Jon Lester
Accomplished: Chicago Cubs, 2018
Lester is the only other pitcher in this club. Lester has seen a lot of the American League postseason and a majority of it was with the Red Sox.
Lester began his career in 2006 and had plenty of national attention because not only was he a valued prospect, but a cancer survivor.
Baseball has many individual battles and titles and championships to attain, but Lester’s greatest victory has to be beating cancer.
It didn’t take long for Lester to find himself pitching in the postseason either. The five-time all-star first helped the 2007 Red Sox collect their second trophy in three years when they swept the Rockies.
He didn’t actually start in the division series until the next year but there would be no title defense after they got bounced by the Rays in the ALCS.
He never got to pitch in the AL wild-card game until 2014 as a member of the Oakland A’s. That was unfortunately as far as that A’s team got.
All of his National League postseason appearances were as a member of the Cubs, and he collected his third ring and the Cubs’ first in 106 years in 2016. In 2015, he and Rodney collected their NL firsts in the postseason.
ALWC: Oakland Athletics, 2014
NLWC: Chicago Cubs, 2018
ALDS: Boston Red Sox, 2008
NLDS: Chicago Cubs, 2015
ALCS: Boston Red Sox, 2007
NLCS: Chicago Cubs, 2015
WS (AL): Boston Red Sox, 2007
WS (NL): Chicago Cubs, 2016
Also in this group, a former teammate of Rodney, and a recent teammate of Lester.