Jon Lester finished fourth in AL Cy Young voting. (Getty Images)

Devil in the details: Contract possibilities for Jon Lester and the Red Sox

November 19, 2014 - 9:52 am

The Red Sox have made no secret of their desire to make a push for Jon Lester, a notion that has gained further credence with the reports (the first one of which came from that the team has made an offer to the left-hander. But, of course, it is one thing to make an offer, another to find common ground to satisfy Lester's interest in a salary befitting his status as an elite pitcher and the Sox' interests in accounting for the risks associated with a long-term deal for a pitcher in his 30s. In the absence of concrete details about what shape that offer has taken, here are a few potential models and/or features of an offer that the Sox may try to incorporate as they attempt to reacquire an elite pitcher while minimizing the risk on the back end of the deal: Model 1: Cliff Lee (fewer years, more dollars) In the 2012-13 offseason, the Red Sox proved aggressive in terms of the average annual value they put on the table while trying to limit the number of years they committed to players. In doing so, they got (for instance) Shane Victorino to pass on a four-year deal worth roughly $11 million a year from the Indians in favor of a three-year, $39 million deal to come to Boston. In the winter following the 2010 season, left-hander Cliff Lee walked away from potential deals of six-plus years (with offers typically rumored to be for $23 million or so per year) in favor of a five-year, $120 million deal ($24 million per year) with the Phillies. It's worth noting that there are similarities between Lester's situation and Lee's. Model 2: Cole Hamels and Zack Greinke (market value) Pitcher 1: 1,596 innings - 116-67, 3.58 ERA, 121 ERA+, 8.2 K/9, 3.1 BB/9 Pitcher 2: 1,492 innings - 91-78, 3.77 ERA, 114 ERA+, 8.0 K/9, 2.3 BB/9 Pitcher 3: 1,376 2/3 innings - 91-60, 3.34 ERA, 126 ERA+, 8.5 K/9, 2.2 BB/9 The differences are marginal, a fact that serves as a reminder that Lester (pitcher 1) can use Greinke (pitcher 2 - 6 years, $147 million as a free agent after 2012) and Hamels (6 years, $144 million as an extension months before reaching free agency in 2012) as baselines for establishing his market value. Of course, both Hamels and Greinke were entering their age 29 seasons when they signed their deals, which expire after their age 34 seasons. But, Lester isn't so much older than those two that the market will penalize him significantly. Indeed, given the fact that he's coming off the best year (year-plus, actually, dating to July 2013) of his career, he could be in line for just as many years with an even higher AAV. Model 3: Dustin Pedroia (more years, fewer dollars) Dustin Pedroia wanted to be a Red Sox for life. He was willing to make concessions to do so. Pedroia's priority was both to ensure his future with the only organization for which he ever played and to structure his deal in a way that it would maximize the likelihood of building a winner. He and the team accomplished that with an eight-year, $110 million deal -- a deal that offered him, in absolute terms, a mammoth guarantee of career earnings with security for generations of little Pedroias while maintaining a comparably modest AAV of just north of $13 million a year that would both allow the Sox to pursue other big-money players and protect the team from being hamstrung by his decline years. Model 4: CC Sabathia (opt-out) What if the Red Sox could sign Lester for three years and, say, $72 million? A player opt-out creates just such a possibility. After the 2008 season, the Yankees signed CC Sabathia to a seven-year, $161 million deal that included an opt-out after three seasons and $69 million. At the time of the contract, the industry offered some skepticism about the idea of giving a player added flexibility. In hindsight, it could have been a tremendous coup for the Yankees had they let the left-hander walk after three elite seasons as the anchor of a team that won a World Series. The Sox could consider including an opt-out in a deal for Lester as a means of letting him hop back on the market when he was 33 -- after the team had captured some of the most attractive years of his career. The problem with such a design, however, is that if Lester were performing at such a level that he exercised his opt-out, then the team could find itself in an even more compromised negotiating position with him than it is now. Pressure to re-sign him could be immense, just as it was when the Yankees extended Sabathia for another year in order to prevent him from opting out. On the other hand, it's possible that the team's position would be considerably better than it is now after three more years for some of the young pitchers in the organization to mature. Whereas the Sox have three rotation holes right now including a pair at the front of the rotation, the situation might be somewhat less dire by the time an opt-out came into play. It's worth noting that the Sox recently included an opt-out in Rusney Castillo's contract prior to its final season. Model 5: John Lackey/Cliff Lee/Cole Hamels/Jonathan Papelbon (the vesting option) When an MRI during the pre-signing physical revealed that John Lackey's elbow seemed likely to blow out early in his Red Sox contract, the Sox worked with Lackey to develop a form of insurance -- chiefly, that if he missed a year due to recovery from Tommy John surgery, a team option would vest that permitted the team to add an extra year of control to his five-year, $82.5 million deal at the major league minimum ($500,000 and change). That option did indeed vest when Lackey missed all of 2012, adding considerably to Lackey's trade value this summer when he was dealt to the Cardinals. Lee's willingness to accept fewer years that he could have secured on the open market, meanwhile, may have been abetted by the fact that the Phillies included a provision that would tack on another guaranteed year (in place of a team option) if he met certain innings thresholds in either the fifth (final) year of the deal or over the final two years of the deal. The vesting option represents a form of risk sharing that can sometimes prove agreeable to both sides for longer-term deals. Model 6: Ian Kinsler/Dustin Pedroia (the frontloaded deal) Typically, players are never more valuable than at the beginning of their contracts, with steadily diminishing returns over the life of a deal. In recognition of that fact, some players -- including Pedroia and Tigers second baseman Ian Kinsler -- take larger salaries up front that taper gradually in expectation of their declining performance as they move beyond their prime years. In so doing, the players remain both easier to fit into a team's salary structure during their post-prime performance and they also remain easier to trade.