Lester has averaged a 4.3 WAR per season going back to 2008 and in that time has only finished with a WAR less than 3 once, in his disappointing 2012 season. His great numbers as well as his postseason experience make him a valuable ace for any pitching staff.
Here are the teams lining up for Lester.
With the highest reported offer of $138 million the Cubs have proven that they are willing to go far for Lester. As the Cubs attempt to rise from the bottom of the NL central to break their world series drought that dates back to 1908 they are looking for an experienced ace to lead their team of young players. Only three Cubs players are over 30, Edwin Jackson, Justin Ruggiano and Tsuyoshi Wada (who is 32 but only made his debut this past July). If the Cubs can sign Lester he will be a strong leader and a great role model for his teammates.
Boston Red Sox
The Red Sox are looking for starting pitching because their rotation's only sure starters are Joe Kelly and Clay Buchholz both of whom have been injured often throughout their careers. Lester is clearly their first choice because he already knows the team, and they already know how good he is. After contracts to both Pablo Sandoval and Hanley Ramirez accumulating to a value near $200 million Lester could be out of their price range. The Red Sox are however a very rich team so they were still able to offer a rumored $130 million contract, but can they go further and beat the Cubs $138 million offer, this seems unlikely however Sox owner John Henry is still "hopeful" that the Sox will be able to acquire Lester. If the Sox are able to sign Lester it would prove their trade deadline move this year a genius move in which they essentially traded Johny Gomes and about 2 months of Jon Lester's services for Yoenis Cespedes.
San Francisco Giants
The Giants are rumored to be interested in any of the three big free agent starters (Shields, Lester, Scherzer). They are hoping to create another world series team after winning in 2014, '12, and '10. After losing out on bringing back Sandoval and signing Yasmany Tomas they look to pitchers as their next available position to upgrade after Jake Peavy and Ryan Vogelsong became free agents.
Los Angeles Dodgers
The most recent team to enter the mix is the Dodgers. They have proven that they are willing to go far for quality free agent pitchers in the past by signing Zack Greinke to a 6 year $147 million contract before the 2013 season. A deal for Lester would be around the same size, and would make a ridiculous rotation of Kershaw, Greinke, Lester, Ryu, Haren. Lester could soon become the newest edition to the largest payroll in baseball for the Dodgers.