2021 Trade Deadline Has Proven To Be Complete Disaster for Chicago Cubs

The Chicago Cubs pulled off a trade to supplement their bullpen depth on Thursday, acquiring a promising reliever from the San Diego Padres.

With that news also came the announced DFA of Caleb Kilian, one of the return pieces in the infamous Kris Bryant trade that took place ahead of the 2021 deadline.

That year was the demarcating line for this franchise.

The front office decided to break up the core group of players who helped the Cubs end their World Series drought in 2019, and while it might have been the right thing to do based on how Bryant, Javier Baez, Anthony Rizzo, Craig Kimbrel and others have looked since, it's also fair to point out that this deadline was a complete disaster for the organization.

Since Kilian was designated for assignment, the expectation is Chicago will lose him via a waiver claim or trade within the next week.

If that happens, then both Kilian and Alexander Canario -- the other part of the Bryant trade package -- will no longer be with the Cubs since they traded the latter to the New York Mets in February following his own DFA.

Not having one of the players acquired for the former face of the franchise is inexcusable, but that wouldn't be the first time this has happened regarding a deal that was made ahead of the 2021 deadline.

The Cubs officially got nothing for Kris Bryant and Craig Kimbrel.

Craig Kimbrel Trade:
- Madrigal (non-tendered)
- Heuer (non-tendered)

Kris Bryant Trade:
- Canario (DFA'd)
- Kilian (DFA'd)
— Michael Cerami (@Michael_Cerami) April 10, 2025

Both Nick Madrigal and Codi Heuer were non-tendered and aren't with the organization, a catastrophe when considering Kimbrel was the best closer in the sport during the first half of the season with a 0.49 ERA across his 39 appearances to go along with 23 saves and an All-Star nod.

The deals featuring Rizzo and Baez were more fruitful.

The Mets sent Pete Crow-Armstrong to Chicago in exchange for the slugging shortstop and pitcher Trevor Williams.

Regarding that one, it looks like the Cubs came out on the positive end.

Baez signed a megadeal with the Detroit Tigers after that season and has been a flop. And while Williams has been solid thus far, the ceiling for Crow-Armstrong is being a perennial Gold Glove contender in center field.

Chicago netted Kevin Alcantara and Alexander Vizcaino from the New York Yankees in exchange for Rizzo. Alcantara looks like he could be a future star for the Cubs based on what he's done in the minors, but Vizcaino hasn't appeared in a professional baseball game for an MLB affiliate since 2021, failing to show up in 2022 that earned him a spot on the restricted list.

How Alcantara performs will decide whether or not that trade was a win for Chicago, despite Rizzo executing at just above the league average during his tenure with the Yankees.

Some deals that went a bit under the radar weren't positives for the Cubs, either.

Jake Marisnick was shipped out in exchange for pitcher Anderson Espinoza, a player who only appeared in seven games for Chicago before he was removed from the 40-man roster.

Andrew Chafin was dealt to the Athletics for outfielder Greg Deichmann and pitcher Daniel Palencia. They got some run out of the latter, with him making 37 appearances for the big league club while still being with the organization, but Deichmann played in just 14 games for the Cubs before he was released in 2022.

Joc Pederson was traded to the Atlanta Braves, and not only did he help that franchise win their first-ever World Series that year, but prospect Bryce Ball, who was the return piece, never made it to The Show before he was released.

All in all, what Chicago got back from the 2021 deadline was minuscule.

Crow-Armstrong is the only player currently on their Major League roster and Alcantara is the only prospect who looks like he could be an impact guy for the Cubs at some point in his career.

Trading away the core was the right decision.

But who Jed Hoyer and the organization got back in return was a complete disaster.

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