3. Non-tendering Kyle Schwarber
This one hurts so bad. Cubs postseason hero Kyle Schwarber, and generally awesome human being, was not given a contract by the Cubs after the 2020 season. To be fair, Schwarber hit an abysmal .188 during the pandemic-shortened 2020 season. His fielding also continued to decline, and Jed Hoyer's front office decided to non-tender Kyler Schwarber before to the 2021 season. Even though just a year prior in 2019, the left-handed slugger hit 38 home runs and drove in 92 runs.
Since the Cubs cut ties with Schwarber, he has proven that he belongs in MLB. In the last two seasons, the Ohio native has hit 78 home runs for the Nationals, Red Sox, and Phillies combined. Only Shohei Ohtani, Vlad Guerrerro Jr., and Aaron Judge have hit more home runs than him in that span of time. His hitting prowess earned him a $79 million deal from the Phillies before the 2022 season. In his first year with Philadelphia, he set career highs in home runs (48), RBIs (94), and Walks (86) while helping the team reach the World Series for the first time since 2008.
It says a lot that the Cubs thought so low of Schwarber at the time that they were not even willing to hold onto him for the first half of 2021. Had he stayed on the roster, the Cubs likely would have dealt him at the deadline along with Bryant, Rizzo and Baez. In that scenario, at least the Cubs would have got something in return, and Schwarber probably wouldn't have felt like the Cubs were kicking him to the curb.
A first-round pick and fourth overall in the 2014 draft, Schwarber stormed onto the scene in 2015 where he instantly became a mainstay in the lineup. The Cubs made the postseason that year, where Schwarber cranked two famous home runs, one which landed on top of the scoreboard at Wrigley Field, and another off Garrett Cole that landed in the Allegheny River in Pittsburgh.
After suffering a torn ACL in an outfield collision with Dexter Fowler, Schwarber missed most of the historic 2016 campaign but miraculously returned to face Cleveland during the World Series. Although he didn't hit any home runs, Schwarber got on base 10 times while playing DH in the road games. In the 10th inning of game 7, he got on base and Albert Almora Jr. pinch ran and wound up scoring the go-ahead run that led to the historic championship.
Ironically, the Cubs are currently in need of a power-hitting left-handed bat. I like to think that if the universal DH was in place in 2021, the Cubs would have held onto Schwarber, and he would still be sending missiles into the bleachers.