Presented By Cubs Insiders

The offseason is officially upon us, free agency kicks off Friday afternoon and the central focus in Cubdom is on the 2019 squad.

But what does that roster look like at the moment?

Brandon Kintzler is back after exercising his $5 million player option. Jose Quintana is back after the team picked up his $10.5 million option. 

As of this writing, Cole Hamels and Pedro Strop have not yet returned to the club in an official capacity as the Cubs haven't picked up their options (though both are expected to return for 2019 some way, some how). 

The Cubs' list of free agents isn't particularly bothersome, as Daniel Murphy and Justin Wilson are expected to leave and sign elsewhere. The Cubs still may bring back veteran pitchers Jesse Chavez, Jorge De la Rosa and Jaime Garcia, but that trio looks set to at least hit the open market this weekend.

Of course, then there's the rest of the free agent market that includes such names as Bryce Harper, Manny Machado and Josh Donaldson. Plus, any potential trades that may happen this winter that would affect the blueprint of the 2019 squad.

Here's how the Cubs' 2019 roster looks today:


Willson Contreras
Victor Caratini

One of the underrated areas where the Cubs could improve this season would be a reliable, veteran backup for Contreras. The organization and coaching staff like Caratini a whole lot, and the pitching staff seems to trust him more and more by the day. But he also has only a .238/.303/.317 slash line in 266 big-league plate appearances and that lowers to a .214 average and .268 slugging percentage against left-handed pitchers. 


Here's the Cubs' current list of depth at catcher beyond these two guys:

Taylor Davis

That's it.

The Cubs will want to keep Contreras fresh in 2019 after he caught far and away the most innings in baseball this past season - an issue that undoubtedly had some sort of effect on his low offensive/power output. 

Look for Theo Epstein's front office to make a move or two to at least add depth to this position group over the winter.


Anthony Rizzo
Javy Baez
Kris Bryant
Ben Zobrist
Addison Russell?
Tommy La Stella
David Bote

Zobrist can fall under either infield or outfield, but we're gonna include him here simply because this current roster needs an everyday second baseman and he's the best option to fill that void at the moment. 

Russell is a major question mark given the organization has yet to make public their determination on where the embattled shortstop fits in the team's future. Does the domestic abuse suspension create a situation where Epstein and Co. get rid of Russell and start fresh? If Russell is still with the team come Opening Day, he will still be suspended for the first month at least. 

Bote has worked his way into a utility role, at the very least. His flair for the dramatic and his stellar defense will keep him in the big leagues for good next year and Joe Maddon has already talked about getting Bote some work in the outfield this spring to be a backup at every position but pitcher and catcher in 2019.


Jason Heyward
Albert Almora Jr. 
Kyle Schwarber
Ian Happ

This is the area where we could see the most change between now and the day pitchers and catchers report to Mesa, Arizona. Could it be Harper? Could a Machado or Donaldson signing push Bryant to the outfield full time? Could the Cubs trade away Schwarber or Happ or Almora?

There are far more questions than answers with the structure of this group at the moment, but even if it does remain intact, there are plenty of questions about the production of this unit as well. 

Can Schwarber take that next step as one of the most feared sluggers in the game? Will he be able to maintain the jump in defensive metrics we saw in 2018? Will Happ regain his power stroke and cut down on his strikeouts while still walking at an elite clip? Will Almora hit righties or slug enough to warrant everyday consideration in center? Can Heyward continue to be roughly a league-average hitter to go with his stellar defense and clubhouse leadership?


Jon Lester
Kyle Hendricks
Yu Darvish
Jose Quintana
Drew Smyly

Epstein said Smyly will be stretched out as a starter in spring training as the left-hander is working his way back from Tommy John surgery. Even if he ultimately doesn't find his way into the rotation, he has a strong resume as a relief pitcher in the big leagues and is great depth in case a starter or two go down to injury.


This position group is also expected to add Hamels, which could be the impetus behind moving Smyly to the bullpen. Tyler Chatwood and Mike Montgomery (more on them later) figure to be relievers unless injuries befall the rotation in spring training or Chatwood somehow convinces the Cubs he has suddenly rediscovered his command.

Lester, Hendricks and Quintana are stalwarts of this unit with Darvish expected to make a full recovery from the elbow/triceps issues that limited him to just 40 innings in 2018. Could Darvish actually be the freshest pitcher of this group thanks to almost an entire year off to heal and save some bullets? It's possible. Don't forget this is one of the best strikeout starting pitchers the game has ever seen.


Brandon Morrow
Carl Edwards Jr.
Mike Montgomery
Steve Cishek
Brandon Kintzler
Brian Duensing
Randy Rosario
Tyler Chatwood

Strop will find his way into this group eventually, which really helps boost the overall strength of the bullpen. Still, the Cubs figure to provide some reinforcements via free agency or trade over the offseason. At the very least, they need more quality depth and at most, they need a reliable closer that can push Morrow more into a low-key setup role where Maddon and Co. can make sure his workload is limited.

Duensing was very good in 2017, but struggled for most of 2018 as he dealt with a shoulder issue. Rosario showed flashes as a rookie and Cishek was the MVP of the bullpen for 90 percent of the season. Kintzler had a long history of success as a high-leverage reliever before coming to the Cubs and Edwards still possess the best pure stuff of anybody in this bullpen. But every one of those guys has a major question mark hovering over them. 

Chatwood doesn't seem to make a ton of sense in a bullpen that only has 8 options given his lack of command, but unless the Cubs can unload him this winter, he'll be on the team in some capacity. He's owed $25.5 million still, so the Cubs would have to eat a large chunk of that if they were to deal him away this winter.

Will Montgomery be OK swallowing his pride and once again being utilized as swingman that most likely starts the season in the bullpen? He was very outspoken last year about how badly he wanted to be a starter.

The Cubs could do well for their bullpen if they opt to bring back Chavez and De La Rosa on short-term deals. Both veteran journeymen provided a boost down the stretch.

The Cubs have some OK depth beyond the aforementioned bullpen, with Alec Mills, Duane Underwood Jr., Allen Webster, Dillon Maples, Jerry Vasto, James Norwood and Justin Hancock all under team control for 2019. 


And that's saying nothing about the organization's top pitching prospect (starter Adbert Alzolay) or young pitchers who have yet to make their MLB debut but have had varying levels of success throughout the Cubs system (Oscar De La Cruz, Trevor Clifton, Alex Lange, Brendon Little, Dakota Mekkes, Bailey Clark). 

Mekkes, in particular, is an intriguing option and could be on the verge of joining the big-league bullpen after posting a 1.17 ERA, 1.21 WHIP and 11.9 K/9 in 41 games between Double-A and Triple-A. 

Mills may be in line for a bigger role in 2019, as well, after impressing in 7 games in the majors (4.00 ERA, 1.00 WHIP, 23 K in 18 innings). The Cubs liked his stuff and presence in his late-season audition and he's still only 26 (turns 27 later this month) and under team control through at least 2023. 

Still, the Cubs will need to address the bullpen with multiple additions this winter to ensure they don't fade down the stretch for a third consecutive season.