The legacy of the 2016 Cubs will forever be that they broke the longest title drought in American professional sports. And for good reason. But the vivid clarity of that legacy blocks out how incredible that team was. Chicago won 103 games and had the run differential of a 107-win team. Kris Bryant and Anthony Rizzo finished first and fourth in MVP voting, respectively, while Jon Lester and Kyle Hendricks finished second and third in Cy Young voting. The pitching staff allowed 56 fewer runs than any other National League team and posted a 133 ERA+, tied for the second-best mark by an NL team since 1954. Meanwhile, the Cubs offense tied for the NL lead in OPS+ and finished second in runs scored to the Rockies. They won their division—which the year before had produced the three best teams in baseball by record—by 17 1/2 games.
Combining regular-season and playoff accomplishments, the 2016 Cubs are probably the best single-season National League team since the 1994-95 strike. And they weren’t a one-hit wonder; Chicago made the NLCS three years straight from 2015 to 2017. The lineup that started Game 7 of the 2016 World Series featured seven position players in their age-26 season or younger, and every starting position player other than center fielder Dexter Fowler was under contract through at least 2019. Reinforcements were on their way, too: The club had four top-100 prospects—Ian Happ, Dylan Cease, Eloy Jiménez, and Jeimer Candelario—still in the pipeline.
The moment Bryant threw out Michael Martínez to close out the 2016 World Series, a second title was treated as a foregone conclusion. A few weeks after, I wrote a column exploring the many team-building options Chicago could pursue in service of a second, or even third, title. They had the prospects, big league talent, and financial wherewithal to make a run at Clayton Kershaw or Mike Trout, or they could just let it ride and probably hoist the Commissioner’s Trophy once more with the same core.
Suffice it to say, things have taken a hard left turn off that course.
After ending their championship drought, the Cubs have started another ignominious streak—this time, in the region of free agent spending. The Cubs are the richest, most popular baseball team not only in the NL Central, but in the entire area between the Appalachians and the Rockies. But since winning the World Series, they’ve gone from one of the most active free agent buyers in the league to a near nonparticipant. After a quiet 2018-19 offseason, the Cubs have signed zero free agents to guaranteed major league contracts so far this winter. The sum total of the Cubs’ activity so far is two minor league deals, plus a pair of one-year split contracts for relievers Ryan Tepera and Dan Winkler, who are guaranteed a combined $500,000 this season. Neither would make even a million dollars next year if they play at the big league level.
That’s a problem. In the 2018-19 offseason, the vast majority of MLB teams independently (and inexplicably) didn’t pursue the top free agents in the class. This hot stove season, however, has proceeded more or less normally, which means that 25 of the top 28 names on my November free agent ranking have already signed. Two of the three exceptions are Josh Donaldson—who’d be essentially useless on a team that already has Kris Bryant—and Nick Castellanos, who was the Cubs’ best hitter down the stretch last year. The Cubs have kept their powder dry for no particular purpose; few of the remaining available free agents would be more helpful to the 2020 Cubs than a bag of actual dry powder.
This course of inaction fits with an ongoing trend. The backbone of the championship Cubs team was built internally. Along with the Astros, the Cubs benefited from executing a hard tank in the years before it became a common strategy and the advantage of going against the grain disappeared. In contrast to Houston, however, whose draft record under general manager Jeff Luhnow is mixed, the Cubs went on an all-time scouting and development heater. From 2011 to 2015, the Cubs drafted in the top 10 every year, and spent those picks on—in order—Javy Báez, Albert Almora, Bryant, Kyle Schwarber, and Ian Happ. All five turned into solid big league regulars, and Báez and Bryant are now among the very best position players in the National League. The Cubs also traded for Anthony Rizzo, Jake Arrieta, and Hendricks during that time, all young players who initially didn’t look like anything special but later grew into stars.
That’s a great core, but even that wasn’t enough to win a title. Before the 2015 season, the Cubs signed Lester to a six-year, $155 million contract, and the offseason before their title run, they inked four free agents—Jason Heyward, Ben Zobrist, John Lackey, and Fowler—to contracts worth at least $13 million a year. While Heyward has been a disappointment, Fowler led the 2016 Cubs in OBP, Lackey made 29 starts with a 125 ERA+ in 2016, and Zobrist hit .272/.386/.446 and was named MVP of the World Series.
In the four offseasons since, though, the Cubs have signed just two free agents—Yu Darvish and Craig Kimbrel—to similarly lucrative contracts. For a team that’s supposedly one of baseball’s biggest financial players, Chicago’s free agency practices since winning the World Series have been conspicuous, and seemingly tantamount to a capital strike.
Now, the Cubs aren’t a typical big-market team. Having Bryant, Báez, and Rizzo in the lineup, plus Hendricks and Lester in the rotation, they haven’t really needed a middle-of-the-order slugger or a no. 1 starter like some of their competitors. And when a need did arise, they tended to fill it through midseason trades, as evidenced by the deals that netted them José Quintana and Cole Hamels in 2017 and 2018, respectively, as well as the 2019 deadline deal that brought Castellanos over from Detroit.
