The Cubs offseason has more questions than answers

I’ve been trying to think about what to write about the denouement of the Cubs 2020 season for almost two weeks now. It’s not really writer’s block so much as it just doesn’t seem like there is any angle that is particularly interesting to explore. Actually, scratch that - there are a lot of angles that are interesting to explore and they are all super depressing. Since I’ve been clinging to baseball in 2020 as a break from the general suckiness of, well, everything, I guess you could say I’ve been avoiding delving too deeply into baseball analysis and prognostication for my own mental health.

So, I decided to rip the band-aid off today. Here they are, in no particular order, the three topics I find myself thinking about dwelling on relative to the future of the Cubs these days.

The Offense

The offense has been broken since at least 2018 when Theo Epstein acknowledged as much in his end of the season press conference. For reasons I still don’t entirely understand they parted ways with John Mallee after 2017 and it’s been downhill ever since. The 2018 Chili Davis experiment was a disaster. The 2019-20 Anthony Iapoce years have somehow managed to be even worse. This is far more than a coaching problem, though. It’s also reflective of some player decisions that have gone about as poorly as one could imagine.

For example, the loss of Ben Zobrist due to personal reasons for most of 2019 was a huge blow to a team that was just beginning to fire on all cylinders. Even in a down year his OBP was .358 — the man gets on base and makes contact, something the rest of the team has struggled with at times.

Then there was the mind boggling decision to let Tommy La Stella go for nothing while replacing him with the “veteran presence” of Daniel Descalso. Far from being exploited with more playing time with the Angels and Athletics La Stella has thrived. Imagine his contact bat and the 8.7 percent K rate he put up in 2019 getting the bulk of starts when Zobrist needed time off instead of splitting time between Descalso, Addison Russell and David Bote. Actually, don’t do that to yourself. It’s just depressing.

This offense seems to only have two settings - crooked numbers or nothing. While it looks like Nico Hoerner may develop some of those on base and contact hitting skills, his wRC+ of 63 across 126 plate appearances in 2020 indicates he’s a player would could still use some time developing those skills in Triple-A. You know, if Triple-A is still a thing after MLB gets done demolishing the minor leagues.

Which leads me to my biggest concern about this offensive rut the Cubs have been in for multiple seasons now: this offseason is probably the worst possible time to retool an roster. The biggest contracts in the Cubs core will expire after 2021 and the vast majority of those players had their worst offensive seasons during the pandemic shortened season. It’s not entirely clear what baseball will look like in 2021, but given the financial woes (or purported financial woes) around the league it’s not a really good time to turn current players into future assets.

2020 was basically the last hurrah for a beloved core of Cubs players who tried their best but just haven’t been able to break out of their offensive rut and this offseason is basically the worst possible time to fix that problem.

Jon Lester

Jon Lester is the greatest Cubs free agent signing of my lifetime and maybe of anyone’s lifetime. He has done absolutely everything Cubs fans hoped and dreamed. The borderline Hall of Fame pitcher came in to anchor the rotation on a young team and help them end the longest championship drought in sports. He deserves a year-long send off that rivals the one David Ross received and at least as many standing ovations.

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Instead he’s staring down a team option he knows will not be picked up as his decline accelerated this year. While I’d still take Lester’s grit and guile in the postseason over 95 percent of pitchers in MLB, I’d also have the quickest hook the second something looked like it was going wrong. The Cubs need to figure out a way to bring Lester back to Chicago in 2021 so we can give him the sendoff he deserves. It seems unlikely that sendoff will involve hoisting another Commissioner’s Trophy and a sellout next season might be 12,000 fans, but it’s the only correct answer. I very much hope the front office clears this up sooner rather than later.

The Theo Epstein Era

I will never forget the day the Cubs announced that Theo Epstein would be leading their baseball operations. I was standing in the teachers’ lounge in a suburb in Boston. My colleagues were all heartbroken and horrified as I literally did a jig at my desk. I was sure that Theo was going to bring a World Series Championship to Chicago and he did just that.

Photo by Jonathan Daniel/Getty Images

But that era is coming to a close. 2021 will be the last year of Theo’s contract and it seems unlikely that there will be another extension since he’s been remarkably transparent that he believes a decade of leadership is enough for an individual in any organization. I have zero doubt that Theo will do whatever he can to position the Cubs to succeed in 2021 and beyond, but it also means that for the first time in nine years there is a bit of uncertainty regarding the future of the Cubs baseball operations team.

That uncertainty will coincide with a year where trades and free agent acquisitions will be tricky for reasons I’ve already discussed. It’s also likely to be tricky because after the 2021 season MLB and the MLBPA will enter what most believe will be the most contentious Collective Bargaining Agreement negotiation in decades. That basically means whoever takes over for Theo (it’ll almost certainly be General Manager Jed Hoyer) will be taking the reins after two years of radically reduced revenue from the pandemic, with most of the core contracts expired or expiring, and a historic labor fight.

Buckle up, Cubs fans. It’s going to be a bumpy ride.