Early Offseason Primer: A 6-Item Checklist for Bringing Cubs Another Title

The baseball postseason is now past the halfway mark and the Cubs haven’t played in well over two weeks. Which means if you and the Cubs fans in your life are as passionate as those in my life, you’ve already heard trade and acquisition suggestions that would combine to turn over two-thirds of the major-league roster.

As for my own offseason contemplation, I usually take a two-step approach. First, I have few sacred cows. My list of untouchables is usually the shortest around as I subscribe to Theo Epstein’s approach to always listen to any offer for any player without a no-trade clause.

Second, I like applying strategic rigor to this exercise. Being in a championship window means every move must improve playoff-win probability. If a move doesn’t nudge that needle, it’s a non-starter. So while Bryce Harper would make watching 162 regular season games more entertaining, recent analysis shows him adding only marginal playoff value.

With this in mind, here is my six-step road map for returning the Cubs to baseball’s premier pedestal.

1) Luxury-tax decision

CI’s Moshe Wilensky covered this exquisitely earlier this month. When you add up current 2019 payroll obligations, arbitration increases, and just replacing expiring contracts, it seems impossible to come up with a realistic scenario for contention that doesn’t blow past the luxury tax cap for at least 2019.

Good news is once you make this decision, it opens up a lot of options for the Cubs.

2) Diversify the offense

After 2017, Epstein identified flaws in the Cubs offense, but then rolled the dice on another year of maturation and development for the same group of free-swinging, high-strikeout young hitters. Only Javy Baez improved. However, even he showed the same deficiencies against power pitchers, and quality finesse pitchers still could  get most of the offense to chase outside the zone.

So my key word for improving the offense is “diversify.” This team cannot make additions – *cough* Harper *cough* – that just replicate its young hitters’ existing strengths and weaknesses. The two best ways to diversify is to add hitters who produce well against power arms and/or are legitimate stolen-base threats who can pressure pitchers even when bats slump.

This is why I thought someone like Lorenzo Cain would have been ideal for the Cubs. After all, who wouldn’t want a proven gamer who hits power pitchers, is still a stolen-base threat (31 in 2018), can play great defense in center, and is a David Ross-style leader who brings the daily urgency to games Epstein says he hasn’t seen since 2016?

Sadly, this year’s free agent crop features no Cains. But free agents like either Manny Machado or Adrian Beltre – one young and one old, one very expensive and one not so much – would certainly bring quality at-bats against power arms. The Cubs could then trade for a speedster, such as Kansas City middle infielder Aldberto Mondesi (32 steals in 75 games) or Tampa outfielder Mallex Smith (40 steals).

3) Solve the shortstop situation

Many fans would prefer to limit the choices to Machado or Baez. Personally, I wouldn’t bet on either as Epstein’s Plan A. Why not? Because he has a long history of appreciating quality defense over offense at short.

Consider his final big roster move to end the Red Sox’ title curse in 2004. He traded the offense of Nomar Garciaparra for the Gold Glove of Orlando Cabrera. Then seven years ago, he (correctly) saw neither Starlin Castro nor rising prospect Baez as his shortstop answer. So Epstein traded for what critics considered a talented but redundant talent in Addison Russell because he knew the importance of Russell’s superior glove.

Now with Russell’s off-field issues, Epstein faces the same question again. So I don’t see him suddenly changing philosophies since the shortstop position is just too important defensively.

This leaves trade and free agency as the team’s options. Some have floated free agent Jose Iglesias, but my jury is still out on his defense. Another option is to start the season with either Baez or Machado at short, but with the plan to upgrade defensively later on. This could be via trade or if – and it’s a big “if” – Russell somehow climbs that steep hill and reclaims the faith of his teammates and the organization.

4) Add a dominant back-end reliever

Ideally you want three strong back-end relievers to win a World Series. The Astros last year and the Cubs in 2016 narrowly got by without this. However, both had superior starting staffs, which the Cubs may not have in 2019 even with a full rebound by Yu Darvish.

This means the Cubs must add another high-end reliever, preferably with closer stuff. This would allow them to spell Brandon Morrow with someone other than just Pedro Strop while alleviating Joe Maddon’s temptations to over-use his closer. Same goes for not stretching the not-quite-rubber-armed Steve Cishek to his breaking point.