And the Ricketts family, which owns the team, does have a lot of cash tied up elsewhere. Pete Ricketts, the current governor of Nebraska, spent $125,510 of his own money in his 2018 reelection campaign, plus he got $60,691 more in donations from the team. This is on top of the $200,000 that Ricketts spent on a petition to reinstate the death penalty in Nebraska. These are petty sums when a top MLB free agent can go for $30 million a year, but had ownership diverted money from its self-funded political campaigns, the Ricketts family could have put that money in the bank and used it to almost double their free agent expenditures this offseason.
Then there are the budget overruns on the half-billion-dollar, non-ADA-compliant renovation of Wrigley Field to consider, which is a bigger line-item expenditure but represents a capital improvement that would theoretically raise the value of the franchise. The long-term benefits for the Ricketts family in that respect are obvious, but luxury boxes won’t do as much to help the 2020 Cubs as, say, signing Hyun-Jin Ryu would have.
Even more curious than the Cubs’ decision to sit free agency out, however, is how inexplicably terrible they’ve been at picking their free agents since 2016.
On December 16, 2017, the Cubs signed relief pitcher Steve Cishek to a two-year, $13 million contract. During the next two seasons the right-hander made 150 relief appearances and posted a combined ERA+ of 169, which is a pretty solid bullpen performance for $6.5 million a year. Outside of Cishek, though, the rest of the Cubs signings have been either bewildering or ineffective.
In 2017, the Cubs replaced closer Aroldis Chapman with 42-year-old Koji Uehara, who went on to have his worst season since his rookie campaign (a 111 ERA+ in 43 innings). He returned to Japan the next year. The same season, they replaced Fowler with Jon Jay, who hit .296/.374/.375. Both Jay and Uehara were on relatively inexpensive one-year deals, and were fine, if not spectacular. But that’s still a cut above your garden-variety Cubs free agent signing.
Also in 2017, Chicago signed Brett Anderson for one year and $3.5 million. He made six starts with an ERA north of 8.00 and was released midseason. That offseason, the Cubs gave Drew Smyly a two-year, $10 million deal. He didn’t throw a single pitch for the club and was traded to the Texas Rangers that offseason. In December 2018, the Cubs signed Kendall Graveman to a one-year deal for $575,000, probably figuring that they had to hit big on an injury-prone starting pitcher eventually. Graveman did not throw a pitch for Chicago, or indeed any major league team, last year. And considering that he’s since signed with the Seattle Mariners, he may not pitch for a major league team in 2020 either.
There are, however, worse things than not pitching in the majors. The Cubs know this, having signed Tyler Chatwood to a three-year, $38 million contract before the 2018 season, to which Chatwood responded by showing levels of wildness hitherto unseen outside the imagination of Maurice Sendak. That same offseason, the Cubs made their biggest free agent venture since Lester by lavishing a six-year, $126 million deal on Darvish, who’d been one of the top pitchers in baseball throughout the 2010s. Darvish made just eight starts in 2018, in which he had nearly as much trouble finding the plate as Chatwood, before bouncing back to make 31 starts with a 112 ERA+ in 2019—solid, but not the ace-level performance one would expect given Darvish’s reputation and price tag.
The Cubs limited last offseason’s free agent spending to a $5 million deal for infielder Daniel Descalso (.173/.271/.250), a $3 million contract for reliever Brad Brach (who posted a 6.13 ERA in 42 appearances before his August release), and a few six-figure tryout deals for bullpen arms. Then, in June, with the NL Central race too close for comfort, the Cubs threw $43 million over three years at Kimbrel, the best relief pitcher of his generation.
Kimbrel, who’d sat out the first two months of the season as he waited to be signed, took nearly three weeks to ramp back up to game fitness. He delivered a scoreless one-inning save in his debut on June 27, but in his other 22 appearances with the Cubs, Kimbrel posted an 0-4 record with a 6.86 ERA, blew three saves, and allowed an opponent slugging percentage of .662. Maybe the Cubs’ front office has decided they’re so bad at free agency that it’s just not worth trying anymore. That would certainly be a relatable impulse.
The problem is, if the Cubs aren’t going to strengthen the big league roster through free agency, they have to find other ways of doing so—and that isn’t happening either. The prospect pipeline that shaped the title-winning team has dried up, which not only deprives the Cubs of internal help, but also means that if they want to make a big-name trade, they’ll have to cannibalize the active roster. Many of the Cubs’ most helpful trade acquisitions—Hamels, Castellanos, Daniel Murphy, Wade Davis, Brandon Kintzler—have since departed via free agency themselves.
Along with failing to bring in reinforcements, the Cubs have also failed to use their money to retain the club’s existing stars. Rizzo, Bryant, Báez, and Schwarber will all be free agents after the 2021 season. So will Quintana after the 2020 season. The only homegrown players the Cubs have managed to sign to long-term extensions since winning the title are Hendricks and (for some reason) utility infielder David Bote.
If the Cubs aren’t re-signing their existing stars, aren’t signing any free agents, and aren’t developing the next generation’s equivalent of Bryant, Rizzo, and Báez, then it’s not clear how, or even if, they intend to win another title. Maybe free agency will be easier to navigate before this title drought reaches 108 seasons.