Morning Cubs Roundup: Where pitching stands heading into offseason

Craig Kimbrel (Photo by Stephanie Lynn)

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.

Filed under: Morning Cubs Roundup


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  • There will be a lot of talk all offseason of which of the Cubs core players should be traded. To me, the real discussion is which of their two players with real value (Hendricks and Darvish) will be traded. I don't see how keeping them to "continue anchoring the rotation" makes sense if they are anchoring a team that won't win the WS. I bet you could get a lot back if you pair Hendricks with one of the core five. Pull off the bandaid.

  • In reply to cubs09:

    That would be the way to go if they go into rebuild mode, but I don't see that happening this offseason. At Theo's year-end presser he talked extensively about the future. While he didn't give a definite answer he all but said he's going to stay for the last year of his contract and then move on. He will meet with ownership in the next week or two and make an announcement. He talked a lot about transitioning to a new management group.

    If it will be a completely new group, I wouldn't expect (or want) massive changes. Trading long-term pieces with such value as Hendricks or Darvish would really transform the next several years and direction of the franchise, and bring back pieces to be built around going forward. I think decisions like that would be best left to the next management group. If the plan is to promote Jed into Theo's role, then we may see some of those bigger, bolder moves this offseason. I just don't think so. I think we move one or possibly two of the core offensive players and enter 2021 mostly intact and take another swing at the NL Central.

    Theo stated the obvious with Yu and Kyle atop the rotation, and implied Mills and Alzolay have the 4 and 5 slots as their jobs to lose. We'll need a veteran MOR starter and depth.

    It does seem strange to not have much work to do in the pen, but that's where we're at. It's basically already here as we finally start to see some impact arms percolate through the farm.

  • In reply to BarleyPop:

    I suspect it won’t happen. But it should. The best thing Theo could do for the next leadership team is to hand them a farm system loaded with elite talent and a major league team with a low payroll and a ton of flexibility. Hendricks and Darvish are never going to have higher trade value. A win/win trade like the Sox did with Sale and Q a s the way to go.

  • In reply to cubs09:

    Would this front office consider trading either one of those pitchers right now? Darvish started Japanese pro ball in 2005, lots of millage on his arm.

    Cubs have so many other moving parts to figure out in the next year. Is this front office really bold enough to make the big trade, packaging a starter plus one of the core hitters?

    If the Cubs are in the race next year, for the weak NL central. Would the front office actually make the tougher choice, & trade pending free agents? Potential benefit team longer term, by weakening the 2021 team mid-season.

    I still have no idea why the Cubs didn't trade a few veterans over the last two years, as money became tighter it just seems like the obvious answer to the problem.

    Pulling off the bandaid, l would have zero issues with it.

  • In reply to Naujack:

    I understand the desire of some fans to blow the whole thing up and start from scratch. It worked last time, why not do it again? For one thing it's not guaranteed to work, and another is it really isn't necessary. When the Ricketts purchased the team and subsequently hired Theo and Jed, the entire structure of the organization was in shambles and needed to be tore down to the studs. That's no longer the case. The questions going forward revolve almost exclusively with the big-league roster and player talent in the minors. As painful as the last few seasons have been in relation to expectations, when you set aside emotions and take a look at the situation, it isn't all that dire.

    I've been very critical of the FO over the last few seasons. I think their stubbornness and hubris caused us a list opportunity at true greatness. I think many of the non-moves that cost us the opportunity to dominate were because of personal pride and the desire to not admit evaluative shortcomings. That type of personal pride should have no place within a successful executive, and we paid the price.

    But going forward, the situation isn't that bad. We're a large-market team with a solid organizational foundation. We aren't anchored with huge albatross contracts. We have some pitching ready to step in to predominant roles, including possibly a TOR starter and elite closer. The position-player talent is thin at the upper levels, but there is a potential star in Brennen Davis and above-average starters in Amaya and possibly Morel.

    I think people see the core players approaching free agency and think the sky is falling. It isn't. The next few years will sort of be the opposite of the last several, with pre-arb pitching filling key roles and freeing payroll to sign solid position players.

    Some of KB, Javy, Rizzo, Schwarber, and/or Willson will depart. But with our salary capabilities and solid infrastructure, we'll be able to fill the holes and remain upper-level competitive without a complete rebuild.

  • In reply to Naujack:

    I believe everything will be on the table this offseason. They have to explore all options, especially since budgets are going to tight all across the league. Most teams will likely not be adding big ticket items and instead prioritizing young, cheap talent even more than usual, but there may be a few teams with cash on hand who try to take advantage of the situation and try to build a top team. For instance, if the Dodgers fail to win again, might thru go all out while others are pinching pennies?

    Don't think it is likely to happen this offseason though. No player with a big contract is going to have a ton of trade value. This is just not the right time to blow everything up because top prospects will likely not be on the table in negotiations for any player. Teams with vets to sell will likely be better off waiting until the trade deadline at the earliest. By then, everyone will have a clearer picture of finances and how long the pandemic will extend.

