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How the Cubs Can Become a Dynasty

Stand pat? Sign Clayton Kershaw? Trade for Mike Trout? Technically, it’s all on the table.

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

We don’t talk enough about how inevitable the Cubs’ World Series title felt. This Cubs season was like the movie Titanic — huge, expensive, and wildly anticipated, but in the end it actually won everything and left a song stuck in your head to boot.

A second title, whether in 2017 or in the few years to come, is far from inevitable, but since Theo Epstein hasn’t bailed on the Cubs for an even bigger challenge, one can only assume that’s what he’s after. The Cubs have several paths to a second title (if not more) in the next, say, five years, so let’s see what each one looks like.

1. Do Nothing

The Cubs had the best record in the National League last year, won the NL Central by 17.5 games, and finished with a Pythagorean record of 107–54, the best in baseball by eight games. Bovada has them at 7–2 to repeat, while no other team gets better than 10–1 odds.

This offseason, the Cubs stand to lose Dexter Fowler, Travis Wood, Jason Hammel, and Aroldis Chapman to free agency, which are not trivial losses: Chapman is at worst one of the five best relievers in the game, Fowler is an All-Star center fielder who just posted a .393 OBP, Wood is a good rubber-armed middle reliever, and Hammel threw 166.2 innings with a 105 ERA+ last year.

On the other hand, Hammel didn’t dress for a single playoff game, you can find middle relievers, and even if the Cubs don’t bring Chapman back, they could go out and sign Kenley Jansen or Mark Melancon — or just roll Hector Rondon back out as the closer — and not miss a whole lot. If Fowler walks, it will be a loss, but even if all the Cubs do is start Albert Almora Jr. in center, the downgrade isn’t going to wipe out the Cubs’ enormous head start on their competition in 2017.

The Cubs’ front office brain trust could go on vacation until February, leaving only an intern to make sure arbitration paperwork gets filed on time, and the Cubs would still be overwhelming favorites to win the World Series in 2017. In fact, attrition isn’t going to kill the Cubs until 2022. Here are the key players from the 2016 title team, listed by how long the Cubs can control their rights:

  • Through 2016: Fowler, Wood, Hammel, Chapman
  • Through 2017: Jake Arrieta, John Lackey, Miguel Montero
  • Through 2018: Rondon
  • Through 2019: Ben Zobrist
  • Through 2020: Kyle Hendricks
  • Through 2021: Kris Bryant, Anthony Rizzo, Addison Russell, Javier Báez, Jon Lester, Kyle Schwarber

This leaves out some minor contributors, but if the fate of the 2020 World Series hinges on the Cubs letting Justin Grimm walk, I hope you’ll forgive me for not foreseeing it this far out. They’ll have to start turning over the rotation as soon as next year, but apart from that, the Cubs won’t lose anyone truly irreplaceable for another five years.

2. Let the Kids Take Over

The Cubs are where they are because of an incredible run of acquiring and developing young talent, but after years of having one of the best farm systems in baseball, the pipeline is starting to dry up a little. Because the Cubs’ title is viewed as a victory for a certain type of front office — the kind that builds on young players who have undermarket contracts — it’s tempting to think that the depletion of the Cubs’ farm system is a bad thing. Please let me disabuse you of that notion.

The Cubs’ minor league system is depleted for two reasons: First, most of the good prospects either got promoted and are significantly contributing to the big league club or were traded for established veterans who are contributing to the big league club. Second, the Cubs aren’t drafting in the top 10 anymore because they’re winning and signing big-name free agents. Surely Chicago would rather have Kris Bryant, at age 24, winning the MVP and the World Series than hitting like crazy in Triple-A as the no. 1 prospect in baseball.

So who’s left?

MLB Pipeline puts four Cubs in its top-100 rankings: Ian Happ, Eloy Jimenez, Dylan Cease, and Jeimer Candelario.

Candelario, a switch-hitting third baseman who turned 23 last week, had a cup of coffee with the Cubs in 2016 after hitting .333/.417/.542 in 309 plate appearances at Triple-A. Unfortunately for Candelario, the Cubs won’t need a third baseman until 2022 at the earliest. The 20-year-old Cease fell to the sixth round in the 2014 draft after Tommy John surgery, and while the hard-throwing righthander gets folks all googly-eyed when he’s on the mound, he ended last season in low-A and has only 68.2 career minor league innings under his belt. It’d take a minor miracle for Cease to slide into Lackey’s spot in the rotation at the start of 2018.

