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Cubs: Assessing the Offseason Outlook, Difficult Decisions Ahead

The Chicago Cubs have some work to do this Winter to get back to the World Series, here's a look at some of the difficult decisions ahead of them.

With the GM meetings well underway it’s an appropriate time to examine the Cubs’ roster needs and potential targets via free agency and trades – with a spattering of speculative thought. I won’t make any bold claims here, nor will I assume I know what the hell is going to happen. Rather, I’m providing my best guess(es) given the circumstances of the team, the climate of the free agent and trade markets, and the track record of Theo Epstein and Jed Hoyer.

Regardless of what happens two things are certain: 1) the Cubs will be quite active during the hot stove season, and 2) watching this madness unfold across MLB is going to be a lot of fun. Let’s get started.

Roster Overview

The 40 man roster currently sits at just 33 players, providing plenty of flexibility and creativity for the front office. This means the Cubs should be able to fill their roster needs without putting anyone in DFA limbo or exposing a youngster to the Rule 5 draft. And given the number of holes they need to fill on the roster this is a very good thing, indeed.

The laundry list of roster holes remains disturbingly long, however, with several players departing for free agency (most of which are entirely unlikely to return). These departures leave the Cubs needing two starting pitchers, a backup catcher, at least two (preferably high leverage) relievers, and a backup outfielder. Let’s look at these in order.

Starting Pitching

Much has already been said about what the Cubs should do with the 40 percent void in the rotation. Everyone seems to be convinced that Jake Arrieta will not be returning, as he is seeking a seven year contract with an AAV commensurate with his Cy Young campaign of 2015 and second half of 2017. With the Cubs having plenty of youngsters that are or will soon be hitting arbitration, shelling out a huge contract to an aging starting pitcher doesn’t make a whole lot of sense.

That last bit is precisely why I don’t believe the Cubs will be pursuing Yu Darvish for the contract he’s seeking, either. Paradoxically, however, the baseball world seems to think that Darvish will become a Cub, with a contract greater than that of Arrieta. Even MLB Trade Rumors (one of my favorite baseball sites) has become a victim of this flawed reasoning, suggesting that the Cubs will ink Darvish to the tune of six years, $160 million while letting Arrieta sign elsewhere for four years, $100 million. Incredulous, I am, and I’ll eat my hat if the Cubs overpay for Darvish while Arrieta signs for just four years.

Photo: Jonathan Daniel – Getty Images North America

I’m not saying the Cubs absolutely will not sign Darvish, I just don’t think they will put that much money into an injury prone pitcher if a known commodity to them (and fan favorite) can be had at a much more reasonable rate. The Cubs will resign Arrieta if he ends up getting a four year deal. And they’ll be active bidders for Darvish, but ultimately passing on him if he gets six years.

That still leaves one rotation spot open. The obvious fit here is Alex Cobb, who would be reuniting with his long-time pitching coach, Jim Hickey. At 30, and with some injury history, there are concerns regarding his durability (he has yet to approach 200 innings in a season). His second half this past season was quite encouraging, however, and the expected contract ($48 million over four years) is quite palatable. Even though he carries draft pick compensation along with international money from turning down a qualifying offer from the Rays, he’d fit quite nicely at the back end of the Cubs rotation. This is as much of a no-brainer as there could be in free agency. That doesn’t mean it’ll happen, but if I bet on one free agent the Cubs land, I’d bet on Cobb.

There are, of course, other free agents available, but none of them seem to fit the Cubs to the same degree that Arrieta and Cobb do. Lance Lynn is a known enemy commodity, with a similar career trajectory as Cobb’s, and for that I think the Cubs will be in on him. CC Sabathia had a solid season, but doesn’t seem like a logical fit – nor does it seem likely he’d make his way to Chicago at this stage of his career. I remain convinced the Cubs will go after Cobb aggressively, and if Arrieta’s asking price drops as the off-season wanes? The unlikely reunion may happen after all.

There are also in-house options – most notably Mike Montgomery – but these seem too far-fetched at the moment. It’s clear the preference is to keep Monty in the bullpen (and the de facto #6 starter) but it wouldn’t be entirely shocking to see him crack the rotation should the market not develop the the front office’s liking. There are also some dark horse candidates, such as Eddie Butler, Alec Mills, and Jen-Ho Tseng – but these all seem like depth pieces for now that may or may not make an impact in 2018.

Finally, there’s the trade market, with the noted admission from Theo that they are willing to trade position players on the MLB roster for the right young arm(s). Though it’s hard to speculate what this might mean given the opaqueness of the current free agent landscape, it’s not impossible to see the Cubs dealing away one of Kyle Schwarber, Ian Happ, Javier Baez, or even Addison Russell. When the free agent dominoes start to fall this will become more clear, and if Theo and Jed find a deal to their liking don’t be surprised if they pull the trigger on a blockbuster.

