He started off that season with Boston and was later traded to the Oakland Athletics.
He was viewed as one of the best left-handers available in the market, yet the Red Sox opted to let him go.
According to Red Sox insider Pete Abraham, they should have re-signed Lester.
“In 2014, Red Sox did not want to invest in Jon Lester, who was built like a linebacker. He played seven more years and didn’t miss a start. He could probably give you 5 innings today if you needed it. In 2019, they went all in on a pitcher nicknamed Stickman.”
In 2014, Red Sox did not want to invest in Jon Lester, who was built like a linebacker. He played seven more years and didn't miss a start. He could probably give you 5 innings today if you needed it.
In 2019, they went all in on a pitcher nicknamed Stickman.
— Pete Abraham (@PeteAbe) August 9, 2022
Abraham added: “To be certain, they did try and sign him after trading him. But they could have easily had him locked up in spring training (and for a lot less) and blew it.”
The Red Sox Missed Lester
The Red Sox did win the 2018 World Series, but who knows if Lester could have helped win more.
After all, he helped the Chicago Cubs break their own curse in 2016 as a member of that unit.
In the winter of 2014, Lester put pen to paper on a six-year, $155 million deal to play in Chicago.
Missing an ace, they traded for Chris Sale before the 2017 season, and the southpaw was great that year.
His health started to deteriorate in 2018, and he hasn’t been the same ever since after the stress he put on his arm during his Chicago White Sox days and some fluky injuries.
In hindsight, perhaps the Red Sox would have been better off re-signing Lester.
It’s hard to say if that move would have resulted in more rings, though.