Will Theo Epstein build 2016 ‘super-team’ or try to keep window open longer for Cubs?


Will Theo Epstein build 2016 ‘super-team’ or try to keep window open longer for Cubs?

BOCA RATON, Fla. — Theo Epstein knows the Cubs are walking a tightrope to get back to October, trying to balance their lofty ideals about the future with the reality these next two seasons might be their best chance to win a World Series.  

Putting David Price or Zack Greinke on a team that won 97 games last season and already has Jake Arrieta and Jon Lester at the top of the rotation must be tempting.     

Especially when Arrieta is positioned to become a free agent after the 2017 season, Lester will be 32 next year and soon enough the salary structure for Kris Bryant, Kyle Schwarber and Addison Russell will explode.  

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Plus, the Cubs have sent mixed messages about their next media deal and how soon Epstein’s baseball-operations department will be able to tap into that TV money. Does that mean waiting until 2020 for a new cable network and the huge payroll surge?  

Cubs executives checked out of the Boca Raton Resort and Club on Thursday, the end of the general manager meetings and another step into what should be a dizzying winter.

“It’s hard to argue that the next two years represent a great chance to sort of amass maybe the most talent onto a single roster that we can,” Epstein said before leaving the South Florida hotel. “Because the young guys haven’t started to make a lot of money yet and Arrieta’s locked in and Lester’s pitching at the top of his game.

“One way to look at it is (this) might be the best opportunity to have the single most talented roster that you can. But things get a little more complicated as you move forward.”

The Cubs are worried about becoming a top-heavy team, with two 30-something pitchers making around $50 million combined and taking up too much payroll space.

So maybe signing John Lackey to a shorter-term deal makes sense, since he’s Lester’s buddy, a two-time World Series champion and just went 13-10 with a 2.77 ERA for the St. Louis Cardinals during his age-36 season.

“It’s a balancing act,” Epstein said. “You want to use the dollars that you have available to your advantage, especially when you’re in a position (where) every added win has great impact.

“And then you want to try to avoid a situation where you’re tied into too many big, long contracts that may lead to dead money on the books and inhibit your flexibility in the future.

“We’re out there trying to put the best team we can on the field, given the resources that we have.”

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The Cubs also can’t count on being so lucky or healthy next year after winning 34 one-run games and having four pitchers make 30-plus starts. Realistically, the minor-league pipeline is years away from producing impact pitchers. 

The Cubs don’t sound willing and able to go to the top of the market to sign submarine reliever Darren O’Day, but they kept rebuilding their bullpen on the way to the National League Championship Series.

So the Cubs will hope to strike gold again in the Rule 5 draft – the way they did with Hector Rondon – and find the next Trevor Cahill or Clayton Richard on a minor-league deal (while maintaining interest in re-signing Cahill and bringing back Richard).

There’s also mutual interest between the Cubs and Ben Zobrist, but at this point it’s more about monitoring the situation. The Cubs would probably need to trade one of their young hitters for Joe Maddon’s super-utility guy to become an ideal fit again. And Zobrist’s versatility appeals to teams across the board.

But building a team that’s nimble, deep and multidimensional makes sense, given the financial parameters and a division where the St. Louis Cardinals and Pittsburgh Pirates won 198 games combined this year (and the Cincinnati Reds and Milwaukee Brewers are clearly rebuilding and playing for the future).

“We’re right at that point in the win curve where every win that we can tack onto this roster on paper is potentially really, really meaningful,” Epstein said. “I don’t take that for granted at all.

“Those wins could be really important. They can be the difference between getting in, not getting in. They can be the difference between winning the division or winning the wild card. If things go really wrong, it could be keeping you in contention so you can reshuffle the deck midseason and still make a run at it.”

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Whether or not that involves signing Price, Greinke or Jordan Zimmermann, the Cubs will still be trying to build a perennial contender, especially when everyone knows winning the offseason can mean losing when it actually matters.   

“You can’t count on building a super-team and that will translate to winning the World Series,” Epstein said. “The best way to do it is have really good teams year after year, get in year after year. And eventually you’ll win it.” 

