5 big mistakes the Chicago Cubs have made in recent years

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.

4. The Jose Quintana trade

It might be time to start calling this "The Dylan Cease" trade, now that he is by far the most valuable player involved. Over his past two seasons, Cease has tossed 349 innings and struck out 453 batters. 2022 was particularly spectacular for the 27-year-old, as he pitched to the tune of a 2.20 ERA in his 32 starts, good enough for a 2nd-place finish in Cy Young voting. Now that he is the clear ace of the White Sox pitching staff, it is pretty safe to say that the Cubs made a colossal mistake by moving him at the 2017 trade deadline.

At the time, the Cubs were in the middle of a World Series hangover, and in need of a solid big-league starter to stabilize their lackluster staff. Jose Quintana seemed like a decent candidate at the time, as he had just turned in four straight seasons where he threw 200 innings and his ERA was consistently in the mid to low 3 range. But Quintana's ability seemed to diminish almost overnight when he went to the North Side of Chicago. He was never that top-of-the-rotation pitcher they were seeking, and they gave up a future ace and a guy with 30 home-run potentials in Eloy Jimenez.

What's even worse is the fact that Quintana found himself pitching for the division rival Pirates and Cardinals in 2022, and he schooled the Cubs in each of his four starts against them.

5. The Contreras deadline situation

This is obviously the most recent Cubs mistake, and it was awkward for pretty much everybody. I think it's safe to say that almost everyone remotely close to the Cubs' orbit predicted he would be traded at the 2022 deadline. For weeks, Contreras had to answer questions about what it would be like to not play for the Cubs and how it feels to be traded by the only team he ever knew. His on-field production even dipped, and the Cubs did little to stop the bleeding because they knew Contreras was a hot commodity.

But when the deadline came and went, Contreras was still on the Cubs roster which was likely more surprising to him than anyone else. After being hung out to dry by the front office with little explanation, it's not surprising that Contreras accepted a 5-year deal with the Cardinals. Although reports later came out that a deal that would have sent Contreras to the Astros was shut down by Houston's ownership, perhaps this would not have even been an issue had the Cubs extended Contreras at some point.