Craig Kimbrel (Photo by Stephanie Lynn)

Cubs Current Roster

Earlier this week I examined the Cubs roster from a position players perspective heading into the offseason. Now it is time to turn to the pitching side. As with the original post this won’t be a full deep dive into every potential scenario but rather a high level overview. This is going to be a crucial offseason for the Cubs in determining whether they can remain atop the NL Central in 2021 or if a step back to remake the roster for greater long term success is necessary.

Thankfully, the organization is in better shape pitching wise than it has been in quite some time. They have little money committed long term and a handful of prospects who appear ready for MLB jobs in the near future. While that may not offer much security it does provide them with flexibility. And despite every qualm over the last five years that a lack of pitching was going to be the organization’s downfall, the front office has managed to piece together playoff caliber rotations and bullpens every year (with the exception of 2019 when late inning relief failed).

Starting Rotation

40-Man Roster (8): Kyle Hendricks, Yu Darvish, Adbert Alzolay, Alec Mills, Colin Rea, Brailyn Marquez, Tyson Miller, Justin Steele

UFA: Jose Quintana, Tyler Chatwood, Jon Lester (Cubs will decline his $25M option and instead pay $10M buyout)

Rule 5 Eligible: Cory Abbott, Keegan Thompson, Duncan Robinson, Brendon Little

It sure is nice having Kyle Hendricks and Yu Darvish locked up on good contracts to continue anchoring the rotation as the Cubs enter a transition period.

After enjoying rotation stability thanks to a lot of money directed to a lot of veterans over the years the Cubs will enter 2021 on a little less stable footing. Three big contracts are coming off the books, and while the Cubs may end up bringing one of them back, it will be at a reduced salary and likely on a short term deal.

The sentimental favorite to return is Jon Lester. He may be running out of gas, but he still rises to the occasion often enough where a one year deal isn’t out of the question. Jose Quintana offers perhaps a wiser investment however. He’s five years younger, has been a consistent innings eater who never misses a start (freak household accident aside). His arm is not what it was in his prime, but it is healthy. I wouldn’t be shocked if Q would also accept a one year deal in an attempt to rebuild his value and re-enter free agency next year in a hopefully-non-pandemic market. A modest 2-3 year deal would also be possible.

Whether the Cubs re-sign an incumbent or choose to go outside the organization, they will surely add at least one veteran starter through trade or free agency this offseason. The Cubs have entered every season for the past five years or so with a pretty clear cut top seven starting pitchers identified. Sometimes all seven make the 25-man roster with the two extras being used in swing roles, but most times the club has a single swing starter in the MLB pen and then another option fully stretched out in Iowa. Expect 2021 to be no different.

Once a third veteran is secured to slot in behind Hendricks and Darvish, it will be interesting to see how the Cubs handle the back end of their rotation. Adbert Alzolay will receive on of the two slots. He’s healthy, he added a potentially devastating slider this year, and he’s out of options in 2021. It’s time.

The fifth slot could remain in the hands of Alec Mills. The front office and coaching staff have spoke often of their faith in him this season. While he was homer prone and vulnerable to left-handed batters, he was basically a league average starter. That’s perfectly acceptable for a 5th starter, especially one who won’t even reach his arbitration rights until next offseason. I still think Mills is best suited to the swing role which he actually occupied this year prior to Q’s injury, but with the budget likely tight once again, Mills does offer a low cost rotation option next year.

If Mills does remain in the rotation the Cubs will need to identify a new swing man. Colin Rea looked good in one inning stints this summer but struggled when asked to extend further. Tyson Miller also received a cup of coffee this year. Justin Steele offers another internal option. I think it more likely Miller and Steele open 2021 in Iowa, but it will depend how willing the Cubs are going to be to trust their prospects. They’ve been loathe to do so in recent years, but at some point the Cubs are going to have to give young players a shot. Easing a young guy in with the swing role is one way to accomplish it.

The Cubs will add Cory Abbott to the 40-man this offseason and he figures to battle with Rea, Miller, and Steele for any swing and Iowa rotation depth roles. Keegan Thompson and Duncan Robinson will likely enter 2021 as the top non-roster depth in Iowa’s rotation.

