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.

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