Cubs News

Top Cubs offseason questions: Will Jon Lester return in 2021?

3 years agoStaff Report

With the Cubs facing a pivotal winter, we’re tackling the biggest questions facing Jed Hoyer’s front office. Reporters Bruce Levine and Tony Andracki provide their perspective.

Next up:

Will Jon Lester return to the Cubs in 2021 and how will the rest of the rotation fill out?


Hoyer talked about the fact that he’s been in contact with the agents for Lester. That conversation is probably going to continue to go for a while. Lester told us at the beginning of the offseason that he might have to wait to see how everything shakes down with the Cubs — what they do as far as adding to the rotation and their pitching staff. I think he’s going to be patient about that.

As far as the rest of their staff, you certainly have Kyle Hendricks and Yu Darvish at the top, but Alec Mills and Adbert Alzolay are still somewhat question marks. They’ll probably be penciled in at 3 and 4 in the rotation. But there’s still a long way to go before spring training starts. The additions might come from trades moving down the line. I’m just not sure how Lester fits into this year right now.

The Cubs have 22 pitchers on their 40-man roster, so from that perspective, they are probably looking for lightning in a bottle from some of the arms that they have brought in over the last two years and I think they’ll continue to look at that regardless of what they’re able to do in the trade or free agent market.


The Cubs are going to need all the pitching depth they can get. If there is the right fit — especially financially for both sides — then I do think there is still a reunion in the cards for Lester coming back to Wrigley Field.

The Cubs are going to need far more than five starting pitchers for next year. As of right now, they basically only have four starters. There is the potential for Lester to come back, but the unknown aspect is if another team swoops in and gives him more money or a different opportunity that he might not necessarily have here.

Ultimately, I think the best opportunity for him personally is in Chicago, pitching for David Ross and pitching in front of fans at Wrigley Field in a city that he loves.

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