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The 2026 Trade Deadline Could Doom the Chicago Cubs For Years to Come

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Jed Hoyer was unintentionally called out publicly by Bruce Levine in July, and, unwilling to go down silently for a second consecutive year, the Chicago Cubs made aggressive moves at the trade deadline. Desperate for pitching, the organization traded away six prospects for three pitchers who ultimately contributed down the stretch and made the Wild Card roster against the San Diego Padres. However, after an embarrassing sweep, those trades look bad, and they could doom the Cubs for years to come.

Kevin Gausman made nine starts for the Cubs. The veteran right-hander posted a 4.83 ERA in 50.1 innings. The Cubs went 5-4 in those games, and although his overall numbers were poor, Gausman had only two bad outings: 6 ER in 4 IP vs. the Milwaukee Brewers on Sept. 9 and 6 ER in 4.2 IP vs. the Washington Nationals on Aug. 13, resulting in a 3.24 ERA in his other seven starts.

Unfortunately, in his final regular-season start, Gausman injured his left shoulder while making a lunging tag near third base. He wasn’t 100% for his Game 2 start against the Padres on Wednesday night, and although it wasn’t a total disaster, Gausman needed to be nearly perfect to give the Cubs a shot. The right-hander gave up two runs in the second inning and was charged with a third run after Gavin Sheets took Daniel Palencia deep in the fourth with an inherited runner on base.

The Cubs traded Brett Bateman and Ty Southisene to the Toronto Blue Jays for Gausman. Southisene is a 21-year-old, light-hitting infielder whom the Cubs drafted in the fourth round in 2024. He’s still in High-A Ball. Bateman, 24, made an immediate impact for the Blue Jays this year, posting a 138 wRC+ and 1.9 fWAR in 41 games.

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Of course, Bateman wasn’t going to move Pete Crow-Armstrong off center field, and if he had stayed in the Cubs organization, he would have needed to hit for much more power to stick in the corner outfield. Still, batting .329/.402/.424 in 181 plate appearances gives you pause about whether he could have contributed in the future with the Cubs.

Keep in mind that the Cubs will have left field and right field open heading into the offseason as both Ian Happ and Seiya Suzuki will be free agents.

Bateman posted a .410 BABIP, and his batted-ball data show he massively overachieved in his first stint in the majors. Yet that won’t stop fans from checking in on how he continues to perform for the Blue Jays.

Ryan Zeferjahn looked very average for most of his time in the Cubs bullpen, posting a 4.50 ERA over 18 innings. His strikeout rate was 23.8%, which was fine, but opponents hit .268 against him, and the righty had a 10% walk rate. Zeferjahn didn’t get many clean innings, which didn’t give fans much confidence, even though he ended the season with seven straight scoreless outings, including 1.1 innings against the Padres.

He has nasty stuff, throws in the high 90s, and is under team control through 2030. Zeferjahn can obviously take his game to the next level, but as we’ve seen far too often, relievers can be extremely volatile year to year. That’s why it was a little scary when the Cubs traded Moises Ballesteros and pitching prospect Mason McGwire to the Los Angeles Angels for Zeferjahn.

To be clear, this one hasn’t looked bad for the Cubs just yet. Ballesteros had a great month to start the 2026 season, but he couldn’t adjust to MLB pitching afterward, and his slump led to a demotion in June. After the trade, Ballesteros played in 45 games for the Angels. The left-handed batter posted a slash line of .199/.260/.280 with three home runs in 177 plate appearances. The 22-year-old had a 26% strikeout rate and rated poorly defensively at catcher.

But he is only 22-years-old with a history of great bat-to-ball skills. As for McGwire, he was having a breakout season in the Cubs farm system before the trade, and if he ever becomes an MLB arm, that would definitely sting, since the Cubs have a bad track record of developing pitchers.

This is the trade Cubs fans dread most. Clay Holmes was one of the most sought-after starting pitchers at the trade deadline, and Hoyer paid a high price for the veteran righty. Holmes made nine starts with the Cubs, including a 1.55 ERA over five games in August. However, he struggled in September, allowing 18 earned runs in 19.2 innings. His 8.24 ERA, to go along with a 16.1% walk rate, made Holmes so untrustworthy that, despite being on the Wild Card roster, Counsell avoided using him in either game in San Diego.

The trade to acquire Holmes also included outfielder Tyrone Taylor, who was great in his two months with the Cubs, but giving up top prospect Jefferson Rojas could be the biggest mistake Hoyer made in 2026.

The infielder was having a solid year in the Cubs farm system, posting a .799 OPS and hitting 15 home runs in 91 games. If not No. 1, Rojas was certainly top two in most Cubs prospect rankings, and once he joined the New York Mets minor league system, his stock rose even higher.

Rojas finished the regular season with 12 home runs in 34 games in the Mets’ farm between Double-A and Triple-A, slashing .293/.346/.629 over 160 plate appearances.

Maybe the Cubs re-sign Holmes, and he helps stabilize a shaky starting rotation heading into 2027. However, it’s hard not to think the Cubs are on the wrong side of a PCA-type trade that coincidently involved the Mets trading away a future star.

Aldo Soto
Aldo Soto
With a journalism degree from Eastern Illinois University and a decade of Cubs reporting, my work has appeared on 670 The Score, ESPN 1000, and the Pinwheels and Ivy Podcast. I cover Cubs news and analysis for Sports Mockery, including roster moves, game breakdowns, and prospect development.

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