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If he is in, then Cole Hamels is certainly in. by No Right Turn on Red
Both pitchers had remarkably similar careers. Both debuting in 2006 at age 22 with only 42 innings pitched over 29 games separating the two (Hamels retired last year).
Hamels has Lester beat in every important category: ERA (3.43 to 3.66), ERA+ (123 to 117), FIP (3.68 to 3.78), WHIP (1.183 to 1.278), K (2560 to 2488), BB (767 to 892), Hits/9 (8.1 to 8.6), Walks/9 (2.6 to 2.9), Ks/9 (8.5 to 8.2), K:BB ratio (3.34 to 2.79), bWAR (58.3 to 44.3) and fWAR (51.6 to 46.2). Those WAR gaps are pretty large.
The only thing Lester has over Hamels is wins (200 to 163) and one extra All Star appearance. Lester's Red Sox and Cubs teams had a .555 win percentage while he was with those teams. Hamels' Phillies, Rangers, and Cubs teams went .522 while he was on those teams. Hamels has both an NLCS MVP and a WS MVP. Both had four seasons getting top-10 Cy Young votes.
I'm not necessarily arguing against either candidate, but there's a logjam in the ballot right now (because the process is broken), and I have a hard time putting either in the Hall when a guy like Johan Santana, who was a more dominant pitcher than both, couldn't even get 5% his only year on the ballot.
P.S. Lester debuted in 2006, two years after the Red Sox ended their drought.
EDIT: Lester's WAR will hurt his case. Of all the players who finished their careers with between 40 and 50 WAR, only 21% have made the Hall of Fame, almost all of them guys who retired before ND's last national championship. Jack Morris is the most recent pitcher with that low a WAR to get in the Hall, and it took the Veterans' ballot to get in. I don't see an easy path for Lester beside having played in two major markets.