The Cubs and the Next Few Offseasons

Cubs fans are rightly excited about the upcoming season. It’s all that most want to think about, and, really, after years of thinking about the future, it absolutely makes sense to enjoy the present.

Front offices don’t have that luxury, though. And if there’s one thing we’ve learned about the Cubs’ brain trust over the past several years, it is this: they always have a long-term plan. Take, for example, the report that they pitched Jason Heyward as the Cubs 2016 centerfielder to Jon Lester in 2014. And then they got both of them.

As excited as we all are for the upcoming season, then, I thought the doldrums of February might be a good time for some educated speculation about how the Cubs might already be planning for 2017, 2018, and beyond. Let’s take a look at some potential holes in the Cubs roster and see if we can figure out how they might be able to fill them. Because even if we can’t know how 2016 will go, history suggests that Theo Epstein and his front office have some pretty good ideas of how the next few offseasons might.

2016-2017 Offseason

Key Losses: Chris Coghlan, David Ross

Likely Areas of Need: Backup Catching, Outfield Depth

The only contracts set to come off the books after this year are mostly small-ish: Coghlan ($4.8 million), Trevor Cahill ($4.25 million), Ross ($2.5 million), Clayton Richard ($2 million), Gerardo Concepcion ($1.2 million), and (finally) Edwin Jackson ($12 million). There will, of course, be ways that the Cubs could further reduce payroll—Jason Hammel’s option could be bought out for $2 million, or perhaps someone could be non-tendered—but for the most part, the roster and payroll will likely look similar heading into 2017. There will be room to add at the margins, and maybe the Cubs would pick up another starting pitcher, but overall there won’t likely be any really significant additions unless the Cubs are about to blow up their payroll to unexpected levels. This creates a pretty stable two-year window for the roster as it stands right now.

This is OK for two reasons.

1) The Cubs roster, as currently constructed, is very very good.

2) The 2017 free agent class is not.

The top position players in the 2017 free agent class are probably Edwin Encarnacion, Jose Bautista, Carlos Gomez, Josh Reddick, Justin Turner, and Yoenis Cespedes (if he opts out). The pitching side isn’t much better: Stephen Strasburg looms head and shoulders above the other names, which include Andrew Cashner and Jaime Garcia (and Aroldis Chapman as a bullpen option). There are some solid players, but outside of mid-rotation starters (who will likely get overpaid in a thin market) and maybe a reliever or two, I can’t really make any particularly compelling cases as to why the Cubs would sign any of them. Having the ability to sit out this free agent class, then, might actually be a luxury—a luxury that the Cubs should be able to afford. This is unlikely to be a coincidence, and it is another example of the well executed long-term roster building that the Epstein front office has pulled off.

2017-2018 Offseason

Key Losses: Jake Arrieta, John Lackey, Jason Hammel, Miguel Montero, Pedro Strop

Likely Areas of Need: Starting Pitching

After the 2017 season, though, things begin to look a little bit different. Barring a series of unlikely extensions, much of the core of the Cubs current rotation—including Lackey, Hammel, and (most importantly) Arrieta—will become free agents. Heading into the 2018 season, then, the Cubs will presumably have to find a way to fill some holes in their starting rotation. By this time, they should have the money to add payroll, but, as with 2017, the 2018 free agent class will leave something to be desired. Arrieta is likely to be the biggest name in that class, well ahead of other pitchers like Tyson Ross, Clay Buchholz, Alex Cobb (assuming health), and Francisco Liriano. Lorenzo Cain, Brandon Belt, Jung Ho Kang, and Todd Frazier look likely to be some of the bigger names on the positional side, which also looks relatively weak.

