The Red Sox picked up Jon Lester's $13 million option for 2014, keeping him around for at least one more year. Both sides would like to work out an extension to secure Lester in Boston for years to come, but it's not going to happen for some time yet, according to Rob Bradford. Spring training is looking like the starting point for those discussions, with both Lester and the Red Sox taking the winter off on this conversation.
Why the lack of urgency? If the Red Sox wait to unveil an extension until after Opening Day, they can retain the benefit of Lester's $9.4 million average annual value for 2014, giving them more room to play with under the luxury tax, or, at the least, less money over the tax threshold, should they end up in that predicament. If they were to sign Lester to a deal with a loftier AAV -- and his next contract will tower over his previous five-year, $30 million one -- they would lose that, and have less flexibility to work with for next year.
This is similar to the timing of the extension for Adrian Gonzalez, whom the Red Sox traded for prior to 2011 with every intention of signing long-term. The extension was not announced until after the regular season had begun, but there were whispers almost immediately following the deal that something was in place, just not officially signed, in order to maintain the benefit of his insanely affordable $6.2 million club option for 2011. The Sox and Lester might similarly work in secret on an extension before spring begins, but whether they figure something out sooner or later, it won't be announced or official until after Opening Day.
FOX Sports' Ken Rosenthal reported last month that Lester's next deal could be anywhere from $146 million in value to over $200 million. The latter is unlikely, unless Lester pitches the entirety of 2014 before signing a deal, and is one of the game's best pitchers while doing it, but $146 million is not out of the realm of possibility should the Red Sox -- or Lester -- let negotiations linger through the year. Given the price of pitching on the free agent market -- this is a world where Ervin Santana could very well end up with a five-year deal for $75 million or more -- Lester could end up signing for something that looks silly on the surface, but is, in fact, relatively safe compared to the frightening prospect of bringing in expensive outside help for the rotation.