Cubs’ biggest 2026 MLB trade deadline mistake

The Chicago Cubs are all in this season when it comes to going for a World Series title. Ten years after the Cubs broke their 108-year dry spell by beating Cleveland in the 2016 World Series, manager Craig Counsell may have a team that is capable of winning another championship.

The Cubs made one of their strongest cases of the season as they swept a three-game series against the two-time World Series champion Los Angeles Dodgers at Wrigley Field. They followed up that sweep with a dramatic 3-2 extra-inning victory over the Toronto Blue Jays Thursday. That game saw Alec Bregman tie the game at 2-2 with two outs in the bottom of the ninth inning and Pete Crow-Armstrong score the winning run when he stole third base in the 11th inning and scored when the throw went past the third baseman and into left field.

The Cubs tried to improve their status at the trade deadline. They acquired Kevin Gausman, Clay Holmes and Braxton Garrett in an effort to improve their pitching staff. The Cubs have been beset by pitching injuries this season, and they are hoping that Gausman and Holmes should be able to step into the rotation and solidify that unit.

Came up short in bid for superstar pitcher

However, the Cubs were hoping that they could acquire two-time Cy Young Award winner Tarik Skubal from the Detroit Tigers. He was the prize of the trade deadline and the Milwaukee Brewers, Tampa Bay Rays, and the Dodgers also wanted to acquire his services.

The Dodgers, of course, were successful in that assignment. They had the most assets to send to Detroit and the Tigers selected them as their dance partner.

The Cubs appear to have done well with Gausman and Holmes, but that may not be good enough when it comes to winning a World Series title.

Cubs may regret not making a winning offer to the Tigers

Team president Jed Hoyer and general manager Carter Hawkins are in charge of giving Counsell the kind of roster that would allow them to overtake the Brewers in the National League Central and help them to compete against the Dodgers in the postseason.

While the inclination is for those that failed in their assignment to bring home the top pitcher to shrug their shoulders and say “there was nothing we could do,” that’s not good enough. The Dodgers have the strongest team and the best pitching staff in baseball, so any team that sees themselves in direct competition with them can’t let them get stronger.

It might not have been a mistake if the Brewers or Rays had been successful in acquiring Skubal, but the Cubs could not afford to let the Dodgers win the battle. That team may be in the midst of a six-game losing streak, but they are expected to be at their best when the money is on the table in the postseason. Dave Roberts has a powerful and confident team, and it will require a massive effort to beat them.

The Cubs can say all the right things going forward and can take heart from sweeping the Dodgers in early August. However, it will be difficult for this team — or any team — to have confidence when facing the Dodgers.

Gausman and Holmes should provide an upgrade

Gausman was one of the mainstays of the Toronto Blue Jays pitching staff and they depended on him throughout their postseason run last year.

Gausman is not having his best season in 2026 as he has a 5-10 record with a 4.38 earned run average. The 14-year veteran has made 23 starts with 11 having been labeled as quality starts. He has struck out 127 batters in 127.1 innings, and he has allowed 36 bases on balls while giving up 15 home runs.

However, Gausman was a mainstay for the Blue Jays in the postseason last year. He pitched in 6 games and made 5 starts, and he had a 2-3 record along with a 2.93 ERA in 30.2 innings of work.

The Cubs are hoping that Gausman will be one of the team’s mainstays in the postseason this year.

Holmes has been on the 60-day IL since suffering fractured right fibula after he was struck with a line drive off the bat of Spencer Jones of the of the New York Yankees. However, Holmes appears to be in the final stages of his recovery process and hie is expected to start Saturday when the Cubs face the Royals in Kansas City.

Holmes is a 9-year veteran. He had started 9 games at the time of the injury, and he has a 4-4 record with a 2.39 ERA. The Cubs believe that he can provide some consistency down the stretch.

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