5) Better backup catcher

If the goal is increasing playoff-win probability, having a better rested Willson Contreras for the playoffs is critical. If the Cubs brain trust doesn’t trust Victor Caratini to start 40-50 games behind the plate next year, they must move him and get a solid backup. And even if salary cap considerations will not be an issue this year, it’s worth noting that the Brewers got Eric Kratz from the Yankees for next to nothing in trade and salary.

6) Diversify the rotation?

Even with Darvish’s injury and Tyler Chatwood’s, uh, Chatwoodiness, the rotation remained the team’s best pole-to-pole unit. Presuming the Cubs at least pick up Cole Hamels’ 2019 option, this would make Hamels and Jose Quintana the team’s Nos. 4 and 5 starters. For me, that pushes the rotation far down the list of pressing issues.

That said, there’s still a discussion to be had. Whether the Cubs have Hamels or Drew Smyly in the rotation, they’ve got three lefties with fairly similar repertoires. If either Hendricks or Darvish goes down, that means going with the same type of pitcher three times in a five-game playoff series and up to five times in a seven-game series. This would seem a competitive disadvantage for the Cubs.

So the front office should at least weigh replacing either Hamels or Quintana. And replacing Quintana would give the Cubs an extra trade chip to address other needs. They could kick the tires on free agents. Patrick Corbin will be the “it” free agent pitcher, but the lefty is probably not different enough in style.

Or they could get creative in trade. With the Diamondbacks in rebuild mode, Zack Greinke and his remaining $105 million over three years will be available. You wonder if Ian Happ or Albert Almora Jr. and an A-ball prospect would be enough to get Greinke (who has a limited no-trade clause), provided Arizona kick salary relief including taking Chatwood’s $25.5 million.

There you go. A simple six-step to-do list, each item of which has an eye toward improving playoff-win probability. Of course, nothing is ever so simple. Take three winters ago, when the Cubs prized Arizona’s base-stealing, Gold Glove-caliber center fielder Ender Inciarte. Unfortunately, Arizona coveted young pitching and vastly overpaid to get Shelby Miller.

Arizona sent Inciarte and that year’s No. 1 overall draft pick, Dansby Swanson, to Atlanta. The Cubs re-signed Dexter Fowler during spring training when a deal with Baltimore fell through at the last minute. Fortunately, it worked out for the Cubs in 2016. Here’s hoping the same happens in 2019.


  1. I’m a huge fan of Mallex Smith. The speed alone is drool-inducing, but that OBP at the top of the order?? Yes please.

    Problem is, I have a hard time seeing the Rays trade him to the Cubs.

    1. Availability and both teams being a good trade matches are always issues. Which players to target will also be informed by other off-season decisions. For instance, if Machado isn’t signed, getting Merrifield and playing him at second is more of an option. (I don’t see his SS defense as good enough.) Or if Bryant doesn’t stay at third, the outfield gets crowded and Mallex Smith may be less probable. It will be interesting to see how Theo/Jed work the off-season puzzle.

      1. It’s odd – we want the Cubs to hit more home runs yet we talk about guys like Merrifield and Smith who lack power. But I get it – those are team needs, as you said – something different from what already exists.

        I wonder what will become of Addison Russell. I’d love to see the Cubs DFA him, but I think you mentioned it in an earlier post, why leave him available for the picking for the Brewers or Cardinals?

        Trading Quintana could save them his $10.25M option. That wouldn’t be a bad thing if you keep Hamels, but then you basically gave away Jiminez and Cease for two years of inconsistent starting pitching. So many tough decisions. Sometimes you have to bite the bullet and hope something different works I guess.

        1. Yeah I think, w hindsight bias, we’ll look back and say the Cubs basically gave away Eloy/cease. Keith law thought it was a decent move at the time (and had Q in his top 15 pitchers). It just didn’t play out. Hes def a redundant type arm, not sure what to do.

          With the shifting, ground balls (esp from left side) from slow runners are outs. So either stick your team w line drive/fly ball hitters, or swap out a few of the guys for contact speedsters, and live w 160-190hr p year. Slow ground ball hitters is death.

          The best biz move on addy of course is to sign and trade, he’s a 3-4 War SS. Is that unethical?

