2 Cubs World Series Champions Jed Hoyer should have extended, 2 he rightly let walk

When the Chicago Cubs finally won it all in 2016, the thought was that they had one of the best young core groups of players in baseball. The team reached the NLCS three seasons in a row from 2015-2017 but only hoisted one World Series trophy in the process, a goal that players from that team will tell you should have been accomplished more than once.

By 2021, the team's core was traded away at the MLB deadline, while some players weren't even tenured contracts for that season. Looking back at the team's core four, did the Cubs make the right moves by not extending these players? Here are two that should have been extended and two that Cub's President of Baseball Operations rightly traded or let walk.

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Cubs that should have been extended: 1. Kyle Schwarber

When the Calendar flipped to 2021, the Chicago Cubs made a shocking decision to non-tender slugger Kyle Schwarber a contact. Looking back, this is one of the more infuriating decisions Jed Hoyer has made, as Schwarber has been one of the most prolific home runs hitters in all of baseball ever since.

Since 2021, Schwarber has hit 32, 46, 47, and so far 24 home runs in those past four seasons. Notably, he would have led the Cubs in homers every year, who haven't had a 30-home-run hitter since 2019. Jed Hoyer and company missed the mark by letting fan-favorite Schwarber walk, as they are still trying to fill the void from losing his power bat in the heart of the lineup.

Cubs that should have been extended: 2. Anthony Rizzo

The Heart and Soul of the Chicago Cubs from 2015-2021 was undoubtedly Anthony Rizzo. After failing to reach a contract extension with the Cubs brass, Rizzo signed with the Yankees after being traded to New York at the 2021 deadline. Keeping Rizzo may have proved beneficial if they could have worked out a higher AAV shorter deal. He is not producing well in 2024, but he hit 26 home runs in 2021 and blasted another 32 in 2022. His 2023 was cut short due to a concussion.

The Cubs, in turn, received bonified top 100 prospect Kevin Alcantara, who they have yet to see debut in the majors. He looks to be someone who will be flipped to help establish the major league roster at this point, as the Cubs' outfield is already packed with Pete Crow-Armstrong, Ian Happ, Seiya Suzuki, and Mike Tauchman off the bench, and that's before the team finds out if Cody Bellinger will opt in for 2025.

Cubs that rightly walked: 1. Kris Bryant

The Cubs did make the right move, moving on from former Rookie of the Year and MVP Kris Bryant. At the time, receiving Alexander Canario and Caleb Kilian was a solid enough haul to at least have the team excited about the future. Still, neither has been able to stick in the majors yet. Still, Bryant has been riddled with injuries in the past few years, appearing in just 159 games over the past three years.

Even worse, when Bryant is healthy, his power has since diminished, launching just 24 homers over those three seasons, which is different from what the Colorado Rockies had in mind when they inked him to a seven-year deal to play in hitter-friendly Coors Field. Regardless of the prospect currency the Cubs received, they certainly are lucky not to be on the hook for anything financially, given how much Bryant's health issues have kept him out of action.

Cubs that rightly walked: 2. Javier Baez

Bryant's situation has been unfortunate due to health issues, but Javier Baez not being extended by the Cubs was a stroke of genius by Jed Hoyer. Baez wanted a contract worth more than $200 million at the time, which would have been highway robbery if he received it. Though Baez was a superstar for the Cubs in 2018 and 2019, he has fallen off since he signed his deal with the Detroit Tigers, slashing just .221/.263/.347 in the past three years. That line worsened as time passed, and he got down to .184/.221/.294 in 2024 before landing on the IL.

The best part about the Cubs trading away Baez was that they received Pete Crow-Armstrong in return, who has swiftly turned the corner in his rookie campaign this season. Crow-Armstrong has all the tools to be an elite-level player in MLB, and it's one of Jed Hoyer's most impressive trades during his tenure with the Chicago Cubs.