Jon Lester has been clear about his desire to stay with the Red Sox, as well as his understanding that it will mean he is leaving money on the table. It's tough to believe that sort of thing on the surface sometimes, just given what we know of free agency, that it takes two sides to sign a deal, and whether a player's version of a discount jibes with their team's. According to rival general managers, though, Lester is represented by the right agency to get an extension done, even if it's below-market, according to the Boston Globe's Nick Cafardo.
The Levinson brothers -- Sam and Seth -- founded ACES, an agency that is developing a reputation for "persuading clients to take under-market-value contracts if they're happy where they are." The Red Sox own Dustin Pedroia is one such player, as he signed an eight-year, $110 million extension with Boston that is, average annual value wise, well below market value. He's not alone, though. The Mets inked ACES client David Wright to an eight-year, $138 million deal a year before free agency resulting in a lower AAV than he likely would have received on the open market. Cardinals first baseman and right fielder Allen Craig signed a five-year, $31 million extension with an option that bought out all of his arbitration seasons as well as a couple of free agent years. Rangers starter Matt Harrison similarly signed a five-year, $55 million deal with an option for 2018 that guaranteed his remaining arbitration seasons and tacked on more years of Texas' control.
Lester could very well be the next of these, and might snugly fit in between the Pedroia and Wright contracts in terms of total money. Given what even mid-level starting pitching is going for on the open market these days, either a long-term deal with a low average annual value (a la Pedroia) or a shorter (read: five-year -- context matters) contract with a still-discounted AAV would work well for the Sox and the closest thing they have to an ace in Lester.
Any extension is unlikely to be signed before the regular season begins, as a contract extension would change Boston's luxury tax commitments for 2014. As they are currently contributing less towards the luxury tax (about $9.3 million, according to Alex Speier's calculations) than they are actually paying him ($13 million), it would be silly to announce anything during a time when the 2014 advantage would vanish. Once the season begins, though, an extension beginning in 2015 could be announced, with 2014's terms remaining unchanged.
Per Cafardo, Boston and the Levinsons have already had a pair of conversations about an extension. Knowing they've met multiple times this early in the spring, when no deal is imminent (or publicly imminent) for another month, makes this reported belief of the rest of the league seem more real. We'll just have to wait and see, of course, but if you forced me to bet, it would be on Lester staying in Boston.