In the year 2000, the two most cursed franchises in baseball were the Chicago Cubs and Boston Red Sox. Given their history of bad luck, many believed it would be another hundred years before either of these big market teams won a championship. While Jon Lester did not break these curses (he wasn't in the Majors when Boston broke it in 2004), he played a significant role in two squads that had been struggling for decades.
Lester was a second-round pick by the BoSox in 2002 and joined the main roster in 2006. While he played well, he had enlarged lymph nodes that required off-season treatment. Fortunately, Lester recovered and returned to the Red Sox the following summer, where he gained a win in the 2007 World Series, his first championship. After that, Lester became a high-end starter.
In 2008 and 2009, Lester won a combined 31 games with 377 strikeouts. He went to his first All-Star game in 2010, led the AL in SO/9 (9.7), and was fourth in Cy Young voting. He struck out 225 batters, with a 3.25 ERA and a career-high 19 wins. He was an All-Star again in 2011 (15-9, 3.47 ERA) but slipped in 2012 (9-14, 4.82 ERA), which was cause for concern in Fenway.
However, in 2013, Lester rebounded and went 15-8. His postseason was phenomenal as he went 4-1, including two wins in the World Series with a 0.59 ERA. He went to the All-Star game again in 2014, but the struggling Red Sox traded him to the surging Athletics for their playoff run. Although Oakland did not get past the first round, Lester's overall season was his best in years, as he finished fourth in Cy Young voting with an overall performance of 16-11, 220 strikeouts, and a 2.46 ERA.
Lester became a free agent and signed with the Chicago Cubs. He had his ups and downs with the Cubs, but his up years were memorable. He won 19 games in 2016 with a 2.44 ERA and was again an All-Star. Most importantly, Lester led Chicago to their first World Series win in over a century, and he won the NLCS MVP and was named the Babe Ruth Award winner. He was an All-Star again in 2018 (his fifth), but he struggled afterward and retired after brief runs in Washington and St. Louis.
Lester retired with three World Series rings, an even 200 wins, and 2,488 strikeouts.
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