BOSTON (CBS) — The Red Sox drafted and developed Jon Lester. In their organization, he became one of the best and most reliable left-handed starting pitchers in all of baseball and helped them win two World Series. He remains one of the best and most reliable lefties in the bigs, though he’s doing it for the Chicago Cubs.
That’s not generally how things are supposed to work, and Red Sox principal owner John Henry admitted as much on Monday in Fort Myers.
Henry pulled no punches, telling reporters that the Red Sox simply blew it when it came to signing Lester to an extension in the spring training final to the final year on his deal.
The Red Sox reportedly offered Lester a four-year, $70 million contract prior to the 2014 season. He ended up signing a six-year, $155 million contract with the Cubs the following offseason.
During that 2014 season, Lester went 10-7 with a 2.52 ERA before the last-place Red Sox traded him (and Jonny Gomes) to Oakland in exchange for Yoenis Cespedes. The Red Sox would then flip Cespedes to the Tigers in the trade for Rick Porcello that following winter.
Since signing with the Cubs, Lester has made 32 starts in each of his four seasons, compiling a 61-31 record, 3.33 ERA and 1.186 WHIP. He also earned NLCS MVP honors in 2016, en route to leading the Cubs to their first World Series championship in 108 years. In 12 playoff appearances (10 starts) for the Cubs, Lester has a 2.44 ERA and a 0.957 WHIP.
After a last-place finish in 2015, the Red Sox went out and dedicated big money to David Price, a left-handed pitcher on the wrong side of 30. It was, essentially, the exact move which the team vowed to never make when it decided to send Lester packing. That signing alone was as much of an admission of fault as anything.
That is, until Monday, when Henry made it as clear as possible.