That leaves Jimenez and Happ. Jimenez, a big goddamn corner outfielder (listed at 6-foot-4, 205 pounds) who just turned 20, broke out at the Futures Game, where he sacrificed his sunglasses to make an acrobatic catch in the right-field corner, then took hard-throwing Rays prospect Ryne Stanek out off the third level of the Western Metal Supply Co. building in San Diego. But while prospect evaluators are singing “Hail Eloy, Full of Tools,” he probably won’t be ready for the big leagues for another two years, perhaps to replace Zobrist in left field as he ages out of the lineup.

But the more direct replacement for Zobrist, as a multipositional switch hitter, is Happ. I’ve been a huge Happ fan since his college days because he just does everything well. He’s played second base and all three outfield positions in the minors, and he’s a true switch hitter with a good feel for the zone and double-digit home run power. And for what it’s worth, Happ was the third straight polished college hitter Epstein and friends spent a top-10 pick on — the two others were Schwarber and Bryant. Happ isn’t quite that talented, but he could be up as soon as the middle of 2017, which makes him able to contribute more quickly than Cease or Jimenez, and his upside is higher than Candelario’s.

Of course, the Cubs’ record of pulling stars out of my-garbage-for-your-trash trades (Hendricks, Rizzo, Arrieta) means that there could be a sleeper in this system. Like, it wouldn’t shock me if Jake Stinnett suddenly showed up in big league camp with Brandon Webb’s forkball, because that’s just the run the Cubs are on right now. But barring a surprise like that, there isn’t another Bryant coming down the pipe in the next year or two, and the Cubs’ two biggest immediate needs — starting pitcher and center field — don’t have immediate solutions.

3. Make a Big Trade

Despite Bryant, Zobrist, Báez, and Willson Contreras being able to play multiple positions (as could Russell, but since he’s an elite defensive shortstop, why would you want him to?), the Cubs’ position-player talent is imperfectly distributed on a positional basis. For instance, because the Cubs have no DH, a lineup full of sluggers, and a superstar first baseman, there might not be a team in baseball that needs Schwarber less than Chicago.

What this extremely nitpicky criticism of the Cubs’ player development system means is that while the team should by no means be desperate to trade Schwarber or Candelario or Jorge Soler for whatever they can get, they should absolutely be open to using their surfeit of corner guys to land a pitcher or center fielder of equal talent.

But of course they’ll deal from some of this surplus to replace Fowler this year or Arrieta next year — that’s almost a given. Whether they dump out the farm system for Chris Sale or go for a mid-rotation guy, and which prospects go the other way, remains to be seen, but let’s be honest, that’s not the fun question. The fun question is the one you’re all thinking anyway: What would it take for the Cubs to trade for Mike Trout?

Trout has been the best position player in baseball for five years. In any individual season, you can cherry-pick stats and narratives to pull Miguel Cabrera, Josh Donaldson, Bryce Harper, or Mookie Betts up into arguing distance, but any AL MVP case since 2012 has either been made for Trout or in direct opposition to Trout. He’s the gold standard, and at 25, he will be for a while. Even at upward of $34 million per year from 2018 to 2020, he’ll be a bargain.

To convince the Angels to part with him, you’ve got to give GM Billy Eppler a package of players that will make up for Trout’s absence (which in the real world, unlike Out of the Park Baseball, is more complicated than putting together an offer of four quarters for a dollar bill). You’ve got to sell it as being on Eppler’s timeline for contention (which, given the Angels’ organizational paucity of non-Trout talent at any level, is flexible), and better from a cost perspective.

And you’ve got to do it convincingly enough that Eppler is comfortable having “Billy Eppler, Who Traded Mike Trout” go on his tombstone, because that’s going to be his professional legacy. It’d be the most discussed baseball transaction since … I don’t even know … Alex Rodriguez signing with the Rangers? Barry Bonds signing with the Giants? The sale of Babe Ruth? Eppler wouldn’t make this deal unless he was certain it would be a win.

He’d also have to be certain enough to sell Angels owner Arte Moreno on it. There are two kinds of deep-pocketed sports owners: hands-off types who hire smart people and disappear except to sign checks and collect trophies, and self-sabotaging egomaniac loudmouths like Mark Cuban and Jerry Jones. Moreno falls in the latter camp, and would probably require even more convincing than Eppler.

So take whatever mélange of bench bats you wanted to offer and chuck it out the window. If you think this is the deal where you can bury Jason Heyward’s contract or cling to Báez because you like watching him catch throws to second base, you’ve got Trout confused with Yasiel Puig and Eppler confused with the guy you kicked out of your fantasy league after he didn’t look at his roster once all year.

Chicago, this one’s going to hurt.