Backup Catcher

The trade for Alex Avila (along with Justin Wilson) turned out to be a fantastic move down the stretch, as he filled in capably for the injured Willson Contreras and provided much needed depth upon his return. Coming off a career year, however, and with no qualifying offer attached to his name, Avila is likely to get a nice contract that will afford him the lion’s share of starts behind the dish. This eliminates him from a return to the Cubs.

Thankfully, there is a clear answer to this void, as Victor Caratini appears ready for the bigs on a full-time basis. A switch-hitter with acceptable defense (and the versatility to back-up Anthony Rizzo at first) he’s a solid compliment to Contreras. Don’t expect the Cubs to get creative here: I’m confident Caratini will be the back-up catcher in 2018.


With Wade Davis departing for free agency, our only reliable relief arm in the playoffs (all due respect to Brian Duensing, who’s also a free agent) is no longer on the roster. While there were hopes Carl Edwards would prove ready to become the closer in 2018, he fell apart during the playoffs – in a manner as ugly as it was untimely. While I have all the faith that Edwards will re-establish himself as a high leverage arm, it would be foolish (at best) to hand him the closer’s job.

Wade Davis #71 of the Chicago Cubs pitches in the ninth inning against the Los Angeles Dodgers during game four of the National League Championship Series at Wrigley Field on October 18, 2017 in Chicago, Illinois.

Justin Wilson will be back, and aside from his atrocious walk rate with the Cubs (he was left off the NLCS roster after being traded for as a playoff piece!) he’s proven to be a fantastic reliever with closing experience. Expect his role to be a 7th/8th inning guy – but he will not be our closer. There’s also a potential hidden gem in Randy Rosario, a hard-throwing lefty the Cubs claimed from the Twins. It’ll be interesting to see how Hickey works with him, and what potential role he could provide next year.

Bottom line is this: The Cubs need Davis, and I think we’ll see them pursue him aggressively. Not all closers have consistent careers, and not all of them age gracefully. But a three or four year deal for Davis would be a reasonable move to make, and if they can get him for a lower AAV than last year’s trio of closers – when he’s every bit as good – it’d be a bit of a steal.

As for Duensing, who resurrected his career in Chicago, a reunion would also be welcome. Maddon trusts him (to a degree) and he’s proven to be an effective and versatile arm. I’d like to see the Cubs resign him if the price is right, but it’ll likely take some time to see what his market price will be.

The bottom line is that the bullpen has to get better than it was down the stretch and in the playoffs. The good news? Aside from a closer the answer(s) to this problem might already be in house. While the walks must be addressed, the bullpen had one of the lowest ERA’s in the NL last year, and still employ several talented arms. We need reinforcements for the bullpen, not a dismantling of it.

Backup Outfielder

I am entirely convinced Jon Jay will not return to the Cubs. And while this pains me – he’s one of my favorite players – I understand why considering he’ll likely get an opportunity to play every day next year, something the Cubs simply can’t offer him. With Albert Almora emerging as the every day center-fielder, Ian Happ, Kyle Schwarber, and Ben Zobrist maintaining an awkward timeshare in left field, and Jason Heyward‘s perfect defense (and ginormous contract) in right field – there’s no room for one of the most underrated players in the game.

A trade could change all of this, of course, and with Jay expressing his love for Chicago, a reunion isn’t altogether impossible. I don’t envision the Cubs being active shoppers for a reserve outfielder, but if Jay continues to languish without a job, and one (or two) of our young position players are traded away, we could see a reunion. Short of that, I imagine the Cubs will roll with the current outfield alignment as it is, leaving Joe Maddon to figure out how to get everyone playing time.

The Shohei Ohtani Question

There’s no need to speculate too much on Ohtani – especially when our very own Matt Grabianski covered his fit with the Cubs extensively. It would be highly entertaining to see how Maddon would employ him, he would kill two birds with one stone (as the kids say), and, well, it’d be a lot of fun to see him in a Cubs uniform. But this is perhaps the most unique and convoluted player contract situation in baseball history. To suggest what might happen would be foolish.

Final Assessment

As stated earlier, the Cubs are going to be active – both in free agency and exploring trades. There will be rumors galore, some of which will have merit while others will be silly (Heyward to SF?). The good news is that the Cubs have some in house options, the ability to spend on the right free agents, and position player depth to make a trade for a controllable SP viable. It’ll be a fascinating ride, for sure. Let’s hope we arrive at a happy destination.


Austin is the Lead Cubs Writer for The Loop Sports. He's a lifelong baseball junkie (due to his father) and as a former college pitcher has a particular affinity for the art of pitching. Austin loves to commute in Chicago on his bicycle, and enjoys camping and canoeing as often as possible. He attained his master's degree in Social Justice and Community Development from Loyola University Chicago in 2014.

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