Unpacking the pivotal 2021 trades that transformed the Cubs' roster, yielding stars like Pete Crow-Armstrong and setting the stage for future dominance.
The Chicago Cubs took significant strides forward as a franchise in 2025. After a few years of mediocrity, the Cubs finally took that next step.
Before making the playoffs in 2025, Chicago had a few rough seasons in a row. Following a playoff loss to the Miami Marlins in the shortened 2020 season, the team went four consecutive years without a playoff appearance.
In both 2021 and 2022, the Cubs weren’t a competitive organization. They finished below .500 in both of those seasons, and the 2021 campaign officially marked the start of a major rebuild for the organization.
That’s the season when the front office decided to trade away Kris Bryant, Javier Baez, and Anthony Rizzo at the deadline. Even in the offseason prior to the start of the year, the Cubs traded away their ace in Yu Darvish.
But those specific moves have set up the Cubs for 2026 and beyond. Although the North Siders didn’t get any relevant players in the Bryant deal, they did acquire notable players in the Baez, Rizzo, and Darvish deals that year.
Chicago traded Baez and pitcher Trevor Williams for Pete Crow-Armstrong. Crow-Armstrong wasn’t even the Cubs’ preferred target in trade negotiations. But the front office eventually agreed on him after the Mets wouldn’t deal prospects like Francisco Alvarez and Brett Baty.
Fast forward four years, and Crow-Armstrong is coming off a breakout campaign with the Cubs in the Major Leagues. He hit .247 with 31 home runs, 95 RBI, and 35 stolen bases while playing Gold Glove defense in center field.
For Rizzo, prospect Kevin Alcantara headlined the return for the Cubs. While Alcantara hasn’t gotten many opportunities to show his potential in the Majors, he figures to be a key part of Chicago’s future. He is just 23 years old and should have a spot on the Major League roster in 2026.
Then, there’s the Darvish trade that took place in December of 2020. The Cubs received five players in that deal, including outfield prospect Owen Caissie.
Caissie was just selected in the second round of the 2020 MLB Draft, so there weren’t any Minor League numbers to go off of. But the Cubs lucked out by acquiring the Canadian native in this deal.
Caissie is a popular breakout candidate among analysts this upcoming season following multiple strong years down in the Minor Leagues. With Kyle Tucker expected to leave in free agency, the Cubs’ top prospect should see more consistent at-bats in 2026.
Looking back at the 2021 season, the three separate trades involving Baez, Rizzo, and Darvish have set up the Cubs well for 2026 and beyond.
Crow-Armstrong and Caissie figure to be important parts of the organization for years to come, while Alcantara has the potential to be an everyday outfielder after next season, when Ian Happ and Seiya Suzuki are set to be free agents.
It was the right time to trade that core of players, and Jed Hoyer did a great job getting young talent that would help the team in the future.