The wild card is Brailyn Marquez. He struggled with his control in his MLB debut on the final day of the regular season, but he’s the type of prospect who an org makes room for at the MLB level once he is ready. It is highly unlikely that occurs at the start of next season. In fact, Marquez may open in AA, where he was projected to start this year. But again, he’s the type of talent that can make the jump at any time. If it happens sometime in 2021, that’s should be considered and unexpected bonus, but the Cubs can’t count on it happening.

Right Handed Relievers

40-Man Roster: Craig Kimbrel, Rowan Wick, Ryan Tepera, Jason Adam, Dan Winkler, Duane Underwood Jr., James Norwood, Dillon Maples, Manuel Rodriguez

UFA: Jeremy Jeffress

Rule 5 Eligible: Michael Rucker, Dakota Mekkes, Trevor Megill, Erich Uelmen

This group is pretty self explanatory as the team has basically the same group that came together and did a pretty damn good job down the stretch under contract for next season. I suppose the Cubs could try to re-sign Jeffress, but they need to be careful to not strangle their roster flexibility by having too many relievers on guaranteed deals who can’t be optioned to the Minors. That was their mistake in 2019.

There will be some movement in this group though. Dillon Maples will be out of options, so the organization has reached a decision point with him. It is difficult to envision him earning a MLB job out of spring training next season. I also expect the team to add at least one of Michael Rucker, Dakota Mekkes and Trevor Megill to the 40-man this offseason. Rucker reportedly had a good summer, and given he was picked in the Rule 5 draft last winter it would seem prudent to protect him this time around. He offers mid-90s velo in a four pitch mix.

The Cubs have done a good job identifying undervalued arms from other orgs the past couple of years and then building them up enough to wring good value from them in the MLB bullpen. I expect the Cubs will maintain that same approach this winter. Rather than re-signing Jeffress, I expect them to try and identify the next Jeffress for Hottovy and the rest of the staff to work with.

Left Handed Relievers

40-Man Roster: Kyle Ryan, Brad Wieck, Rex Brothers, Justin Steele, Brailyn Marquez

Free Agents: Andrew Chafin, Josh Osich, Matt Dermody, Danny Hultzen, Jerry Vasto, Jordan Minch

Rule 5 Eligible: Wyatt Short, C.D. Pelham, Bryan Hudson, Brendon Little

Non-Roster: Burl Carraway, Jack Patterson

This is the area I am going to be fascinated to see how the Cubs approach this offseason. Their primary incumbent Kyle Ryan fell off in 2020, and while Brad Wieck and Rex Brothers are talented, they cannot be considered reliable options heading into 2021. I can envision all three entering spring training on the 40-man but I can’t see more than two entering the regular season on it. Ultimately, there may only be room for one, so they’ll need to be at their best in Mesa.

The situation cries out for a proven lefty reliever. I think Andrew Chafin may end up being that guy. At least as a fallback. I can see the Cubs pursuing an upgrade through trade or the early portion of free agency, but if they are unable to make a deal, they could re-sign Chafin. Even if they do bring in a different arm through UFA/trade, they could still bring back Chafin and move on from Kyle Ryan instead.

What makes this situation even more intriguing though, is that for the past several years, left-handed relief has been perhaps the weakest portion of the Cubs farm system. They had nothing in the upper levels, forcing the Cubs to bring in a ton of arms from outside the org in an attempt to find a solution. Some worked (Ryan, for one) but most didn’t.

Now though, the Cubs actually do have young power arms percolating toward the Majors in 2021. Justin Steele may enter 2021 stretched out as a starter, but the bullpen will be his MLB role, at least initially. And while I project Brailyn Marquez to the Cubs rotation in 2022, there is no question he could help the Cubs out of the pen in the 2nd half of 2021 should they need him.

The Cubs have the luxury of two additional lefty relievers capable of helping next season who they do not even need to protect from the Rule 5 draft. Burl Carraway was the Cubs 2nd round pick this past summer and he possesses a special arm. Capable of reaching the upper-90s, he backs it up with a hammer curve ball and apparently has shown some feel with a slider and/or changeup as well. He is a potential elite reliever who can be used in any situation from fireman, to the 8th or 9th inning.

Carraway and Marquez will get all the press, but keep an eye on Jack Patterson next summer. He possesses a bowling ball sinker and a starters arsenal of secondaries. The Cubs may in fact envision him as a starter long term, but there is also a good chance he could serve as a groundball specialist (who can also miss a few bats) or even as a swing option in a Major League pen as soon as the 2nd half of next season.