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Chicago Cubs prospects complicating free agent decisions on veterans

The Chicago Cubs were bold in their trade deadline moves this year, trading no. 2 prospect Jefferson Rojas and top first base prospect Jonathon Long, as well as a number of other Top 30 assets in the organization.

Some young talents, however, were clearly off-limits. And those off-limits prospects could complicate things when it comes to the front office’s decisions on current free agent-eligible major leaguers.

Of the Top 5 prospects in the organization, according to the updated MLB.com rankings, three are outfielders and one is a catcher. At the same time, the big league Cubs are facing a situation where two veteran outfielders and a veteran catcher are heading into free agency at the end of this season.

Chicago has big decisions to make when it comes to corner outfielders Ian Happ and Seiya Suzuki and catcher Carson Kelly. All three are 30-something and will be looking for big-money multi-year contracts. But just 1-3 years away, however, are top-notch talent who are expected to fill those roster spots nicely.

Owen Ayers making Carson Kelly expendable?


Nov 9, 2025; Mesa, AZ, USA; Chicago Cubs catcher Owen Ayers during the Arizona Fall League Fall Stars Game at Sloan Park. Mandatory Credit: Mark J. Rebilas-Imagn Images

Owen Ayers, the team’s 19th round draft pick in 2024, has shot through the Cubs organization so quickly that there’s already talk he could be brought up to the majors when rosters expand on September 1.

It was well-reported that teams had expressed plenty of interest in the 25-year-old at the trade deadline as an asset with a tremendous upside and a history of success everywhere he’s played.

“I’m super grateful I’m still here,” Ayers told Tommy Birch of the Des Moines Register, after the MLB trade deadline came and went. “I love this organization. This is where I want to play. And I want to play at Wrigley Field, so I’m very happy to still be here.”

Ayers has excelled on both defense and offense and will still need some work on the finer points of pitch calling and handling a staff, but there is definite big league potential in him.

His rise could make Carson Kelly expendable, even though Kelly still brings more to the table than the less experienced Ayers.

Outfield of the future vs. Outfield right now


Mar 24, 2026; Mesa, Arizona, USA; Chicago Cubs first baseman Josiah Hartshorn against the New York Yankees during spring training at Sloan Park. Mandatory Credit: Mark J. Rebilas-Imagn Images

Meanwhile, the Cubs have a trio of top-tier outfield prospects who are pegged for Wrigley Field in 2028—No. 1 Josiah Hartshorn, No. 3 Ethan Conrad, and No. 4 Kane Kepley. The three are in the lower tiers of the farm system, but they’re all displaying advanced ability and should move up quickly. The 19-year-old Hartshorn, especially, has showcased some elite-tier talent that has seemingly surprised even the Cubs’ own scouts.

Would the Cubs be willing to re-sign Happ and/or Suzuki to a five-year, $95 million+ deal if they know that these young stars could be major-league ready in two years (or less)? Likely, not.

The question, though, is what the Cubs would do next season with holes to fill in left field, right field, and at catcher while waiting on their minor league talent to develop. Would this be where Matt Shaw and Pedro Ramirez step into corner outfield roles and Miguel Amaya takes the full starting catcher spot?

Having good, young talent on the rise is a nice problem to have. But, in this case, the timing of the rise versus the veterans on the outs may make for some tough decisions this offseason.

This article first appeared on ChiCitySports and was syndicated with permission.

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