There was a time, in both of the offseasons following 2015 and ‘16, when some awfully bold proclamations were made. Many seemed to be certain that the next great dynasty in Major League Baseball would be led by this group of Cubs, fueled by more hope in Chicago than at any point of the club’s near 150-year existence. 

2015 and 2016: A North Side Renaissance

The Cubs launched themselves into contention in 2015, with a 97 win season that took many by surprise. They earned a Wild-Card berth, and shutout the Pittsburgh Pirates 4-0 in a winner-take-all matchup.

The Cubs moved on to an NLDS date with the St. Louis Cardinals, the first ever playoff meeting between the longtime rivals. Chicago ousted St. Louis in four games, moving on to the League Championship Series. They were swept in the NLCS by the New York Mets in convincing fashion, but nevertheless, optimism for the future was contagious among the organization and fanbase.

Excitement for the upcoming 2016 season boiled over when the Cubs made a major free agency splash, landing veteran infielder Ben Zobrist, starting pitcher John Lackey, and rising star Jason Heyward for a combined $276 million.

At this point, the Chicago Cubs were no longer a lovable underdog; they were a World Series favorite. Many teams would have allowed the pressure of a World-Series-or-bust mentality to weigh them down. The Cubs, however, did not miss a beat. Led by Joe Maddon’s “never let the pressure exceed the pleasure” mantra, the North Siders plowed their way to a 103-58 regular season, a division title, and homefield advantage throughout the NL playoffs. They would win the World Series in seven games, coming back from a 3-1 series deficit, and finally ended the 108 year title drought that had hung like a dark cloud over the franchise for an eternity.

Looking Back: How the Cubs Built a Winner

The organizational strategy that led the Cubs to a World Series Championship was focused on stockpiling star position players through the draft and a lucrative trade or two, while building a pitching staff by utilizing free agency and the trade market. In the years before the team was competitive, they set out to acquire pitching that they could eventually flip in deals for prospects. This plan was set in motion with the trades of Ryan Dempster to the Texas Rangers for Kyle Hendricks in 2012, Scott Feldman to the Orioles for Jake Arrieta and Pedro Strop in 2013, and Jeff Samardzija and Jason Hammel to the Oakland Athletics for Addison Russell in 2014. 

Hendricks, Arrieta, and Russell would play major roles in the Cubs’ 2016 championship. 

The Cubs also used the free agent market, along with the power of ownership’s deep pockets, to secure the finishing touches of a winning ballclub. Chicago landed ace lefthander Jon Lester on a six-year, $155 million deal in the winter of 2014. They also added the aforementioned Ben Zobrist (four years, $60 million), John Lackey (two years, $32 million), and Jason Heyward (eight years, $184 million). 

The North Siders looked back to the trade market in search of one final piece to fortify their bullpen before the trade deadline in 2016. The Cubs shipped future superstar infielder Gleyber Torres to the New York Yankees for fireballing closer Aroldis Chapman. The left handed reliever would prove absolutely key to the Cubs’ 2016 title run, as Chicago’s organizational position player depth allowed them to make a high impact move that directly lead to a championship.

The Cubs had constructed a World Series-caliber roster from the ground up. Featuring star position players in Kris Bryant, Anthony Rizzo, Willson Contreras, Javier Baez, and Ben Zobrist, along with proven, all-star quality pitching in Jon Lester, Jake Arrieta, and Kyle Hendricks, the Cubs were stacked from top to bottom. After the infamous curse was broken in 2016, it appeared the Cubs were set to make runs at the Fall Classic for years to come. However, through their own doing, along with some misfortune, it was simply not meant to be.

What Went Wrong?

Following 2016, President of Baseball Operations Theo Epstein and General Manager Jed Hoyer continued to execute the plan that had so effectively led them to greatness. After the title run of the previous season, the Cubs struggled for the first half of 2017, perhaps due to the often overblown concept of a “World Series Hangover.” Nonetheless, the Cubs sat at 43-45 at the ‘17 All-Star break, 5.5 games behind the first-place Milwaukee Brewers. In the familiar blueprint of the Aroldis Chapman trade, the Cubs dealt prospects Eloy Jiménez and Dylan Cease to the White Sox in exchange for veteran left-handed starting pitcher José Quintana. At the time, Jiménez and Cease were the top two overall prospects in the Cubs’ system, with Jiménez listed as the eighth-best prospect in all of baseball, according to MLB’s official rankings.

The Cubs shipped a massive haul of talent to their crosstown rivals, and many were skeptical of the deal from the moment it was announced. However, the Cubs viewed the talented Quintana as a valuable rotation piece for the 2017 season and for the three future years of team control remaining on his contract. 

As one of the more underrated arms in all of baseball, Quintana had established himself as one of the most reliable starting pitchers in the league. From his first full Major-League season in 2013 through the 2016 campaign, Quintana posted a stellar 3.35 ERA (3.34 FIP), and was honored as an American League All-Star in ‘16. During the same period from ‘13 to ‘16, the lefty started at least 32 games and reached 200.0 innings or more in each of the four seasons, a stretch in which he was 7th in fWAR among starting pitchers.

