Jon Lester was a major signing for the Chicago Cubs when they were just finished rebuilding. Signing him was proof that they were now trying to win it all and they did. He was brilliant for them during his run but his time there is likely up. They have a team option with him where they could either pay him 25 million to stay or ten million to leave. With his stats in 2020, it seems like they would be smart to let him go and avoid paying that kind of money.
He isn’t the elite Hall of Fame pitcher that he once was but he might have a lot of value to the White Sox if he came over. For one, he would bring three World Series rings worth of experience to a very young team that needs as much leadership as it can get. He won it all twice with the Boston Red Sox and once with the Chicago Cubs so doing it with more than one organization is already a proven skill.
If he came to the White Sox, there is a good chance that he would be either their fourth or fifth pitcher in the rotation. He wouldn’t be the guy coming in to be the new ace-like he was with the Cubs but he would be more of a depth piece that can make spot starts and help them in the bullpen if needed. From an experience and performance standpoint, this could prove to be a really smart signing for the White Sox (or any potential young team).