The curse breaking team that won hearts all around Chicago during the 2016 baseball season is slowly becoming a distant memory. The Chicago Cubs are coming off a disappointing 84-78 season. After the Cubs won 103 games and broke their 108 year World Series title drought, fans believed they would go on to establish a dynasty to reign over the National League for years to come. At the time of the World Series, they had the reigning NL MVP 24 year old Kris Bryant at third base, a 26 year old Anthony Rizzo at first base, a 23 year old second baseman named Javier Baez, a 22 year old Addison Russell playing shortstop, and a 23 year old Wilson Contreras behind the plate. This was a young core of position players envied by teams throughout the league. They also had a 22-year-old Kyle Schwarber who came off of ACL surgery to post a .971 OPS in the World Series and a 24-year-old Jorge Soler just four years removed from inking a 9-year contract for 30 million dollars to come over from Cuba. Kris Bryant, Javier Baez, Addison Russell and Kyle Schwarber were all former first round picks while Jorge Soler was one of the most highly touted Cuban prospects to defect at the time. In addition to this talented group of younger players, they had a rotation led by stalwart Jon Lester and co-ace Jake Arrieta, 32 and 30 years old respectively, still in their prime even if it was the second half of their respective careers.

In 2012, the Cubs committed the baseball equivalent of a highway robbery by trading Andrew Cashner and Kyung-Min Na to the Padres for Anthony Rizzo and Zach Cates. Kyung-Min Na and Zach Cates never had much of an impact in the Major Leagues, so the trade came down to Andrew Cashner and Anthony Rizzo. Andrew Cashner had two nice years for the Padres posting a 3.09 era in 2013 and a 2.55 era in 2014, but he never developed into the front of the rotation starter the Padres were hoping for. Finishing with a 3.67 era in San Diego and an ERA+ of 98, he was eventually traded to the Miami Marlins during the 2016 season. However, Anthony Rizzo has spent eight successful seasons playing for the Cubs: posting an .872 OPS to go along with 217 home runs in 1158 games played. He has been top 10 in MVP voting 3 times, won three gold gloves at first base, and was an integral run producer and leader on the young Cubs championship team. In 2013, the Cubs pulled off their second heist: acquiring Jake Arrieta and Pedro Strop for Scott Feldman and Steve Clevinger. Scott Feldman had been good for the Cubs (posting a 3.46 era in 15 games), but that era rose to an unsightly 4.27 as an Oriole. He left that team after one season to sign a 3-year deal with the Houston Astros. Steve Clevinger was never able to make it in the Major leagues as a starting player and, just two years after playing in 69 games in Baltimore over three years and posting a .680 OPS, he found himself out of professional baseball. After being a top prospect in Baltimore’s system prior to the 2010 season, Jake Arrieta struggled to the tune of a 5.46 era in Baltimore from 2010-2013. However, once traded to the Cubs in 2013, he immediately righted the ship and posted a 2.73 era and a 157 era+ with 793 strikeouts in 803 innings. Some believed this breakout was destined to happen eventually; it looks like the Cubs just found the switch to finally transition it into reality. Arrieta managed to win the Cy Young in 2015 after recording a league leading 22 wins, a 1.77 ERA, and 215 ERA+ in 229 innings. He also led the National league in shutouts with 3, complete games with 4 and over a strikeout per inning. While Jake Arrieta does have an impressive 3.08 career postseason ERA his most impressive performances came in the 2016 World Series where he won game 2 and game 6 to finish with a 2.38 ERA and 15 strikeouts in 11 innings. Pedro Strop was also very productive as a Cub: posting a 2.90 ERA, a 141 ERA+, and 425 strikeouts in 373 innings in the regular season. He also has a career 1.86 ERA with 14 strikeouts in 22 career postseason innings with the Cubs and Orioles.

In 2015, the Chicago Cubs signed Jon Lester for six years at 155 million dollars. Many believed signing him to this deal after they had won just 73 games in 2014 was a big jump the team was not ready to take. Instead, it was the turning point for a franchise drowning in decades of losing. This free agent signing, and the previous two great trades helped Theo Epstein, the Cubs President of Baseball Operations, and Jed Hoyer, the Cubs general manager, cement themselves in baseball “front office” history.

