Did the Cubs Actually Make a Huge Trade Deadline Mistake?

As the trade deadline inched closer, the Chicago Cubs had no choice. They were considered one of the handful of teams in baseball to have a genuine shot at a World Series run. If Jed Hoyer chose to sit on his hands and not drastically improve his starting rotation, fans would have greeted him at Wrigley Field with tomatoes.

The Cubs' lead executive proceeded to make several aggressive moves. He added multiple starting pitchers, a thriving reliever, and even a position player to platoon in left field. It was the kind of deadline that turned tomatoes into flowers ... for at least a few weeks.

Chicago would go on to face a swift and borderline embarrassing exit from the postseason. Stealing the top Wild Card spot, the San Diego Padres used their home-field advantage to surge past the Cubs. Craig Counsell's team mustered only a single run over the two games, while his pitching continued to let him down.

Hindsight is always 20/20. It is far too easy – let alone unfair – to say that the Cubs should have taken their foot off the gas at the trade deadline. However, that doesn't mean Hoyer's decision-making is void of criticism. He still took a pretty significant risk with one specific deal, and it's the kind that could come back to hurt the Cubs in the very near future.

Should the Cubs Have Kept Jefferson Rojas?

Knoxville Smokies infielder Jefferson Rojas (2) slides away from home plate after being called out during Opening Day for the Knoxville Smokies at Covenant Health Park against the Birmingham Barons on April 3, 2026. | USA TODAY Network via Reuters Connect

The Chicago Cubs made their last big move of the trade deadline with a familiar face. Jed Hoyer has been no stranger to striking deals with the New York Mets over the years, even acquiring David Peterson from the team a couple of months before the 2026 trade deadline.

The two sides would link up again for a trade that sent Clay Holmes and Tyrone Taylor to the North Side. To little surprise, the cost wasn't cheap. Not only was Holmes one of the more highly coveted arms on the market, but he fit particularly well in front of the Cubs' elite interior defense. New York knew this, and it's exactly why they were able to get their hands on Jefferson Rojas.

For years, Rojas was one of the Cubs' top prospects. He worked his way up to No. 2 on the list by the trade deadline, thanks to another fantastic stint in Double-A. The 21-year-old is truly a do-it-all prospect. He is a high-end infielder who has experience playing second, shortstop, and third base. At the plate, he has been rock solid ever since joining the Chicago system in 2022.

Indeed, Rojas has improved each season of his career, and the Cubs only watched him put up better numbers once leaving the organization this season. In his 29 outings with the Mets' Double-A affiliate, Rojas hit .280 with a staggering .929 OPS. He even hit nine homers during that span after hitting 15 in 91 games with the Cubs' affiliate in Knoxville.

The Mets would even go on to promote Rojas to Triple-A at the end of the year. While it was only a six-game sample size, Rojas looked extremely comfortable, recording 8 hits and 7 RBIs in 26 at-bats. He also added three more homers to bring his 2026 total to a career-high 27.

Two days in Triple-A, two home runs for Jefferson Rojas! pic.twitter.com/bY42u001rs
— SNY Mets (@SNY_Mets) September 16, 2026

Rojas isn't the first prospect to go on a heater after a deadline move, and he will not be the last. However, with someone as talented as Rojas, there is a good chance this is more than just a heater. The Cubs obviously know how high his ceiling is, and they were operating under the assumption that he would be part of their future for quite a while.

Yes, the Cubs are set right now in the infield with Dansby Swanson, Nico Hoerner, and Alex Bregman, but there is a world where Rojas proves equally valuable very soon. Throw in the fact that he is a lot younger and has many years of team control, and this is a decision Jed Hoyer could soon regret.

This is especially true when we consider the Cubs might see Clay Holmes walk in a matter of months. Chicago got just 48.2 innings out of the veteran, which included ZERO in the postseason. Again, hindsight is 20/20, but that's not worth a prospect as tantalizing as Rojas.

What makes the deal even harder to stomach is that the Cubs had a similarly iffy trade with their No. 1 prospect last offseason. They moved outfielder Owen Caissie to the Miami Marlins for Edward Cabrera, who had a disastrous 2026 that essentially made him unusable. Chicago is now on the verge of losing both Ian Happ and Seiya Suzuki in free agency. Having someone like Caissie waiting in the wings sure wouldn't hurt right now!

Look, just like players, front offices are going to swing and miss. There is also certainly a world where the Cubs manage to keep Holmes, and he turns out to be a major part of a 2027 success story. At the same time, not all swings and misses are created equal. Hoyer put a lot on the line by giving up on Rojas, and the immediate results feel like striking out with the bases loaded in the top of the ninth.

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