Following a humbling postseason sweep, Chicago’s front office addresses failed deadline gambles, disastrous bullpen acquisitions, and the urgent roster overhaul needed to salvage the club's championship window.
Chicago Cubs President of Baseball Operations Jed Hoyer held his annual end-of-season press conference on Friday afternoon.
The Cubs were swept in the National League Wild Card Round by the San Diego Padres. The Padres outscored the Cubs 12-1 in that series, and the North Siders went home early after a relatively successful regular season.
Hoyer talked about a wide range of topics at this press conference, including this year’s team, what went wrong, and the future of this organization. Here are three takeaways from his end-of-season press conference.
2026 Season
The Cubs had World Series aspirations this year. That’s a big reason the front office went out and acquired guys like Clay Holmes, Tyrone Taylor, Kevin Gausman, and Ryan Zeferjahn at the trade deadline. This was their all-in move in a year when a deep postseason run was possible.
However, the Cubs fell short of completing this goal. They didn’t come close to the World Series and were eliminated after just two postseason games. Given how aggressive the front office was in acquiring some frontline starters at the deadline, the early exit obviously makes this season a failure.
Both Alex Bregman and Hoyer view it that way because of how it ended.
“We put resources into this team because we believed in this team,” Hoyer told reporters. “There were long stretches where we looked like we could be a dominant team. We pushed in part because of the injuries that we had during the year. We had to take on a lot of payroll to survive and take on those guys. We believed in this group. We had the best player in baseball. An exceptional position-playing group. We believed in this group, and we fell short. We let this opportunity slip away.”
Bullpen Failure
The Cubs had to completely revamp their bullpen this past offseason. Brad Keller, Caleb Thielbar, Drew Pomeranz, Andrew Kittredge, and Aaron Civale were all free agents at the end of last season.
That forced Hoyer to get creative in revamping this bullpen. The Cubs went on to sign Phil Maton to a two-year deal, re-sign Thielbar to a one-year deal, and sign veterans Hoby Milner and Hunter Henry to one-year deals.
However, those relievers didn’t contribute much for the Cubs in 2026. Maton posted a 6.18 ERA over 27 ⅔ innings before a knee injury sidelined him for the year. Thielbar regressed significantly with a 4.86 ERA. Milner was eventually designated for assignment after an emergency appendectomy, and Harvey pitched just four innings.
“I did a poor job on the bullpen this year,” Hoyer told reporters. “The guys we acquired this winter didn’t produce nearly as well as a year ago.”
Pedro Ramirez/Matt Shaw Bigger Roles
The Cubs have a lot of decisions to make regarding their roster next year. One of the biggest is what the team plans to do at corner outfield. Both Ian Happ and Seiya Suzuki are free agents this upcoming offseason.
After Patrick Mooney of The Athletic reported that the Cubs will not get into a ‘bidding war’ for Suzuki this winter, there’s a strong chance the team will have to find his replacement. Well, it sounds like that replacement could come internally.
Hoyer mentioned in his end-of-season press conference that both Pedro Ramirez and Matt Shaw could see more playing time in 2027. Ramirez/Shaw could start at one or both of the corner outfield spots next season. Ramirez has experience playing the outfield in the minors, and Shaw saw opportunities there this year.
“We can ask more of them going forward," Hoyer told reporters. "We didn’t have to this year, given the nature of our corner outfield. But I think they both can certainly do that. I think we’ll lean on both those guys heavily going forward.”