          1. Quintana will never be elite with only two pitches. I wonder if the Cubs thought he would have had a third pitch develop? Now Q COULD be a lights out reliever. Add a couple ticks to that FB because he is pitching in short spurts and he could be elite. Not sure he has the mentality to do it, nor do I think he has the pace between pitches.I do think if he would have been a reliever to start with he would now be an elite closer however.

          2. It’s kinda strange. The guy was a legit #2 for 4 years. (W a bad defense behind him). I remember him having a great curve, w good command. He’s looked so pedestrian in a cubs uniform. Healthy LH starters are so valuable, tough to see move to the pen. Cubs could trade him, but not sure they much more than the salary. He’s very CC sabathia, and he gets 1 year deals for 10M. Maybe more bc he has 2 years of control and is healthy, but I like the idea of moving him for positional help. Hamels, Lester, Montgomery, smiley, Q. The whole rotation is lefties, and none are power pitchers (by today’s standard).

          3. It’s odd because when he’s on, even with two pitches, he’s dominant. I’m sure the Cubs will keep him. He’s not going to develo that third pitch though.

          4. This is a nice string / good conversation!

            I think the challenge for Q is that none of his (2-3) pitches are ++, and most games he simply has a hard time putting guys away. I wasn’t a fan of that trade when it happened. Hamels is a better version, so to speak – so if you pick up his option I would absolutely consider a trade of Q.

            If you are talking about diversifying that offense, a Mallex Smith makes a lot of sense – depending on other trades/signings that involve the OF.

          5. Russell is not a FA. I’d probably go to arbitration with him. He’s bound to lose. I would REALLY struggle agreeing with a decision that renders a W in the arb process given his lack of premium play, and though they are supposed to leave the personal itsh out, it is still hanging over his head like a guillotine.

            Once he is forced to accept the Cubs arb submission — which should be below market value since a win in the arb process is theoretically supposed to get a player to market value — he is probably a lot easier to trade, especially if he goes through some type of DV education and intervention and shows remorse. You still have an uphill battle with his offense, but no one can question his defensive abilities.

          6. Yes, I just meant sign his Arb contract, for little money, and then trade him for BP help. I can’t see him sticking here…too much has happened, DV, injuries, he seems moody. Hoping cubs eventually move on from him b4 ST.

        2. I don’t think we have had a table setter since Fowler left. Merrifield has good numbers vs. RHP and ridiculous numbers vs LHP. If the cost isn’t overwhelming, this type of move could really spark a resurgent offense. KC likely needs more starting pitching, so a Quintana headliner could entice them.

        3. Michael– Great points. Of course, the Cubs would get something back for Quintana, just not as much as they gave up. Also in my book, Dylan Cease still projects as a reliever, so I never regret his inclusion in the deal. That said, since his switch to the White Sox organization, he has lowered his walk rate. Dang, the Sox know how to instruct pitchers and the Cubs don’t.

          1. I’m hoping Cease will start, I have him on the Farm Squad of my AL Dynasty League team. He did have a great year. And though I agree with you on the CgiSox instructors, as well as they do in the minors, only Chris Sale has really met his projections at the major league level – well he exceeded it. I remember when everyone said Sale would be a RP.

  2. I think Merrifield would be available from KC. He is pre-arb, but already 29..speed, power and plus glove in CF. If he hit left handed, he would be perfect. I think Mallex would be a great platoon with Almora. Maybe since Kiermier had a down year, the Rays would move him for young, cheaper talent.

    1. I’d think the Royals would want the kind of prospect depth for Merrifield that the Cubs don’t have but who knows? I just don’t see them trading a pre-arb player for guys that are near arbitration themselves. Smith and Kiermeir could be possibilities I suppose.

      I’d like to see the Cubs get Salazar from the Indians and make him a RP. Guy could be lights out for an inning or two but his health is admittedly a risk. I also like Ottavino but he will probably be very pricey given the money paid to relievers last season.

      I hope Kintzler thinks he is worth more than 1/$5M so the Cubs aren’t stuck with him.

      1. Merrifield only has one exceptional year, but maybe you are right. I would only start the conversation with them if Quintana was what they wanted. Q and a low prospect for Merrifield and a solid prospect. The cost of pitching is high and Q should thrive in KC.

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