The Cubs’ Postseason Dreams Are Over—and So Is Their Would-Be Dynasty

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Chicago’s historic World Series win was supposed to spawn a new power, but the team has delivered a worse result every season since. What went wrong? And can they still build the kind of machine capable of withstanding poor luck?

It could have been a scene from a Disneyfied sports movie. The Cubs had closed to within three games of the Cardinals in the NL Central, and with St. Louis in town for a four-game series at Wrigley last weekend, star first baseman Anthony Rizzo returned to the Cubs lineup just four days after suffering a sprained ankle. Rizzo’s movements were ginger, his fielding hesitant outside the walking boot to which he had been confined, but he strode to the plate in the first game of the series—to the Undertaker’s entrance music, naturally—and rose from the dead to bash a home run.

But life is not a Disney movie; Wrigley Field is not a backlot in Hollywood. The Cubs lost that game, then the next, and then two more over the weekend—all by a single run, and three of the four in the final inning. Closer Craig Kimbrel allowed three home runs across two losses; starter Yu Darvish stayed in for the ninth inning on Sunday to avoid another Kimbrel appearance, only to blow the game himself. After another loss to Pittsburgh on Tuesday, this one aided by five Cubs errors, and yet another loss on Wednesday, Chicago was eliminated from playoff contention. The Cubs still haven’t won a game since Rizzo returned to the lineup, during which time their postseason chances plummeted at an incredible pace.

Thus ends, for good, all chatter about a Cubs dynasty, which rose in the wake of their 2016 triumph: 103 regular-season wins, their first World Series title in a century, a young core ready to dominate the league for years to come. Yet rather than building on that breakthrough, the Cubs have suffered a worse result in each year since. They lost in a shellacking against the Dodgers in the 2017 NLCS, then lost a division tiebreaker to Milwaukee and subsequent wild card game to Colorado last season. In 2019, they missed the playoffs entirely—a disappointment that opens gaping questions about the franchise’s next moves.

The funny thing—or the tragic thing, depending on one’s rooting interest—about the Cubs’ 2019 outcome is that the underlying numbers suggest that this team deserves to play in October. Compared to the Brewers, who surpassed them for the second wild card spot, the Cubs have scored 41 more runs this year. They’ve allowed 54 fewer. Through Tuesday’s games, the Cubs had a Pythagorean record 10 games better than Milwaukee—but the Brewers had overachieved their run differential by eight games, the best mark in the majors, while the Cubs had underachieved by seven, the worst such mark in baseball.

In large part, this discrepancy stems from one of Chicago’s key weaknesses this season: an erratic and unreliable bullpen, despite considerable investment in its construction. The Cubs are 19-27 in one-run games, which ranks 26th in the majors; the four teams worse have all lost at least 100 games overall. And while Cubs relievers have pitched well in low- and medium-leverage situations, they’ve posed a collective disaster in the most important moments.

And even if poor luck is one reason for the Cubs’ playoff miss, drastic changes are still likely to come this offseason. Chicago hopes to be like MLB’s top trio of the Dodgers, Astros, and Yankees—clubs that can seemingly still coast to the playoffs even amid some misfortune. This ambition seems to be one reason behind Boston’s firing of Dave Dombrowski, who won a World Series last season but missed the playoffs this year, and Chicago has the same goal of no lost seasons.

President of baseball operations Theo Epstein won’t depart like Dombrowski, not after bringing the Cubs their first title in 108 years, but Epstein’s handpicked manager will almost certainly be gone after this season. This is the final year of Joe Maddon’s contract, and friction between front office and dugout has grown over the course of many months; by winning percentage, he will leave as the second-most-successful Cubs manager in modern MLB history, behind only player-manager Frank Chance (1905-1912), of Tinker-to-Evers-to-Chance fame.

