4. Jon Lester (2010)
It might not be too much of an exaggeration to say that Jon Lester has been one of the better pitchers in the majors over this past decade. Sure, a lot of this comes from what he’s done with the Chicago Cubs over the past four years, but before that he was a huge part of two World Series wins with the Red Sox.
The 57th overall selection in the 2002 MLB Draft developed into a perennial All-Star through his thirteen years within the Red Sox organisation. Lester worked his way up within the Red Sox farm system before making his major league debut in 2006, and soon became a huge piece for this side.
Looking at the seasons he produced, and there were plenty of great ones, his 2010 season is the defining one, at least in the time he spent with Boston over the past decade. 2008 was Lester’s real breakout year, and he followed that up with more of the same in 2009. In 2010, however, he hit new heights. Finishing 19-9 on the season, Lester led the entire majors with 9.7 K/9, as he dominated hitters with his mean four seam and cutter combo.
Lester had an incredible streak where he pitched at least thirty games a regular season for eleven straight seasons, this only ended this past year, as he remains in Chicago. Lester is now a five-time All-Star, three-time World Champion as well as the 2016 NLCS MVP. He’s got a tremendous resume, and it’s great to say that begun with the Red Sox.