The Cubs hoped these trends would hold steady for their prized acquisition, yet Quintana has fallen off a bit since his move uptown. While he has certainly been solid during his time with the Cubs (4.23 ERA, 3.95 FIP across two-and-a-half seasons), he has only shown brief flashes of his top-of-the-line potential since the mid-2017 trade. 

Moreover, while the 2017 season was certainly not a failure – the Cubs won the NL central division and made it to the NLCS for the third consecutive year – much of the mindset around that team, and its underlying problems which were not addressed, set up the disaster of the two years to follow.

As the Cubs raided the cupboard in terms of the prospect currency within their organization, they became the accomplices of their own demise. A weakened farm system has handcuffed the Cubs in the years since 2017, as it has both limited their flexibility to make other trades, as well as darkened the outlook on the future of the Major-League roster. 

Further, when addressing the free agent deals that have turned into albatrosses for the Cubs, one fact must remain clear: an ideal ownership group is always one that allows the franchise to spend large amounts of money in free agency, with the goal of winning baseball games in mind. Teams that spend are almost always going to have more success than those who do not.

However, financial resources, even for a big-market team like the Chicago Cubs, are still finite. The large contracts of Jon Lester and Ben Zobrist have undoubtedly been worth every penny, but those of Jason Heyward ($184 million), Tyler Chatwood ($38 million), and Brandon Morrow ($21 million) have weighed the front office down. The jury is still out on whether Yu Darvish ($126 million) or Craig Kimbrel ($45 million) will live up to their massive contracts.

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In recent offseasons, team chairman Tom Ricketts has stated rather bluntly that the team cannot continue to spend recklessly. The fanbase was outraged when Ricketts cried poor, and it is reasonable to feel that the word choice of these comments was in poor taste. Obviously, the Ricketts’ have plenty of money, but they are not obligated to spend more than they wish on their baseball team. The Cubs had the second highest Opening Day payroll in Major-League Baseball in 2019 ($208.2 million), and that figure increased with the midseason addition of closer Craig Kimbrel.

The bottom line is that $208.2 million should always be enough for a front office to build a strong roster. In 2019, the Cubs were a massive disappointment, despite the huge payroll, and finished with a record of 84-78. Much of the blame for a failed season certainly lies with the players and manager Joe Maddon (who was let go after the 2019 season, and replaced by David Ross), but the front office, especially Theo Epstein and Jed Hoyer, should also be heavily scrutinized. 

The additions of Heyward, Chatwood, Morrow, and Kimbrel appeared to be forward-thinking moves at first, but the players simply have not performed up to their lofty expectations. 

Heyward was a 5.6 fWAR player for the St. Louis Cardinals in 2015, yet his combined fWAR total in four seasons as a Cub is just 6.0.

Chatwood was expected to be a valuable rotation piece and potential breakout candidate when he arrived in Chicago, with top-of-the-line stuff and skewed home/road splits during his time as a Colorado Rockie (which is to be expected). His time with the Cubs has been a disaster. Chatwood led the Majors in walks allowed in 2018, issuing 95 free passes in just 103.2 innings pitched, leading to a 5.30 ERA and an even worse 5.60 FIP for the right-hander. He did bounce-back somewhat in 2019, proving to be a useful (yet expensive) bullpen piece and occasional spot starter, with a 3.76 ERA (4.28 FIP) in 76.2 innings pitched. 

Morrow pitched in just thirty-five total games for the Cubs, missing the entire 2019 season. If his contract is viewed with a price-per-appearance perspective, Morrow cost the Cubs $600,000 for each of the games in which he pitched. The righty will be an unrestricted free agent entering the 2019-20 offseason, and it has been rumored that he could return to the Cubs on a Minor-League deal.

Kimbrel struggled mightily in his first year as a Cub in ‘19, posting a 6.53 ERA (8.00 FIP), blowing three save opportunities and recording four losses. He’ll hope to significantly rebound next season. The Cubs certainly hope that he will drastically improve, as the team will owe their appointed closer $32 million over the course of the next two seasons, with a $16 million vesting option for 2022.

2018 and 2019: A Fundamental Collapse

The result of a series of ill-fated decisions by the front office led to two agonizing seasons for the Chicago Cubs in 2018 and ‘19. 

The ‘18 campaign was a strange case, as the Cubs won 95 regular-season games but failed to reach the NLDS. The first half of the season was a strong one, as the Cubs rolled into the All-Star break following a three-game sweep of the San Diego Padres, with a record of 55-38. The Milwaukee Brewers lost six in a row prior to the break, allowing the Cubs to reach a season-high 2.5 game lead in the division.

The second half of the season was plagued by offensive struggles. In the first half, the Cubs averaged 5.12 runs per game, with a team OPS of .771. In seventy games after the All-Star break, those numbers plummeted to 4.07 and .705, respectively, highlighted by a .663 team OPS over the final twenty-nine regular season contests. 

