Cubs Will Be Active in the 2020 Offseason

Image for Cubs Will Be Active in the 2020 Offseason

Whether via trades, free agent signings, waiver claims, or whatever, the bottom line is that the Cubs will be active in the 2020 offseason.

My good friend Conner Dempster wrote an article earlier this morning, outlining what the Cubs’ choices may be as the offseason moves forward. In the article, Conner examined the possibilities of the Cubs retooling or heading straight into a rebuild, the latter being something no fan or team wants to endure. Unfortunately, I think the answer lies somewhere in between. Are the Cubs going to go bare-bones and into a rebuild? No. Will they do even worse and intentionally tank? No, but I think there’s going to be quite the shakeup.

Nobody questions the Ricketts’ family’s reluctance to spend money lately, at least on quality players. Somehow, Theo Epstein came out of last winter looking good, signing players like Jason Kipnis, Jeremy Jeffress, and others who performed, but then there are the albatross contract decisions they’ve made, regarding players like Jason Heyward. To Heyward’s defense, he’s coming off his best season in Chicago, but then again, it only took five years of his $184M deal to do so.

By the way, despite how things may appear, the Cubs had the third-highest 28-man roster payroll in 2020 ($66.1M), coming in behind the Yankees ($77.2M) and the Dodgers ($77.1M). In terms of overall payroll, the Cubs placed seventh this year, writing checks worth $75.6M.

For the Cubs to become active in the 2020 offseason, they do have a variety of methods to choose from.

Being Active in 2020 Means the Cubs Start Cleaning House

MLB only allows you to hold so many players on the roster (26 and 40-man), so if the Cubs are to be active this offseason, they’ll certainly need to be saying goodbye to some players. Unfortunately, some of those will likely include names and faces who’d become staples on the Cubs’ roster.

Everyone ages, and when those who are aging begin to underperform, the team has a trio of saving grace options: Trades, not re-signing free agents, and team options. In the 2020 offseason, the Cubs have a plethora of choices to make in these departments.

The Ultimate in Offseason Activity: Exercising Team Options

The Cubs have a few players who are would-be free agents this season, assuming the team doesn’t pick up the options they have on them.

Headlining the team option activity this offseason will be LHP (starter) Jon Lester. Big Jon has been a pillar in the Cubs’ rotation for the last six seasons, but now the Cubs have a choice to make. Chicago holds a $25M team option on Lester for next year, but Lester’s numbers have slipped over the past couple of seasons.

At age 37 (in January), Lester has a $25M salary due to him in 2021, that is, unless the Cubs choose to buy him out for $10M. Either way, Lester costs the Cubs $10M for 2021, the question is, will he be worth an additional $15M before he becomes an unrestricted free agent in 2022.

Lester has eluded that he’s pitched his last game at Wrigley in the final week of the season, so it doesn’t sound like he’s expecting the option to be picked up. If the Cubs are to be active in the winter of 2020-2021, Lester may find himself cleaning out his locker… for good. Fifteen million could go a long way in terms of filling other voids the Cubs need to address,

“[I’m] very sad right now because my focus today was to have Lester pitch one more start at Wrigley. That was my goal today and I couldn’t make that happen. I’m very disappointed.” -Yu Darvish after losing to Miami in the NLWC Series.

Next on the list for team options is the Cubs’ unofficial captain, first baseman Anthony Rizzo. Here’s where things get a little interesting, and to be quite frank, here’s where Tom Ricketts has a chance to look like a real ass.

Rizzo, who signed the ultimate team-friendly deal in 2013, agreed to play for Chicago on an eight-year (2013-2020), $60.5M deal (AAV $7.562M per year). Rizzo has been a leader, and he’s been a large part of the heart and soul of the Cubs for eight years now. The problem is, his offense has been slipping.

In 2020, Rizz put up a slash line of just .222/.342/.414, which pales in comparison to his 2019 slash line of .293/.405/.520 (OPS of .924). While 2019 saw Anthony smash 27 homers and plating 94 RBIs, 2020 was much different – just 11 homers and 24 RBIs. Yes, 2020 was much different with just 60 games (37% of a 162-game season). Proportionately Rizz actually hit about the same amount of homers that he did in 2019, but RBIs matter too, and he would have needed to plate a good amount more to have contributed as he did in ’19.

A lot of big-name players – and not just those on the Cubs – had a down year at the plate this season. If the choose to Cubs exercise their team option on Rizzo, it’ll cost them $16.5M for 2021; if not, he’ll be traded. Is Rizz worth the $16.5M? Absolutely. Including that money, Rizzo’s deal would max out at a total of nine years and $77M – which works out to an AAV of just $8.56M a year – a steal for a player of his caliber.

If the Cubs choose to keep their 3x Gold Glove first baseman, it’ll likely only be for 2021. The teams stated objective over the course of the last offseason was to extend SS/2B/3B Javier Baez, but those talks stalled and no extension was ever reached.

Rizzo is going to want (and rightfully deserves) a rather large contract extension, but at age 31-1/2, will Tom Ricketts approve a deal after the 2021 season, or will he settle for all of Rizzo’s contributions, the cheap paychecks over the last eight (or nine) years and let him walk away as a free agent?

To Re-Sign or Not to Re-sign: Impending Free-Agents

In the impending free agent realm, the Cubs are going to have quite a lot of choices to make. They not only picked up some rentals at the trade deadline, but they also have more than a few guys who’s contracts expired with the final loss to Miami last week.


