Throughout the history of the Chicago Cubs, they have accumulated quite an impressive collection of Hall of Famers with their names now in Cooperstown. That said, the last player to be inducted was Fred McGriff in 2023, who was voted in by the Veterans committee, now called the Era’s committee. Greg Maddux, in 2014, was the last player enter through selection by the Baseball Writers Association of America (BBWAA).
With the 2026 selections having been finalized, a look towards 2027 shows that former Cub Jon Lester will be eligible for the ballot for the first time. Other former Chicago players who could appear on the ballot include Jake Arrieta and Dexter Fowler, but it’s Lester who has the strongest case to enter the Hall of Fame immediately.
Ex-Chicago Cubs’ World Series winner Jon Lester has strong 2027 Hall of Fame chances
Nov 4, 2016; Chicago, IL, USA; Chicago Cubs starting pitcher Jon Lester (34) lifts the Commissioner’s Trophy during the World Series victory rally in Grant Park. Mandatory Credit: Dennis Wierzbicki-USA TODAY Sports
Jon Lester enjoyed a remarkable 16-year career, making 452 starts with a 3.66 ERA. He was a five-time All-Star, won three World Series titles, and earned League Championship Series MVP honors in 2016, helping lead the Cubs to their first championship in 108 years. Lester was consistently clutch in the postseason, a factor that should weigh heavily in Hall of Fame considerations.
Six of Lester’s 16 seasons were spent in Chicago, where he posted a 3.62 ERA, earned two All-Star selections, and finished second in Cy Young voting in 2016. That year was particularly impressive: he logged 202 innings with a 2.44 ERA, arguably the best season of his career.
Taken together, Lester’s longevity, consistency, and ability to excel in high-pressure moments make a compelling case for Hall of Fame induction. His combination of regular-season success and postseason heroics positions him among the premier pitchers of his era, and many argue he deserves serious consideration in the next voting cycle
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