There was one last trade that happened before the 2016 season that was instrumental in the construction of the Cubs championship roster. The Cubs traded Ryan Dempster to the Texas Rangers in 2012 bringing back Christian Villanueva and Kyle Hendricks. While Christian Villanueva never played for the Cubs and only managed 122 career games with the Padres, Kyle Hendricks has posted a 3.14 ERA in 6 years with the Cubs. He also has a career 2.98 ERA in the postseason and a 1.00 ERA in 9 world series innings in 2016. He has been the solid number three starter the Cubs have needed behind Jon Lester and Jake Arrieta since he arrived giving them solid innings and ratio stats. They also signed utility man Ben Zobrist to play second base for them in 2015, even though he would eventually man left field in the 2016 postseason. They flipped Starlin Castro, their incumbent second basemen, that same year to the Yankees for Adam Warren and Brendan Ryan. Along with these four big moves before the 2016 season, at the trade deadline the Cubs made the move that many believe put them over the top for their first championship in 108 years, but others criticize as the beginning to their downfall. The Cubs believed they had the championship roster of 2016 and went all in, trading top prospect Gleyber Torres along with prospects Billy McKinney and Rashad Crawford and relief pitcher Adam Warren. While Aroldis Chapman did collect 4 saves in the 2016 postseason he only collected one in the world series and blew game 7 though it was no fault of his own as Manager Joe Maddon had overused him up to that point in the postseason.

The trade of Gleyber Torres was the starting point of the fall of the Chicago Cubs. While Gleyber Torres came up through the Cubs system as a shortstop, many believed he could play shortstop or second base. Even so, the Cubs believed their middle infield (of both the present and future) was figured out with Javier Baez, Addison Russell, and Ben Zobrist. While Ben Zobrist has been productive throughout his four years as a Cub, he only played 47 games in 2019 and is now 38 years old. Now, the good part is Javier Baez has developed into the player many thought he would be when the Cubs drafted him back in the first round of 2011. After not posting an OPS above .750 during his first three years in the big leagues, he has turned into a homerun threat hitting 23, 34, and 29 home runs respectively over the last three years. He also has been regarded as the best second base defender and one of the top shortstop defenders in the league. Unfortunately, Addison Russell has not developed as everyone has hoped. As a prospect, scouts loved his quick hands both at the plate and in the field. Many believed he would be a high average hitter with average or above average power for a middle infielder. Addison Russell has thus far disappointed as he has never had an OPS above .740. In 2019, he served a domestic violence suspension and was cut by the Cubs. Javier Baez has shifted over to shortstop but right now there is no long-term answer at second base, a position Gleyber Torres played for the Yankees last year. Torres posted an .871 OPS last year with 38 home runs and looks like he is just getting started on a superstar career. Despite the Cubs top prospect Nico Hoerner being the potential future second baseman, his potential is not even close to being near Gleyber’s. No one could have foreseen that Addison Russell would not develop, but he isn’t the only one who didn’t deliver like people had hoped. After tearing up the Indians pitching in the 2016 World Series, and being one of the only men on the planet who could hit Andrew Miller that year, Kyle Schwarber has not become the hitter everyone hoped for. While he did post an .871 OPS in 2019 with 38 home runs, he only had a .250 average and got caught stealing three times with a record of only stealing two bases successfully. Schwarber is a converted catcher, so speed will never be part of his game, but he has a career -9 defensive runs saved, meaning he contributes no additional value on the defensive side of the ball either. He also is seen by some as a platoon hitter since he hits righties at a much better rate than lefthanders. The Cubs thought they had found their long-term middle infield and left fielder; instead, they may have a platoon hitting designated hitter they are forced to play in left field and a shortstop with no double play partner. These wouldn’t be such glaring problems if they weren’t compounded by the other bad moves made by Epstein and Hoyer.