On paper, it is hard to define the end of the 2018 season as a collapse for the Cubs. They posted a 16-12 record in September, which is obviously not a case of a team that “choked”. The Cubs had a 2.5 game lead heading into the final week of the regular season, with their final seven games at Wrigley Field. The Cubs then struggled against a lowly Pirates team, splitting a four-game series, and were not able to sweep a three-game set against an eliminated (for all intents-and-purposes) Cardinals club. Meanwhile, the Brewers caught fire, winning seven straight to force a tie-breaking Game 163.

The well-publicized offensive breakdown of the ‘18 Cubs was encapsulated in a 3-1 loss in Game 163 to the Brewers, and even more so in the season-ending, thirteen-inning, 2-1 Wild Card loss against the Colorado Rockies. The Cubs scored a grand total of 2 runs over the course of 22 combined innings and two must win games, both at Wrigley Field. Their season slipped away, resulting in a team which finished with the second highest win total in the National League appearing in only one playoff game.

Reality Check: The 2018-19 Offseason

Following a scathing end-of-season press conference from Theo Epstein in which he described the offense as “broken,” the 2018-19 offseason was extremely bizarre for the Chicago Cubs. It was a strange free agency period across all of baseball in general, as the market was dreadfully slow. However, the lack of activity for the Cubs, in free agency or the trade market, was particularly alarming.

The 2018 team was unquestionably talented, yet far from perfect. The roster had obvious flaws, and was missing key pieces that could have prevented some of the difficulties the team faced in September of ‘18.

Therefore, following Theo Epstein’s comprehensive comments regarding the state of the team, it was to be expected that some significant improvements were in store for the Major League roster. If nothing else, many assumed that major changes would be made in order to shake things up and rejuvenate the proven core of stars that the Cubs were supposed to be building around.

In spite of a clear need for change, the Cubs did next to nothing during this critical offseason. The front office could absolutely have addressed the critical need for bullpen and position player depth (especially in the outfield), yet they effectively attempted to patch up a sinking ship with Duct Tape. Their only notable additions were the signings of veteran infielder Daniel Descalso (two years, $5 million) and aging reliever Brad Brach (one year, $1.65 million, with additional incentives). 

The Cubs did retain left-handed starting pitcher Cole Hamels by picking up his $20 million team option for the ‘19 season, which was a solid move that helped bolster their rotation. 

Slow, Painful, and Inevitable: The 2019 Season

The definition of insanity is doing the same thing over and over again, while expecting different results. This is how the Cubs approached the ‘19 season: they rolled out the same team that had fallen on their faces at the end of ‘18, and were content with allowing the same group of players to essentially “try again.” 

This strategy, predictably, failed miserably. The Cubs got off to a brutal 2-7 start to the season, losing all three series of their opening road trip in Texas, Atlanta, and Milwaukee. The club did show some signs of life in the following weeks, winning twenty-three out of the next thirty games, to reach a record of 25-14.

The ‘19 Cubs were a dysfunctional and out-of-sync team, and after their strong run in April and early May, they played .500 baseball for the next few months, never able to reach their full potential. In an effort to repair the flaws of the roster that should have been dealt with in the previous offseason, the Cubs signed free agent closer Craig Kimbrel on June fifth, and traded for outfielder Nicholas Castellanos at the trade deadline.

Kimbrel struggled in his first year as a Cub, but Castellanos was absolutely fantastic during his brief stint on the North Side. The right-fielder mashed 16 homers and posted an OPS of 1.002 in 51 games as a Cub. While Castellanos was certainly a boost for the Cubs, their ‘19 season was destined to fail, even with the added spark of their new middle-of-the-order bat.

In spite of their mediocre play throughout much of the season, the Cubs found themselves in the thick of a division race in mid-September. After an 8-2 victory over the Cincinnati Reds on September 16th, the Cubs stood at a season-best fourteen games above the .500 mark.

In their typical one-step-forward-two-steps-back manner, the Cubs would then lose their next nine consecutive games, including an utterly embarrassing four-game sweep at Wrigley Field by the Cardinals. The Cubs finished just six games over .500, at 84-78, and did not qualify for the postseason for the first time since 2014.

A franchise that had reached the top after building its way from the abyss of a century of losing had again found itself at rock bottom. The last drops of euphoric contentment that had been borne from a magical championship run were now finally, entirely, gone.

The Reckoning

So, what now? Where do the Chicago Cubs go from here? If their window of contention is to be salvaged, time is running out. Superstar infielders Kris Bryant and Javier Baez will both reach free agency following the 2021 season, pending any possible, yet seemingly unlikely, contract extensions. Much of the core is either aging or due for a substantial payday, so the Cubs will be forced to make a number of changes sooner rather than later. The Cubs will likely look to retool their roster by shuffling the deck and bringing in some new faces and proven veterans in 2020 and ‘21, attempting a last-ditch run at recapturing their former glory. Only time will tell what is in store for a franchise that is now truly at a crossroads.

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