The Cubs are heading into a winter full of hard calls, and the pressure to shop the trade market is real. With a weak free-agent class in front of them, Chicago may have to look beyond the open market to patch up the roster. But after getting burned once already, the front office can’t afford another mistake.
Last year’s deal sending Owen Caissie to the Marlins for Edward Cabrera is the warning sign. Caissie had the look of a power bat the Cubs could use right now, while Cabrera didn’t even stick in Chicago’s rotation for the full 2026 season. That’s the kind of swing that can haunt a team, which is why these three prospects should be off limits.
Josiah Hartshorn sits at the top of the list. MLB Pipeline has him ranked as the No. 35 prospect in baseball, and he’s now the Cubs’ top minor leaguer after a huge 2026 season.
Across three levels, the 19-year-old switch-hitting outfielder hit .284/.407/.518 with 23 homers, 26 doubles, 91 walks and 112 RBIs. He brings power, patience and a ceiling that stands out.
He barely reached Double-A last year, so there’s still plenty of development ahead, but Hartshorn has the kind of upside that could make him a difference-maker as soon as 2028. Moving him now would mean giving up on offense the organization may badly need later.
Owen Ayers belongs in the same untouchable conversation. Catchers who can both handle the position and hit are hard to find, and Ayers checked both boxes in 2026.
The 25-year-old put together 55 extra-base hits, including 29 doubles and 25 home runs, while driving in 82 runs and drawing 82 walks over 125 games. Those are huge numbers for a catcher.
Chicago already has Miguel Amaya for the foreseeable future, but Amaya is more of a defensive option and not much of a threat at the plate. Ayers is too valuable to move, especially with Carson Kelly’s future still uncertain.
Then there’s Brooks Caple, who turned himself into one of the most important arms in the system with a breakout 2026. The former ninth-round pick made 21 starts split between South Bend and Knoxville, posting a 3.09 ERA with 108 strikeouts over 107 2/3 innings.
At 24, he should reach Triple-A early next season and could help shore up Iowa’s thin rotation. The Cubs’ farm system is short on starting pitching, and that makes Caple even more important.
Chicago could try to cash in on his value, but doing so would chip away at the kind of depth a pitching staff needs, especially with five major league starters headed for free agency this winter.
In Other News...
Daniel Palencia Is Suddenly A Huge Cubs Bullpen Question
Daniel Palencia entered the season with a chance to keep pushing toward the back end of the Cubs bullpen, but injuries kept interrupting that path and left him with only 32 appearances. An oblique issue and a flexor strain slowed his year, and even when he was on the mound, the results did not match what he had shown in previous seasons. The concern now is less about raw stuff than about whether he can stay available long enough to build momentum again.
Palencias split-finger pitch was a particular problem, with opponents handling it well and forcing a closer look at how he fits in late-inning roles. For the Cubs, that makes his development more than a side note, because a bullpen that needs more certainty cannot afford another arm drifting between promise and uncertainty. He still has a path back to being a trusted high-leverage reliever, but it will require better health and a more dependable third pitch to get there. [Read more 🡒]
Cubs Still Chasing The All-Star Game As Wrigley Tension Builds
The push to bring the 2027 MLB All-Star Game to Wrigley Field is already changing the blocks around the ballpark. Chicago Cubs officials and city crews are moving ahead with more than $32 million in security upgrades tied to the event, including bollards, relocated light poles and a wider sidewalk on Addison, all of it aimed at meeting league requirements before next April.
For the Cubs, the project is part of the price of hosting one of baseballs biggest showcases, with the team covering $8 million of the total. It also underscores how much work still has to be done before Wrigley can welcome the midsummer spotlight, even as the ballparks neighborhood braces for the disruption that comes with major construction and a marquee event on the horizon. [Read more 🡒]
Cubs Bring Back A Familiar Arm As Bullpen Questions Keep Growing
The Cubs have added a familiar name back into the pitching mix, signing right-hander Gabe Klobosits to a new minor league contract as they continue to sort through a bullpen picture that has only gotten more complicated. It is his second year in the organization, and the move brings back a pitcher who already knows the routine in Iowa and has spent time on both sides of affiliated baseball.
Klobosits also comes with a track record that stretches beyond the Cubs, including major league experience with the Nationals and stops in independent ball. His path has not been a straightforward one, with injuries and surgery shaping parts of his career, but Chicago is giving him another chance to work his way back into the conversation. [Read more 🡒]