In addition to the option on Jon Lester, the Cubs have two additional starters who’ll be (or could be) free agents in less than a month.

Jose Quintana cost the Cubs a ton (Eloy Jimenez, Dylan Cease and a total of $26,707,590 in cash), but he was what the Cubs needed when they needed him. I’ve always described Q as a workhorse, operating mostly under the radar, yet quietly solid.

Quintana will be turning 32 on January 24th, and his career numbers (3.73 ERA and a WHIP of 1.266 – while not bad – may not warrant the extension that he and his agent may ask for. Without Lester, the Cubs will be down to zero southpaw starters, and Q may be the better (and certainly cheaper) of the the pair, if the Cubs choose to keep one or the other. Don’t count on it though.

Then there’s Tyler Chatwood. Chatwood signed a three-year (2018-2020), $38M deal with Chicago, and in 2018 couldn’t hit the strikezone had his life depended on it. Pitching coach Tommy Hottovy turned Chatty around by 180 degrees, but Joe Maddon bastardized Chatwood, leaving him to languish in the bullpen in 2019, often going more than a week between appearances.

Chatwood jumped off to a great start in 2019 but incurred an injury that affected not only his pitching but his season and a possible extension. At age 31 (December 16th), Chatwood could be a viable option for an extension. If not, the Cubs – including Quintana and Lester – face losing 60% of their starting rotation, while being without a swingman in the pen.

Also due for free agency are 2020 rentals Jeremy Jeffress and Pedro Strop, who re-signed a minor-league pact with the Cubs after being DFA’d by the Reds.


Fortunately, the staples in the Cubs outfield Kyle Schwarber, Ian Happ, Albert Almora Jr. (alternate site) and Heyward remain under team control, but the Cubs grabbed some rentals at the trade deadline.

Almora certainly looks like trade bait, and at age 34, I wouldn’t look for the Cubs to re-sign Cameron Maybin, although he certainly did his best to help the squad. Also up for grabs, is 30-year-old speed-demon, Billy Hamilton. The Cubs could always use speed – Hamilton’s specialty – but his fielding is mediocre and his bat is sluggish (no pun intended) at best.

Cubs Infielders: Time to Deactivate Some of the Inactive

Daniel Descalso (age 34) is one of only two infielders for Chicago who are true free agents this year. The Cubs do have a $3.5M team option on him ($1M buyout), and in my estimation, they can’t scratch the million-dollar check out fast enough. Descalso has been horrific since day-1 and was conveniently buried on the IL this season with one of those ever-nagging phantom injuries.

The second on the list is Chicago area native, Jason Kipis (age 34). Kipnis did relatively well for the Cubs this year, and if he’s willing to play for reasonably small money, I could foresee an extension in his future. Kipnis brings veteran leadership – something the Cubs would lose if they were to part ways with Lester, Rizzo and others.

Being Truly Active is Going to Mean Trades For the Cubs

At this point, anything is possible. Theo Epstein has said that there is no such thing an an “untouchable” player, and after bowing out at the NLWC level (or below) for the past three seasons, nobody’s name in the trade rumor mill would surprise me.

Headlining my list is third baseman, Kris Bryant. KB had a great season in 2016 (MVP), and has been garbage ever since. They should have traded him this season, giving the buyer a season-and-a-half of controllability, but the Cubs hung on, perhaps hoping for a miracle in terms of offensive production. No dice.

Bryant knows he may may very well be on the trade table in a month, as his agent (Scott Boras) is never going to throw a likeable (or affordable) number in Tom Ricketts’ direction. As indicated by the folllowing quote, it appears Bryant is somewhat dissatisfied with the way the Cubs are doing business. You may have to read between the lines a little, but you can decide for yourself…

“The Dodgers are doing all they can to win. They really want to win. That’s kind of admirable. They’re really going for it. They traded away a really good outfielder that really helped their team last year for, what, maybe one year of Mookie Betts? Which they saw as a chance to get them a World Series. Good for them. I wish more teams would kind of follow that in terms of really trying to win and go all-in.” -Kris Bryant

Well, Kris, Justin Turner’s a free agent this year, so maybe you can latch on with the Dodgers, or any one of a dozen other teams looking for a quality third-bagger who slashed a mighty .206/.293/.351 with a .644 OPS. Bryant may have done a little better (or a lot worse), had he not spent nearly half the season on the IL for various injuries and boo-boos.

As for names like Javier Baez, Willson Contreras, Victor Caratini, Nico Hoerner and others, nothing would surprise me at this point. Javy has had trouble at the plate for two seasons now, and with extension talks stalled, the Cubs could do something radical. Interestingly, Contreras and Schwarber have also turned down extension offers from Chicago over the last year.

Changes for the Cubs seem imminent this 2020 offseason, and if they don’t want to be sitting home next October, they must become active participants this winter. Who stays and who goes? Time will tell.

Follow me on Twitter at @KenAllison18 for more of my content! Don’t forget to join our OT Heroics MLB Facebook group, and feel free to join our new Instagram –  @overtimeheroics_MLB, and listen to our baseball podcast, Cheap Seat Chatter!. We’ll see ya there!

Come join the discussion made by the fans at the Overtime Heroics forums! A place for all sports! 

Share this article

Ken Allison is the senior of two MLB Department Heads, as well as a writer and editor for Overtime Heroics. A life-long MLB fan, he's also written for CubsHQ and had the opportunity to try out for the Chicago Cubs in 1986.