to the Oakland Athletics for Yoenis Cespedes. The Red Sox have said all along that they intend to sign him again once he became a free agent in the off-season, but as the months wore on, that looks less and less likely. Now that the World Series is over and the off-season is in full swing, many teams are playing the waiting game to see who will be the first big domino to fall.

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Lester had a greatly successful 2014 season. Between the Red Sox and the Athletics, Lester posted a 16-11 record with a 2.46 ERA with 220 strikeouts in 219.2 innings of work. He was extremely consistent with both teams, with a 2.52 ERA with Boston and a 2.35 ERA with Oakland. Lester picked a great time to have, arguably, the best season of his career. In 2012 and 2013, Lester had ERAs of 4.82 and 3.75. There is a lot of confidence with Lester as he enters his age 31 season.

I have written about Lester before in my article on who the Yankees should sign from an analytic standpoint. I mentioned that of the “Big Three” free agent pitchers this season, he would be the best fit for our club and our ballpark. The Yankees need more lefty starters in the rotation to avoid the short porch in right field. Between being a lefty, his ground ball and GIDP percentage, and his high strikeout totals, Lester really should be priority number one if the Yankees decide to spend big money on pitching.

The smart money is on Jon Lester going to the Chicago Cubs. Reuniting with Theo Epstein and now having Joe Maddon as the coach, the Cubs are suddenly a hot free agent destination, especially for Lester. They have a ton of money, and even more great prospects ready to take on the NL Central.

Lester to the Yankees is always possible. There is no doubt that he would be a huge benefit to a team that always seems to have injured pitching. The team cannot put any faith into CC Sabathia ever returning to form again. There are questions about how close Michael Pineda will get to 30 starts. He showed brilliance last year when he wasn’t hurt. Ivan Nova is coming off Tommy John surgery and of course is not a lock for a full season of pitching. Even Masahiro Tanaka is going to be a question mark because of his partially torn elbow. A guy like Lester should give the team confidence of a full 33 start season from a guy that knows how to handle not just the AL East, but the entire league.

If the Yankees do decide to make a splash on pitching, here’s hoping it’s on Jon Lester.