Jon Lester is one of the most important players in the history of the Chicago Cubs. He is one of the first people to realize that they were building something special so he signed with them when he became a free agent. He then was one of two aces on a staff that led them to a World Series championship in 2016. There was a lot of success during his time with the Cubs.
Unfortunately, things didn’t end the way you’d like to see them end between an organization and a superstar like Lester. He wanted to take a discount to come back to the Cubs but they didn’t want him. The Cubs believed they were a winning team going into 2021 but they didn’t think Lester could help with that. They were wrong.