How about Schwarber, Happ, Jimenez, Cease, and Candelario and add in Báez? The Cubs can move Zobrist to second base and play Trout in center and find a left fielder in the couch cushions. But why would the Angels do that? Schwarber, for all the hype about his World Series return, is essentially a DH, and the Angels still have five more years of Albert Pujols, who’s even slower than Schwarber. And if Trout’s a 10-win player right now, nobody going the other way has anything more than a trivial chance of being more than a five-win player year-on-year. The Angels’ farm system is in such dire need of depth that it could actually use some filler, but you don’t trade the best player of the past 10 years to get filler.

No, if the Angels were going to trade Trout, they’d want at least one crack at developing an MVP-caliber player out of the trade return, and the Cubs don’t have one to offer among their prospects.

They do, however, have one in their lineup: What if the Cubs were willing to part with Bryant?

Comparing the two directly, Bryant — who again just won and deserved the NL MVP award — is still a big downgrade from Trout. Bryant’s MVP 2016 was a 7.7-bWAR season, which would’ve been (by a fraction of a win) Trout’s worst full season in the big leagues. Trout’s career OPS+ is 170, Bryant’s 142, and while Bryant can play third base and both outfield corners, Trout can play center. And while Trout has three years of service time on Bryant, he’s only six months older, and thanks to his extension, he’ll reach free agency only a year earlier.

If Bryant doesn’t sign an extension — and as a Scott Boras client with an active grievance for service time manipulation, I wouldn’t bet on it — he’ll probably be cheaper than Trout. He also looks better on a billboard, but other than that, there’s still a gap to be made up.

Would Schwarber and Jimenez fill that gap? I’d certainly think about it if I were Eppler. The Cubs could either move Zobrist to second and Báez to third or just plug Candelario in, while Trout plays center. But that’s the kind of deal it’d take. If you’re trying to trade for the best player in baseball, everything is on the table.

4. Sign More Big Free Agents

If I ran the Cubs, I’d try to trade my way to Pareto efficiency, but unless a bargain presented itself on the trade market, I’d look to free agency for my next star. Chicago’s catcher-infield combination of Contreras, Rizzo, Báez, Russell, and Bryant includes two MVP-caliber players and three others who are at least average-to-above-average, and the 27-year-old Rizzo is by far the oldest among them. More than that, not a single one of those five players is going to make within $15 million of what he’s worth next year. Bryant and Russell don’t even hit arbitration until after next season, Schwarber and Contreras the year after. Rizzo, meanwhile, is on Year 5 of a seven-year contract worth $41 million guaranteed total, with two team options after that.

Now let’s consider the Cubs’ financial situation: Their payroll was about $171.6 million, which means they could’ve almost fit another Heyward under the $189 million MLB luxury tax threshold. They’re the most popular team in the third-biggest city in the United States, with some of the highest ticket prices in the game, and after sending Chicago (and the Western world at large) into a rapturous frenzy, they’re going make enough selling jerseys and hats and commemorative DVDs to be able to buy New Mexico and turn it into a winter training facility. Even as the infield and Hendricks are due for incremental raises from 2018 to 2020, Heyward’s and Zobrist’s contracts are contoured so that they get big raises this year. Their salaries drop by a combined $12 million from 2018 to 2019, which will offset Rizzo’s raise and some of the arbitration awards to the other players. Plus, Heyward could opt out after 2018 or 2019, which is still possible even if it looks unlikely at the moment.

In other words, given how little the backbone of the team is being paid, if the Cubs don’t spend to the tax in each of the next five years, fans should picket Wrigley Field.

For that reason, unless the Cubs could get Sale at a bargain rate, they might be better served replacing Lackey and Arrieta after next year in free agency. Though this year’s free-agent pitching class is barren, Yu Darvish and Alex Cobb will be free agents after 2017, and so will Masahiro Tanaka and Johnny Cueto if they opt out of their contracts.

Or you can look at it this way: Depending on what Arrieta makes in arbitration this year, the Cubs will probably take about $45 million off their books when he, Lackey, and Montero hit free agency after this season. You know what you could do for $45 million a year? Re-sign Lackey and Arrieta.

Then there’s the monster 2018–19 free-agent class. Some of these players will likely sign extensions or decline to exercise their opt-outs, but right now it looks like Bryce Harper, Clayton Kershaw, Michael Brantley, Josh Donaldson, Matt Harvey, Dallas Keuchel, A.J. Pollock, and David Price, among countless others, could all hit the market at the same time. Certainly the Cubs could scare up some money to add the likes of Harper or Donaldson to a team that’s already poised to make a run at dynastic status.

Because, remember, the Cubs are going to be World Series favorites again next year even if they do nothing.