After playing a key role in the Red Sox’s two World Series wins, Jed Hoyer joined the Chicago Cubs and helped break their championship drought in 2016. However, the Cubs haven’t made it back to the World Series since, and their last playoff victory came in 2017.
This has led to speculation about Hoyer’s future with the team. Chicago just snapped a four-year playoff drought, but despite back-to-back winning seasons, Hoyer hasn’t built a team with at least 85 wins since 2018.
There’s optimism that could change this year. The Cubs are strong favorites to win the NL Central, with some projections predicting 85 or more wins. Their potential win total could rise even further if they acquire All-Star third baseman Alex Bregman, as Hoyer and the Cubs’ front office are currently negotiating with agent Scott Boras.
Hoyer, who has been with Chicago since 2012, is also in the final year of his contract. Despite being widely regarded as one of MLB’s top executives, his future with the Cubs remains uncertain.
According to Bob Nightengale of USA Today, there have been no discussions between the Cubs and Hoyer about an extension ahead of the 2025 season. His fate appears to hinge on the team’s success this year—winning the NL Central would likely earn him a new deal, but if the Cubs’ playoff drought continues, the franchise is expected to move on from him this winter.
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If Hoyer is let go, he would likely land another opportunity quickly as a three-time World Series champion. Meanwhile, the Cubs’ front office role would be an appealing job, though top candidates may have concerns about ownership’s financial commitment, especially after claims of financial losses in 2024.
Despite some uncertainty about future spending, the Cubs’ top-10 farm system and young core still make this a highly attractive position should Hoyer’s tenure come to an end.