We know the Cubs could bring Jon Lester back in 2021. My question is: Do you think the Cubs should re-sign him? Give me a reason why they should bring him back for a seventh season.
-- Jack P., Chicago

My initial answer here is "Yes, the Cubs should try to re-sign Jon Lester." Some of the reasoning is just the fact that the team will have money invested in the veteran lefty whether or not he's back in '21. The Cubs will have to pay him a $10 million buyout rather than pick up his $25 million option.

With that much money already assigned to Lester one way or another, then exploring a way to keep him on a team-friendly salary makes sense. As with anything, it all comes down to the cost. If Lester is open to a cheap one-year deal with incentives built in, and the pact does not negatively impact other offseason goals, then I say it's a worthwhile reunion.

Beyond that, there is the issue of rotation depth.

Chicago heads into this offseason with Yu Darvish and Kyle Hendricks locked in atop the starting staff. Alec Mills has earned a spot as well, and Adbert Alzolay is poised to grab another job next year. Behind that group is a bunch of uncertainty, especially with Tyler Chatwood and José Quintana set for free agency.

The Cubs will need to address rotation depth in some capacity. Maybe that's trying to reel in a cost-effective, controllable starter via trade. That will surely be a priority in any trade talks involving Chicago's core players. The Cubs also could use some more depth arms in addition to their internal options.

Lester also had a relatively decent year as a No. 4 starter in the abbreviated 2020 season. If you look at the pitchers with the fourth-most starting innings for each team this season, Lester ranked first with 61 innings. The 29 pitchers in that category averaged 0.4 WAR (Fangraphs). Lester had 0.3 WAR.

That group of 29 averaged around 39-40 innings. Lester's 5.16 ERA was bloated by two awful starts against the White Sox (accounting for 15 of his 35 earned runs). Still, his overall ERA was better than nine of the 29 other pitchers in that grouping.

You could do much worse for a No. 4 starter, and Lester brings with him a wealth of experience. If the Cubs will be shifting younger as part of a transitional season, his leadership would be valuable. So, if you ask me, there are plenty of reasons to bring the lefty back on a one-year deal.

Which of the Cubs' free agents do you think should be the top priority for re-signing?
-- John B., Rockford, Ill.

This seems like a no-brainer to me. The Cubs should try to re-sign righty Jeremy Jeffress.

When Chicago's bullpen was going through issues early in the season, Jeffress was the stabilizing presence that bought time for Craig Kimbrel to get back on track, and for manager David Ross to get a rhythm for how to best use the group. Jeffress was leveraged in a variety of situations and rarely flinched.

Jeffress ended with a 1.54 ERA in 23 1/3 innings, including 9 1/3 innings that were considered high-leverage work. In that sample, he limited batters to a .143/.265/.286 slash line with a .236 wOBA. Jeffress ranked fifth among MLB relievers with 1.52 Win Probability Added in '20.

Jeffress has positioned himself well to see what his season can do for him on the open market. That said, it would make sense for the Cubs to be open-minded about trying to trade Kimbrel, as the team explores some cost-cutting measures with the longer-term picture in mind. In that scenario, keeping Jeffress makes a heap of sense.

Who are some under-the-radar names that you think the Cubs could target this offseason either by trade or free agency?
-- Trenten H.

It's far too early to have a great gauge on possible trade targets, so stay tuned on that front. It's also difficult to know what needs might surface in the wake of potential trades. If Chicago subtracts from its core group, it will then be easier to identify possible targets.

With those caveats out of the way, the current roster presents similar needs as a year ago. A right-handed complementary bat for corner outfield would make sense, as would a lefty complement for second base. I think trying to re-sign Cameron Maybin as an extra outfielder would be a logical move.

If outfielder Domingo Santana becomes a free agent, it could be a buy-low option with some upside as an extra outfielder. He is coming off a brutal 2020 with Cleveland but has had bursts of production in the past, especially against lefties (.820 OPS in '19, and .892 OPS in '17).

At second base, it's possible the Cubs take a similar approach as they did by signing Jason Kipnis as the lefty counterpart to either Nico Hoerner or David Bote. Kipnis had a .799 OPS against righty pitching in 2020. Maybe Cesar Hernandez isn't completely "under the radar," but he's intriguing as a switch-hitter with good contact ability and solid production against righties.

If the Yankees are looking for a catcher, could the Cubs trade Willson Contreras for a guy like Gleyber Torres and a starter?
-- Dave O.

I won't get into that Yankees-specific scenario, but you do bring up one great point that will be intriguing to follow this offseason. There is so much focus on the group of Javier Báez, Kris Bryant and Kyle Schwarber as trade chips, because they could become free agents after 2021. However, Willson Contreras is under control through '22, and that extra year could be a big deal in trade conversations. I think locking Contreras up with an extension is what the Cubs should try to accomplish, but there is no escaping the reality that he might be the best trade chip of the lot this winter.

Ross seemed to use Hoerner as a super-utility man in '20. Do you think next season Hoerner will be given the opportunity to stick at one position on a full-time basis?
-- Zack L., Chicago

Nico Hoerner did not have a great offensive showing in 2020 (63 wRC+), but his defense (five Defensive Runs Saved between second, short and third) was solid. Ross did his best to find the right games to have Hoerner and his contact-based approach in the lineup. I do think Hoerner will grow into an everyday job, but the young infielder still has to improve his offensive profile before being handed the keys. That's why I still think Chicago will be looking for complementary infielders for '21.