Looking at where Jon Lester stands after Clayton Kershaw's contract

Rob Bradford
January 15, 2014 - 8:17 pm

Another shoe dropped Wednesday. Clayton Kershaw -- the 25-year-old who was trending toward serving as next offseason'€™s biggest pitching prize -- has been locked up by the Dodgers thanks to a landmark seven-year, $215 million contract. It is a deal worth more than Justin Verlander'€™s $180 million deal, or the $175 million contract given to Felix Hernandez. He will make an average of  $30.7 million per season -- the highest AAV in big league history, surpassing the standard set by Alex Rodriguez with his 10-year, $275 million deal with the Yankees after the 2007 season. The landmark deal was no surprise. Kershaw is the game'€™s best pitcher already -- with two Cy Young wins in the last three years, and a runner-up finish sandwiched in between those two seasons -- at an almost unfathomably young age. For the time being, Kershaw'€™s deal is an aberration. Not even David Price, who will become a free agent after the '€™15 season, figures to reach such financial heights considering the Tampa Bay lefty is already 28-years-old. Jon Lester is another who won'€™t be making Kershaw money. But the Red Sox starter did just potentially make more money because of Kershaw. With the Dodgers'€ ace off the market, Lester and Detroit'€™s Max Scherzer head into the 2014 season representing the most desirable potential free agent pitchers (with Cleveland'€™s Justin Masterson, the Reds'€™ Homer Bailey and Kansas City'€™s James Shields just a notch behind). First off, according to an industry source, the Red Sox have not started talks with Lester about a possible extension beyond the 2014 season. All signs continue to suggest negotiations will start once spring training rolls around. Kershaw'€™s financials aren'€™t likely to sway Lester'€™s market, but the sudden absence of the L.A. ace on next year'€™s open market is notable. Assuming the Red Sox lefty comes close to his '€™13 performance, he would now join Scherzer as the two options for teams searching for lock-down No. 1 starters. One of those teams looking for a No. 1 after '€™14: The Red Sox -- that is, unless Lester leaves Scherzer as last man standing. These are negotiations the Red Sox would seemingly be a bit more aggressive toward than, say, Jacoby Ellsbury. The five-year, $80 million offer extended to the free agent outfielder let a team like the Yankees creep in. It'€™s an approach --€“ with demand seemingly far outweighing supply --€“ the Sox might not duplicate with Lester. Lester has shown an openness to working out a deal in which he does not put maximizing his worth ahead of his happiness and security. "You sit down with your agent, sit down with your family and realize, yeah, there'€™s possibly millions of dollars that you left on the table. But at the same time, you'€™re secure. Your family is secure,"€ Lester said earlier this offseason on WEEI'€™s '€˜The Hot Stove Show'€™. "You'€™re with the team and you don'€™t have to worry about anything. And the same thing will go here in the next couple months or the next however many months. If you sign a deal before you become a free agent, you'€™re probably most likely leaving money on the table." Lester might very well give the Red Sox somewhat of a financial break, but that doesn'€™t mean John Henry'€™s team won'€™t have to pay. There is an easy jumping off point for the lefty, with L.A.'€™s Zack Greinke (3 months older than Lester, with a 106-82 career record, 3.65 ERA, 8.0 strikeouts and 2.3 walks per nine innings) owning eerily similar regular season numbers to the Sox'€™ ace (100-56, 3.76, 8.1 strikeouts per nine, 3.2 walks per nine) without the postseason resume. Greinke, thanks to a free agent deal he signed with the Dodgers after the 2012 season, owns a six-year, $147 million deal. So there you go. While giving a starting pitcher a contract averaging upwards of $20 million a year wouldn'€™t seem to fit the Red Sox'€™ new profile, it is an avenue they might be able to afford to venture down. Kershaw money? No. Greinke'€™s payday? Perhaps. The reason for the acceptance of a new Lester deal is due to the financial flexibility the rest of the Red Sox rotation offers. Taking a look at the current group, both Jake Peavy and Ryan Dempster come off the books after '€™14, while Clay Buchholz is under the Sox'€™ control through '€™17, never making more than $13.5 million. Also of note is that John Lackey'€™s number drops to the major league minimum for the final year under Sox'€™ control in 2015. Then you have pitchers like Felix Doubront, Brandon Workman, Allen Webster and Henry Owens who have top-of-the-rotation potential, yet reside years away from their free agent hauls. Let'€™s say Lester takes a deal averaging $25 million per year for six seasons. For the next four campaigns, the Red Sox€™ starting staff could very well make up no more than about $45 million in any of those years. That'€™s manageable, especially considering the kind of quality you would likely be getting. For example, this year'€™s rotation is going to cost the Red Sox slightly more than $65 million for 20€™14. (For what it's€™ worth, the Dodgers'€™ starters will combine for more than $90 million in the upcoming season.) It remains to be seen how Kershaw exiting next year'€™s free agent class translates. The guess here? In the short-term, the payoff for Lester might be more of a sense of urgency from the Red Sox. And if no resolution is found come next November, those still looking for an ace could push Lester into a financial stratosphere closer to Kershaw than the Sox'€™ hurler could have ever imagined.