The 30-year-old Lester has never hit the open market over his career, as the Red Sox bought out some of his free agent years with a six-year, $42.75 million extension that covered from 2009 to 2014. He has pitched with them since the beginning of his career and now will take the next step.
Lester, a Tacoma, Washington, native was drafted by the Red Sox in the 2nd round of the 2002 MLB Draft. He worked quickly through the minor leagues, even netting him as the 22nd best prospect prior to the 2006 season as ranked by Baseball America. Lester came up to the bigs that year and has never looked back, appearing in the major leagues every year since.
The three-time All-Star Lester has a ton of big game experience. Lester was a part of two World Series runs, in 2007 and 2013, and played an instrumental part in the Red Sox last title, posting a 1.56 ERA in 34 2/3 innings pitched during the postseason (not quite Bumgarner numbers, but Bumgarner isn't human). Over his career, Lester has logged 1596 innings and posted a 3.58 ERA.
Lester spent his first time outside Boston this past season, being traded to the Athletics midseason for Yoenis Cespedes and others. He made 32 starts with the two clubs, going 16-11 with a 2.46 ERA and a 2.80 FIP. He was a 6.1 fWAR player, the second-highest mark of his career.
Lester still has a lot left in the tank. He's been one of baseball's best starters since breaking on to the scene in 2008. He logged over 200 innings his first three seasons beginning in 2008, then worked 191 2/3 in 2011, and has worked over 200 every year since. But he is still only 30. Lester is the true workhorse in this free agent class, which will net him a big contract over many seasons.
I'm not sure the Athletics can afford to bring Lester back, but I know the Red Sox would love a reunion. After being dealt, Lester felt "no hard feelings" towards Boston, and would be interested in coming back in the offseason. I'm not buying it now though. The Red Sox have $90.3 million committed to eight players already in 2015 and have $22.5 million committed to two in 2016. I'm not sure they can take on another $20 million per year by bringing back Lester.
I do think the Cubs are going to busy this offseason. Chicago is this close to contention next year and has a lot of payroll flexibility to get them there. They have $24 million guaranteed to four players next season. That's it. With that in my mind, and the fact that they are reportedly going all out for pitching this offseason, I have them signing Lester to a five-year, $120 million contract.