  • In reply to Michael Ernst:

    Very true. That league-wide uncertainty with the financial picture going forward could actually end up being to our advantage. The Cubs are at a natural transition point with the pending free-agency of the core players and the expiration of Theo's contract and likely departure. Couple that with the overall uneasiness of an expiring CBA and everything points to shorter deals and a reluctance to commit long-term dollars.

    We'll need stopgap measures to remain competitive until we transition to a new management group. Theo repeatedly mentioned the majority of free agents facing the probability of one-year or shorter-term deals until the financial situation clarifies. That could be to our advantage this offseason.

    Off course the flip side of that is the lost value we can expect when dealing a Bryant or Willson, but I've already written that off as sunk cost. Nothing we can do about that now.

  • In reply to BarleyPop:

    Players are replaceable, Cubs are at the end of a multi-year playoff run with one World Series! It is time to be bold. Lack of action the last two off-seasons, did it help the Cubs? That question might be impossible to answer.

    Before Covid, teams seemed to be holding onto top prospects more then ever before. Isn't that one of the reasons why no one was traded last off-season from the core?

    Hopefully the Cubs have payroll flexibility after the 2021 season.

    Cubs might not have any money, but they need to figure out a way to maximize the return of controllable assets while they still control them in 2021. Next season, Cubs could maximize the return by actually trading more, or all pending free agents.

    I know fans love Rizzo! Why not trade Rizzo mid-season 2021, & get some controllable assets first. Then offer him a contract after the season If the Cubs want him back.

    Yankees in 2016 traded 3 players and got 11 controllable players/prospects in return. Cubs won't end up with high ranking prospects like Torres, or Frazier. Adding volume of controllable assets during a single season should help the future. Cubs front office has a solid track record with secondary pieces that helped the team when trading veterans.

    Just an idea, & really not creative or original.

    BarleyPop, I absolutely agree, and think this Cubs front office falls in love with certain players. It hurt the run. Cubs traded for Lastella, but never gave him a real chance to be part of a platoon lead-off hitter. I don't want to hear about defense. Inferior hitters were given plenty of opportunities again and again to lead off.

  • In reply to BarleyPop:

    Theo's already missed the value window on especially Bryant and Schwarber. Yu's value may never be higher. If he could have his pick of prospects, Theo needs to just go for it. Being too precious with his core group has just not worked. And refusing to see that a low contact high K group would suddenly change their stripes was a mistake. And on another note, if he can find the money, he could reverse his worst trade and sign LaMahieu.

  • In reply to Michael Ernst:

    The unwillingness to spend is what makes Hendricks so appealing. $14m a year for a 2, borderline 1. For win-now teams like Atlanta and San Diego, I could see that being very appealing.

  • In reply to cubs09:

    It’s no secret on this site that I’ve probably been Yu Darvishs biggest fan and defender over the years. That’s not meant as an arrogant statement it’s Moreso meant as a defense of my perhaps unpopular opinion that you have to trade him within the next 1.5-2 years. Darvish has proved himself to me and in a perfect world I’d love if he were a cub for the next 10 years. But he’s almost 35 years old and I believe that his remaining peak years simply don’t fit the cubs window of contention anymore. Right now the price of starting pitching is as high as ever after Cole signed for $330 million. Darvishs remaining 3 years $60 million is an obvious bargain with how he’s been pitching the last 1.5 years. IMO he’s the best trade chip the cubs have and he’s their best shot at obtaining another teams top prospects. Personally I trade Darvish over Hendricks, because I think Hendricks style of pitching will age well. Hendricks is also a great teammate and face for this organization. Theo said a lot of young cubs pitchers look up to Hendricks as a resource for pitching and being a good professional.

    The one issue is Darvish I believe has a no trade clause through year 4. To me they have to trade him before he begins to show physical related decline. I think Yu may well pitch at a high level over the remaining 3 years of his deal. But I wouldn’t take that chance if I were the cubs. To me Darvish is the new Jeff Samarzija or Matt Garza. He’s the best trade chip to spearhead the next generation of young cubs talent, and they have to trade him while his value is high. I imagine every contender in the league can use a pitcher of Darvishs caliber, and I don’t accept anything less then a rick package of prospects.

  • I like Lester. He is a big game pitcher. However, I'm not sure that smoke and mirrors will be enough going forward. He looked heavy this year, both his face and uniform filled out in 2020. I don't want to disrespect Big Jon, but I would like to see him work out and lose a couple pounds over the off season. He might find that old edge return.

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    I believe the cubs have to move at least two core players and one starter, the core players to move would be Baez, Bryant or Schwarber, 2 of the 3. The only way I keep the starters is if the cubs could get Bauer to join the staff. With a trio of starters like that we could pick up some interesting players from our two moves of core players, say Brantley and LeMahew( not sure) ,and still contend.
    We are a long way away getting our minor league into a top ten, Epstein and Hoyer both have to go in my opinion, this year if possible. I would scour the padres, yankees rays and braves organization for the best young executive and give them free reign .

  • Agree the virus will drive the trade market and free agency. Ownership will go with “cheap” players over increasing payroll. The virus may come to an end next season but then you are looking at a new CBA and most likely a strike following. So with this concluding season and next two looking very bad no way trades and spend help this club. Only thing we can hope for having a great season next year is players motivated by free agency money.

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