Cubs Not Ready to Close Door on Jon Lester Reunion, Other Roster Issues Have Top Priority

Jed Hoyer covered quite a bit over the course of his conference call following the conclusion of the Winter Meetings even though nothing much happened during the virtual event. Since the Cubs made only minor ripples with the addition of three right-handed pitchers via the Rule 5 Draft, there’s still a lot of work to be done in order to get the roster ready for spring training and what they still believe can still be a competitive roster in 2021.

As strange as that may sound, consider that the rest of the NL Central appears to be just as frugal as the Cubs, if no more so, and none of the other four teams figures to make moves aimed at improving markedly for the coming season. Hoyer downplayed the idea that trading Kris Bryant is a foregone conclusion and has said Kyle Schwarber could even return, plus they’ve still got plenty of room under the luxury tax if they choose to do anything.

With the team in need of rotation depth, Jon Lester could be brought back for a return engagement if things work out.

“We’ve been very consistent in our communication with his representatives,” Hoyer told members of the media. “If things could work out, we’d love to have him back. I think we have to figure some things out first. Obviously, that kind of goes without saying, because otherwise something would be done by now. There’s some things we want to work through first.

“What he’s done for us is amazing, and certainly we’re not ready to close that door.”

When Hoyer says they have to figure some things out, he’s talking about both Lester’s value and how high a priority it is to bring him back. Jason Heyward and Ian Happ the only two outfielders remaining on the big league roster, so Hoyer made the obvious admission that beefing up that portion of the roster is “something that we’ve certainly prioritized.”

That could mean giving Nico Hoerner a little more time in center, even if it’s just on a part-time basis, something the Cubs development staff teased last January and that we saw briefly during the shortened season. But that would really just be more of a stopgap, so the Cubs need to find at least two more outfielders. Though Hoyer said they’re comfortable with Happ in center, you have to believe they’d prefer someone who can push him to left.

Should they be able to do that at a relatively low cost, ideally with someone who displays a contact-heavy hitting approach, there might be a little room left in the budget to go with a younger, more dynamic starting pitcher. Perhaps someone looking for a pillow contract or who’s willing to take a very reasonable two-year deal. Lester might be more of a fallback, assuming he’s amenable to a deal like the one Adam Wainwright got from St. Louis a couple years ago.

For as much as he’s meant to the Cubs organization as a stud starter and usher of the team’s long-awaited title, Lester can’t be a priority for the Cubs right now. Nor should the Cubs be a priority for Lester, who is probably looking for at least one last shot at another championship. If he’s only fielding one-year deals, Chicago — at least the North Side — isn’t the most attractive spot from an odds perspective.

There’s more to it than that, of course, like having the chance to bid a more formal adieu to the fans at Wrigley. Then again, Lester could do that in a different uniform even if that would make the event significantly more bittersweet.

If emotion rules the day, there’s a chance we see the aging lefty back with the Cubs in ’21. If both sides are dealing from a more pragmatic perspective, however, I don’t see any way he returns.

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