The thinness of these next few free agent classes underscores why internal development is such a clear focus for the Cubs. Even though the Cubs will have money, they might not have many good external candidates to spend it on. If (when) the Cubs lose Arrieta, Lackey, and Hammel, they will need to have internal options ready to go as contingencies. And, as planned, there do appear to be potentially viable replacements at every position where an opening will appear in the next few years. A combination of Willson Contreras and Kyle Schwarber look likely to be able to succeed Miguel Montero behind the dish. Albert Almora could potentially slide Jason Heyward to a corner outfield spot at some point. And, as Jared Wyllys wrote on Monday, there is a substantial cadre of pitchers—including Pierce Johnson, Duane Underwood, Justin Steele, Oscar de la Cruz, and Dylan Cease—who might be able to fill in a new-look rotation by 2018. The Cubs will likely need to dip a bit into free agency for starting pitching depth, but this organizational depth should give the Cubs payroll space (and trade chips) to work with ahead of what will be an incredibly star-studded free agent class in 2019.

2018-2019 Offseason

Key Losses: Jason Heyward (likely opt-out)

Likely Areas of Need: Right Field, Starting Pitching

Again, right now there isn’t much reason for Cubs fans to look far beyond 2016. But if you do want to ruminate on the future of the Cubs and the league, the 2019 season would be a good place to focus. Here is a list of some top free agents that will be available (or have opt-outs) before 2019:

Positional: Bryce Harper, Manny Machado, Josh Donaldson, Jason Heyward, Andrew McCutcheon, A.J. Pollock, Michael Brantley, Adam Jones.

Pitching: Clayton Kershaw, Jose Fernandez, David Price, Matt Harvey, Dallas Keuchel, Shelby Miller, Garrett Richards, Jose Quintana.


If Cubs can avoid the weaker free agent years and augment their current roster with smart trades and cheap internal prospects, they will be in a fantastic position to be big buyers in this absolutely loaded class. Heyward will very likely opt-out (if he is good over the next few years, he will), but the Cubs will still have excellent (or potentially excellent) players like Kris Bryant, Anthony Rizzo, Addison Russell, Kyle Schwarber, Jorge Soler, Javier Baez, Willson Contreras, and Jon Lester locked up at decent prices. So even if prices do get up into the unprecedented ranges that rumors suggest they will, the Cubs will still have the flexibility to add around this core, most of which will still be on the early side of its prime. Every team will be loading up for this class, but the Cubs will have much to offer.

Who knows—maybe this core and a cool $450 million (or $500 million!) could convince Bryce Harper that playing in New York is kind of passe anyway. Maybe David Price (who has an opt-out of his deal with Boston) might finally be persuaded to reunite with his old manager from Tampa Bay. Indeed, you or I could probably come up with a scenario in which the Cubs sign (or trade for) any of these players over the next few years. And that is kind of the point. With the Cubs’ current set-up, the possibilities are nearly endless—for 2019 and beyond. And that, of course, will be what they planned all along.

Lead photo courtesy Noah K. Murray—USA Today Sports.

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8 comments on “The Cubs and the Next Few Offseasons”


FYI typo in Strasburg’s name. Nice piece. Looks like we can sit out next year in a weak market.

Rian Watt

I could really see Heyward holding out until his 2nd opt out year because 2019 is crazy deep

Nate Greabe

This is a good point and definitely possible, but it might not be worth the risk if he is healthy, playing well, and coming off his age 28 season.

Patrick Nix

The Cubs will not make any significant additions through free agency in the 2017 offseason but they will make a major trade. Jorge Soler will be packaged with a couple top prospects in return for a young cost controlled starting pitcher. Albert Almora will be the starting center fielder in 2017 and Jason Heyward will be back in right field.


As Patrick says, I see a lot of trade possibilities. Contreras and Almora aren’t even in the mix yet and the Cubs already have an excess of quality position players, most very young. They’ll need another quality starter, despite faith in Lackey, Hammel and Hendricks and the collection of “swing” guys I think a legit #2 guy can be pried away from someone in exchange for some nice pieces (Soler and Baez are the first possibilities).

We shall see, as other teams’ fortunes rise or fall, for instance Strasburg could be available as a “rental” later this season if the Nats struggle again.

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