In February 2018, the Cubs signed Yu Darvish to a six-year $126 million contract in response to losing Arrieta after the 2017 season. Darvish was coming off a solid season for Los Angeles and Texas, even though he got lit up in the world series by a cheating Houston Astro team. Since he has joined the Cubs, he has posted a 4.16 ERA with a 4.30 fielding independent pitching (FIP) despite 278 strikeouts in 218 innings. While he was much better in the second half of 2019, Darvish has a long way to go to make this contract look like a good investment for the Cubs. Now there was one deal that was signed in December 2015 that helped the Cubs win the world series but also looks like a disaster today: Jason Heyward was given a $184 million contract for 8 years in right field. They had a good, young infield core and felt they could spend money on the outfield to make their team more well balanced. While Heyward was a great defender in his first few years in Chicago, and supposedly gave a great speech to the team during the 2016 World Series game 7 rain delay that some argued pushed them to victory, he has not hit since joining the northsiders. He posted his highest average for the Cubs in 2018 at .270 and his highest home run total and OPS in 2019 at 21 and .772 respectively. He has also lost a step in the outfield and is no longer a gold glove defender. While his stats are above replacement level, and his glove keeps him in the lineup, the money the Cubs dished out for him is constraining the team as it attempts to go into the future. The final straw that may have broken this “billy” goat’s back could be the Jose Quintana trade. While Quintana never had an ERA above 4 for the White Sox up until 2017, he has never posted one below four in a full season for the Cubs. The Cubs acquired Jose Quintana in exchange for top prospect Eloy Jimenez, Dylan Cease, Matt Rose and Bryant Flete. Eloy Jimenez was the Cubs top prospect and seen as a leftfield prospect with great raw power. Dylan Cease could be a future ace or great number two. In his rookie season, Eloy Jiménez .828 OPS in 2019 and hit 31 home runs. While Kyle Schwarber produced better stats last year this could only be the tip of the iceberg for Jiménez while I wonder if Schwarber could ever get better due to his struggles against left handed pitching. While neither Jimenez nor Schwarber is a great fielder Jiménez is over three years younger than Schwarber, doesn’t have a major surgery on his knee, and is just beginning to tap into his raw potential. While Dylan Cease did post a 5.79 ERA last year, his FIP was only 5.19. That may not sound much better, but it does mean Cease still has the great raw talent he had as a prospect and there is a learning curve for each pitcher in the MLB. One thing the Cubs are currently short on is young starting pitching as Tyler Chatwood, their youngest starter at age 30, who has a career 4.38 ERA. The only Cubs pitching prospect that looks like he will be ready to contribute in any meaningful way is Brailyn Marquez.

The Cubs do not have the future they once had after trading so many key top prospects in recent years and it looks like their once young inexpensive core is starting to show some troubling trends. Even though Theo Epstein, Jed Hoyer and Joe Maddon are revered in Chicago for breaking the 108 year curse, they all have their own flaws and due to many missteps the Cubs look like a shell of the team that won the 2016 World Series. The team spent their money poorly, their players didn’t develop like they had hoped, and they have little coming up through the farm system. Joe Maddon left after the 2019 season to manage the Angels and was replaced by David Ross a member of the 2016 World Series team but he is a manager with no experience. If Yu Darvish can continue pitching the way he did at the back end of 2019, if Jose Quintana can regain his form from the south side, and if Jason Heyward can hit just enough that his value doesn’t solely rely on his defense, then maybe the Cubs have one more run in them. Still, the Cubs have already looked to trade Kris Bryant this past offseason as he will soon be a free agent, Anthony Rizzo isn’t getting any younger, and their pitching staff badly needs an injection of young blood. They also just signed closer Craig Kimbrel to a three-year deal and even the future hall of famer doesn’t look like who he once was, posting a 6.53 era in 2019 well above his career 2.08. Maybe the Cubs can trade Bryant or Wilson Contreras’s backup Victor Caratini for some young pitching, but if that doesn’t happen the Cubs could be looking ahead at some more long years without another World Series championship.