A broader fix for Chicago must involve a boost to the franchise’s overall player development system, however, not just an adjustment in which man fills out the lineup card each day. Chicago transformed from a last-place afterthought to a juggernaut champion in just two seasons because Epstein engineered a concerted tank, which built the Cubs a talented pipeline to the majors. From 2011 to 2015, the Cubs picked in the top 10 in the MLB draft every year, drawing such players as Javier Báez, Kris Bryant, and Kyle Schwarber into the fold, and supplemented that budding group with trades for Rizzo and Addison Russell, and international signings of Gleyber Torres and Eloy Jiménez. Before the 2015 season, when Chicago won 97 games and reached the NLCS, Baseball America ranked the Cubs’ system no. 1 overall.

Two problems have arisen since then, to the point that now, according to Baseball America’s 2019 midseason report, the Cubs’ farm system ranks 29th. The first is that all those players are now major leaguers, and absent those top-10 picks and future-oriented trades now that they’re a winning club, the Cubs haven’t properly backfilled the pipeline. That’s not an issue in and of itself: The best possible outcome for any minor league push is to eventually produce the kind of core that Báez, Rizzo, and Bryant represent, and the Cubs swapped other prospects like Torres and Jiménez for MLB-ready contributors in Aroldis Chapman and José Quintana, respectively.

But the second problem exacerbates the first: A number of Chicago’s best youngsters haven’t met their MLB expectation. Schwarber hasn’t developed into the indomitable slugger he once seemed; he’s about an average player overall, nothing more. Albert Almora and Ian Happ have both stalled, with the two former top-10 picks combining for negative-0.4 WAR this year. And Russell has never figured out a successful approach at the plate—he’s now a career .240/.312/.391 hitter, which are basically José Iglesias or Jordy Mercer numbers—and has been suspended for violating MLB’s domestic abuse policy.

Chicago’s player development calculus looks much spottier now than it did a half-decade ago. A Driveline Baseball study from earlier this year concluded that the Cubs ranked 26th among the 30 teams in development since 2012—a convenient time span for Chicago, because that was Epstein’s first season with the club. Largely, Driveline found in a follow-up piece, that ranking resulted from two factors: first, a minor league downturn beginning in 2016, and second, a horrid record in pitcher development.

Player development is a terribly tricky realm to quantify, given all the disparate factors that comprise the term, so those numbers certainly aren’t gospel. And to the Cubs’ credit, MLB history shows that merely picking near the top of the draft does not guarantee future stars. By career WAR, Bryant is already the third-best no. 2 pick since 2000—behind Justin Verlander and Alex Gordon—and the players picked ninth overall in the five years before Báez were Billy Rowell (never made the majors), Jarrod Parker, Aaron Crow, Jacob Turner, and Karsten Whitson (never made the majors).

Yet the Driveline results seem to pinpoint the Cubs’ issues rather faithfully. Chicago has struggled to supplement its most elite prospects, leading to a shocking lack of depth. Willson Contreras, signed as the team’s top international free agent in 2009, and David Bote, selected in the 18th round of the 2012 draft, are the Cubs’ only productive position players to come up through the club’s farm system as a non-first-rounder.

The pitching gap is even starker: Of the Cubs’ top 15 pitchers in innings pitched this year, Kyle Hendricks is the only one who made his MLB debut with the club. While the Cubs deserve earlier credit for helping Jake Arrieta transform into a Cy Young winner and for nudging Hendricks from a non-prospect to an ERA champion, they haven’t developed anyone of note since and have dismally failed to churn out capable relievers. Nor does help seem soon on the way: Right now, FanGraphs doesn’t project a single Cubs minor leaguer as even an average pitcher.

For comparison, the Dodgers, Astros, and Yankees each ranked in the top five in Driveline’s study, and each has experienced success with both top-end and lower-tier prospects to sustain their 100-plus-win outfits. In the last few seasons alone, the Dodgers have found castoffs Max Muncy and Chris Taylor, plus a likely MVP in fourth-rounder Cody Bellinger; the Astros have stolen Yordan Álvarez and built an irrepressible pitching machine; the Yankees have salvaged the likes of Gio Urshela and Mike Tauchman, and built a pitching processing line of their own.

