5 worst Cubs trades, signings during Theo's tenure

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Theo Epstein’s run with the Cubs is over, his legacy in Chicago secured.Epstein resigned from his position as Cubs president this week, ending a nine-year tenure that brought the Cubs their first championship since 1908. When he joined the organization nine years ago, he set out to build a culture of sustained success — and accomplished just that, with the Cubs making five postseason trips in the past six seasons.Epstein was the architect of the Cubs’ rebuild, drafting core hitters in Kris Bryant, Kyle Schwarber and Ian Happ, acquiring a face of the franchise in Anthony Rizzo and a future Cy Young Award winner in Jake Arrieta, and securing the best free agent signing in team history in Jon Lester — not to mention Ben Zobrist, Jason Heyward and more.What about the moves that didn’t work out? You can argue expectations for this Cubs group were greater, but in looking back at Epstein’s tenure, it was difficult to come up with a list of sure-fire misses he made in trades and free agency.This goes to show how successful he and his front office have been on the open and trade markets. That said, here are the five worst moves, which sounds harsh considering they're among a list with far many more good ones. Some notable exclusions:-José Quintana: He wasn’t the same pitcher as he was with the White Sox but wasn’t bad in three-and-a-half seasons, all while being durable on a team-friendly contract. The Cubs gave up top prospects to get him, but whether they won the trade or not is a different discussion.-Daniel Descalso: His offensive performance is well-documented, and the Cubs replaced a 2019 All-Star in Tommy La Stella with him. The deal didn’t work out, but it only cost $5 million.

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RELATED: Theo Epstein’s top 5 moves in his Cubs tenure

One of Epstein and Co.'s first moves with the Cubs was trading second baseman DJ LeMahieu to the Rockies with outfielder Tyler Colvin for third baseman Ian Stewart and pitcher Casey Weathers. The Cubs needed a third baseman after Aramis Ramírez hit free agency, and LeMahieu only had 37 big league games to his name. 

It took a few seasons, but LeMahieu became a Gold Glove and All-Star second baseman in Colorado, winning the NL batting title in 2016. He proved his all-fields, contact approach translates outside of hitter-friendly Coors Field, hitting .336 with a .386 on-base percentage the past two seasons with the Yankees.

Stewart didn’t produce offensively in 2012 and only played 55 games. He spent 2013 in the minor leagues, tweeting the Cubs were letting him “rot” and “might as well release" him, which they did soon after.

The Cubs won a ring without LeMahieu, and while it’s hard to say whether he would have become the same player he is today in Chicago, this is one clear miss.

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Epstein admitted in October 2014 the Cubs wouldn’t do this deal again and that it was a mistake. The Cubs signed Jackson to a four-year, $52 million deal in January 2013. He was only 29 years old and durable, having made 30 or more starts the previous six seasons.

The Cubs were still a few years away from contending, so Jackson was an experienced rotation arm to eat innings and bridge the gap through the rebuild. If he pitched well, they could have flipped him for assets.

Jackson struggled with the Cubs, going 14-33 with a 5.58 ERA and 1.541 WHIP from 2013-14, making 31 and 27 starts. By the time the Cubs’ playoff window opened in 2015, he was exclusively a reliever. The Cubs released him midseason that year and were on the hook for the final season-and-a-half of his deal, worth about $15 million.

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The Cubs had two rotation holes to fill in the 2017-18 offseason (Jake Arrieta, John Lackey) and filled one of them with Chatwood on a three-year, $38 million deal. The Cubs were enticed by his high velocity, sharp curveball, and spin and ground ball rates, and he fared better on the road with the Rockies than at home.

Chatwood kept his walks down to a manageable rate in Colorado but struggled immensely in this area in 2018 (8.2 walks per nine innings) and lost his rotation spot. Chatwood and Yu Darvish struggled in 2018, leading the Cubs to acquire Cole Hamels and pick up his $20 million option for 2019.

Chatwood’s command and performance improved in 2019, but he was almost exclusively a reliever making $12.5 million. He returned to the rotation in 2020 and impressed early, though he only made five starts due to injuries.

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The Cubs signed Morrow to a two-year, $21 million deal in the 2017-18 offseason, and he replaced Wade Davis as closer after an impressive 2017 campaign with the Dodgers (2.06 ERA, 0.916 WHIP, 10.3 K/9 in 45 appearances). The early returns were extremely positive.

Morrow made 35 appearances in 2018, sporting a 1.47 ERA, 1.076 WHIP and 9.1 K/9. He converted 22 of his 24 save chances, slamming the door shut on opponents with a 100-mph fastball. 

July 15, 2018 turned out to be Morrow’s last appearance with the Cubs. He missed the entire second half with right biceps inflammation and underwent a right elbow procedure over the offseason. He experienced setbacks in his rehab in 2019 and was shut down that August, a tough break for the right-hander.

The Cubs signed Morrow to a minor league deal last winter but he shut himself down for the 2020 season after experiencing calf and chest ailments in spring training.

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This move is somewhat here by default, which may go to show how well Epstein did in trades and free agency. The Cubs were in position to sign Kimbrel, available into June 2019 when draft pick compensation wasn’t attached to him, because Ben Zobrist landed on the restricted list (unpaid) due to a family matter.

The Cubs needed an impact late-inning arm and landed Kimbrel on a three-year, $43 million pact. He struggled down the stretch in 2019 and finished the year with career-highs in ERA (6.53) and home runs allowed (nine), along with his highest BB/9 (5.2) since his first big league season in 2010.

Had his season gone differently, the Cubs — who were trying to get under the luxury tax last winter — could potentially have moved Kimbrel for payroll relief.

Kimbrel worked through mechanical issues this past season and bounced back with a 1.42 ERA in his final 14 appearances in a hybrid late-inning relief role. He didn't allow a run or walk in 7 1/3 September innings, featuring his high-90s velocity and sharp breaking pitch. That's a good sign entering the final year of his deal.

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