The most underrated storyline of the Cubs offseason

The most underrated storyline of the Cubs offseason

There are plenty of intriguing Cubs storylines to monitor this offseason from their potential pursuit of the big free agents to any other changes that may come to the coaching staff or roster after a disappointing finish to the 2018 campaign.

But there's one question simmering under the radar in Cubs circles when it comes to this winter: How will the team solve the shortstop conundrum?

Just a few years ago, the Cubs had "too many" shortstops. Now, there are several different factors at play here that makes it a convoluted mess.

First: What will the Cubs do with Addison Russell? The embattled shortstop is in the midst of a suspension for domestic violence that will keep him off an MLB diamond for at least the first month of 2019.

Has Russell already played his last game with the Cubs? Will they trade him or send him packing in any other fashion this winter?

Theo Epstein mentioned several times he felt the organization needs to show support to the victim in the matter (Russell's ex-wife, Melisa) but also support for Russell. Does that mean they would keep him a part of the team at least through the early part of 2019?

Either way, Russell's days in Chicago are numbered and his play on the field took another big step back in 2018 as he fought through a hand injury and experienced a major dip in power. With his performance on the field and the off-field issues, it will be hard to justify a contract worth somewhere in the neighborhood of $4 million in his second year of arbitration (prorated, with a month's worth of pay taken out for the suspension).

Even if Russell is on the roster in 2019, Javy Baez is unquestionably the shortstop for at least the first month while Russell is on suspension. 

But what about beyond Baez if the Cubs want to give him a breather or disaster strikes and he's forced to miss time with an injury?

At the moment, there's nothing but question marks on the current Cubs shortstop depth chart throughout the entire organization and they're certainly going to need other options at the most important defensive position (outside of pitcher/catcher). 

There's David Bote, who subbed in for Baez at short once in September when Baez needed a break and Russell was on the disabled list. But while Bote's defense at third base and second base has opened eyes around the Cubs, he has only played 45 games at short across seven minor-league seasons, including 15 games in 2018. There's also the offensive question marks with the rookie, who hit just .176 with a .559 OPS and 40 strikeouts in 108 at-bats after that epic ultimate grand slam on Aug. 12.

The Cubs' other current shortstop options include Mike Freeman (a 31-year-old career minor-leaguer), Ben Zobrist (who will be 38 in 2019 and has played all of 13 innings at shortstop since 2014), Ryan Court (a 30-year-old career minor leaguer) and Chesny Young (a 26-year-old minor-leaguer who has posted a .616 OPS in 201 Triple-A games).

Maybe Joe Maddon would actually deploy Kris Bryant at shortstop in case of emergency like a Baez injury ("necessity is the mother of invention," as Maddon loves to say), but that seems a lot more like a fun talking point than a legit option at this current juncture.

So even if Russell sticks around, there's no way the Cubs can go into the first month of the season with just Baez and Bote as the only shortstop options on a team that with World Series or bust expectations.

The Cubs will need to acquire some shortstop depth this winter in some capacity, whether it's adding to the Triple-A Iowa roster or getting a veteran who can also back up other positions. Right now, the free agent pool of potential shortstops is pretty slim beyond Manny Machado.

Epstein always says he and his front office look to try to mitigate risk and analyze where things could go wrong to sink the Cubs' season and through that lense, shortstop is suddenly right up there behind adding more bullpen help this winter.

Podcast: In light of recent hitting coach turmoil, who’s to blame for Cubs offensive struggles?


Podcast: In light of recent hitting coach turmoil, who’s to blame for Cubs offensive struggles?

On the latest Cubs Talk Podcast, David Kaplan, Kelly Crull, Luke Stuckmeyer and Tony Andracki discuss the comments Chili Davis made after being fired as Cubs hitting coach, ask if the Cubs struggles on offense were Davis' fault or the players and what Anthony Iapoce will be walking into as he tries to gets the team back on track a the plate.


Listen to the entire podcast here, or in the embedded player below: