PEORIA, ARIZONA – MARCH 06: Owen Miller #11 of the Chicago Cubs bats during the fifth inning of the spring training game against the San Diego Padres at Peoria Sports Complex on March 06, 2026 in Peoria, Arizona. (Photo by Jeremy Chen/Getty Images)
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The Chicago Cubs entered the 2026 season with expectations of taking another step toward becoming a legitimate World Series contender, but another early playoff exit has left the organization facing some significant questions.
Ultimately, that could involve some significant roster changes or perhaps a larger organizational overhaul.
“For the second consecutive year, the Chicago Cubs earned one of the National League wild-card spots and for the second straight year, they were unable to parlay the spot into a deep postseason run,” Matt Snyder wrote for CBS Sports. “Something needs to get better.”
That need for improvement could create plenty of movement around the roster, and the Cubs have already lost one depth option to the open market before their additional offseason work could really get underway.
Chicago Cubs Infielder Enters Free Agency Right After Disappointing Season Ends
Veteran infielder Owen Miller elected free agency on Monday, according to the official transaction log.
Miller’s departure came after a season in which he spent most of his time with Triple-A Iowa, with a brief opportunity in the big leagues.
“The Cubs added Miller on a minor league deal over the winter,” Charlie Wright wrote for MLB Trade Rumors. “He spent most of the season at Triple-A Iowa. Miller got a brief look in August. He was on the roster for a series, appearing in one game as a defensive replacement.”
Though the 29-year-old didn’t get much of a big-league audition this winter, he has displayed some key defensive versatility in his career. The former third-round pick has appeared at first base, second base, third base, shortstop and all three outfield positions during his time in professional baseball, giving clubs a potentially useful bench piece even when his offensive production has been inconsistent.
Miller also had a productive season at Iowa, batting .295 with seven home runs, 60 RBI and 11 stolen bases over 413 at-bats.
Chicago Cubs Face More Offseason Roster Decisions
Miller’s free agency is unlikely to be the biggest decision facing Chicago, but it illustrates the type of roster churn that could follow another disappointing postseason.
Before a relatively disappointing season with the Cubs, Miller appeared in more than 300 big-league games combined with the Cleveland Guardians, Milwaukee Brewers and Colorado Rockies. Now, he’ll get an opportunity to find a team that may value his defensive flexibility and minor league production more heavily.
For the Cubs, meanwhile, Miller’s departure opens another spot in an organization that will need to determine which depth pieces belong in the plans for 2027.
After another season that ended sooner than Chicago hoped, even relatively minor roster decisions could become part of a larger effort to finally turn regular-season success into a deeper October run.
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