The Cubs seem set on tweaking their development processes; they announced earlier this month that Jason McLeod, the amateur scouting and player development leader, will transition to a more MLB-focused role, presaging greater changes still to come. To build a perennial playoff team, this boost should come alongside better free-agent signings, too, as Chicago has whiffed on nearly every signee since 2016. This chart shows every player to whom they’ve committed at least $1 million in free agency since winning the World Series.

The best, by bWAR, is reliever Steve Cishek. Overall, the group has combined for just 7.9 WAR for the Cubs, who probably would have hoped for Darvish alone to be worth that much. But Darvish’s first year and a half with the Cubs were essentially wasted due to injury and underperformance, and he’s not alone with those faults. Of the other highest-profile signings, Morrow hasn’t pitched since July 2018 due to injury, Chatwood never found the strike zone, and Kimbrel has allowed a career-high nine homers in just 20 2/3 innings since starting his season midway through this year.

The Cubs still need to spend money to improve, this winter and beyond; they wouldn’t have won their title without offering lucrative contracts to Jon Lester and Ben Zobrist, for instance, and the Astros have certainly spent on Justin Verlander and Michael Brantley, as well as opened up long-term extensions to José Altuve and Alex Bregman. But can the Cubs make more successful forays into free agency than they have thus far, and will owner Tom Ricketts let them after three years of poor returns? They already tightened the purse strings this past winter—along with seemingly the rest of MLB’s owners—with Ricketts saying that the Cubs “don’t have any more” to spend, and that “as much as I would love to have a great, new, exciting player every single season, it just can’t happen every year.”

That’s a crucial question because Báez, Rizzo, Bryant, and Schwarber will all be free agents after the 2021 season, and Contreras will join them a year later. The Cubs have important choices to make about who to let leave, who to possibly trade, and who to extend—or at least try. Bryant, for instance, reportedly turned down a roughly $200 million offer last year. “I won’t talk about any one player specifically,” Epstein said after the 2018 season, “but I will say that in recent years we’ve very quietly made runs at some of our players to get a long-term extension done. We haven’t been able to. That doesn’t mean we won’t, but it’s proven more difficult than we expected in some cases.”

That notion applies specifically to extending the Cubs’ young position player stars, but it fits just as well with the broader case of extending the Cubs’ competitive cycle. The failure to reach the 2019 playoffs doesn’t mean the Cubs won’t win another title, but it’s proving more difficult than they might have expected.

Comparing Chicago with Houston is instructive. Both teams tanked; both teams rebuilt; both teams emerged on the other side of a last-place flurry with a 100-plus-win champion, in consecutive years. But since their championship, the Astros have won more games each successive year, and once again appear as an imposing title favorite. Houston didn’t just tank; it also invested in free agency and rejiggered its entire organizational approach, for better or worse, to remain at the tip of the league’s analytical spear.

The Cubs still boast a host of extant strengths, from the position player core to a strong defense to a capable if unspectacular group of veteran starting pitchers. Even Darvish, signed through 2023, has perked up in the 2019 second half to admittedly spectacular results: 2.76 ERA, .199 opposing batting average, an astounding 118 strikeouts against just seven walks. They play in a large market with plenty of resources. But the situation is far more muddled than it looked in November 2016, just after Chicago clinched a most fulfilling championship.

By next year, the Cubs might be without that team’s manager and its best player, if rumors about an offseason Bryant trade manifest, as Chicago seeks to streamline its near-term salary commitments and restock the prospect pool. This particular Cubs era will shine forever as a beacon in team history, a triumphant exception to generations of losing and mediocrity—but how quickly an era totters onto unsturdy footing; how swiftly a competitive cycle flows from peak to panic. The Cubs missed the playoffs; that alone is reason enough for dismay. Even worse is the next question, recently unthinkable given the Cubs’ mighty strength: How soon will they return?