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The Cubs Built for October. Now Comes the Part That Counts.
Records current as of Aug. 26, 2026
The Cubs are 76-57, second in the NL Central behind Milwaukee, and holding a comfortable position in the National League wild card race. Going into the Crosstown series, they had the fourth-best record in the National League and the fifth-best in baseball, and FanGraphs put their playoff odds at 97.9%.
The regular season, in other words, is largely settled. What isn’t settled is whether this team is built for the thing that ended their 2025.
Last October is the context for all of it
The Cubs made the playoffs last year, beat San Diego two games to one in the Wild Card Series, and then lost a five-game Division Series to Milwaukee, three games to two.
That’s a good season by any normal standard and an unsatisfying one given the expectations. Chicago has operated at championship-or-bust level since spring, and Jed Hoyer’s front office spent the deadline making sure the roster wouldn’t fail in October for the same reason it failed in 2025.
The deadline was about arms
The offense has been among the best in baseball all year. The pitching staff spent the season scrambling — a long list of rotation injuries left the depth stripped thin at times, and the group held the line anyway.
Hoyer’s response was to add four pitchers: Kevin Gausman from Toronto, Clay Holmes from the Mets, Braxton Garrett, and reliever Ryan Zeferjahn, plus outfielder Tyrone Taylor in the Holmes deal.
Gausman brings the thing you can’t acquire in September: more than 56 innings of playoff experience, including two starts in last fall’s World Series for the Blue Jays, who lost a seven-game classic to the Dodgers. His ERA sits at 4.38 and his underlying numbers are essentially in line with his career norms. Craig Counsell’s read went past the statistics — a dependable, battle-tested arm that nothing is going to rattle.
His first three starts in Chicago have been rocky: 1-1 with a 6.19 ERA over 16 innings, with 16 strikeouts and four walks. Small sample, but worth watching.
Holmes is the more interesting fit. He posted a 2.39 ERA in nine starts for the Mets before a leg injury, carries a 3.26 ERA over two seasons since moving into the rotation, and — critically — generates ground balls at a rate only a handful of pitchers in baseball can match.
That matters more for the Cubs than for almost anyone else, because Chicago has the best defensive infield in baseball. Dansby Swanson, Nico Hoerner, Alex Bregman and Michael Busch behind a ground-ball pitcher is the kind of fit front offices dream about. David Peterson, acquired from the Mets in June, already demonstrated what this defense does for a pitcher in a six-start sample.
Holmes also has a 1.35 ERA across 20 playoff innings from his high-leverage relief days with the Yankees, including five games against the Dodgers in the 2024 World Series.
Taylor was added for a narrower reason: he hits left-handed pitching, which lets Counsell reduce Ian Happ’s at-bats against lefties down the stretch.
The Milwaukee problem, and the Los Angeles one
Milwaukee sits at 81-51 and has been the better team all year. The Cubs may not catch them, which likely means a wild card round rather than a bye — the same path that led to last year’s early exit.
Beyond that, Hoyer has been direct about the actual obstacle. The Dodgers have won two championships in a row, have the most talent in baseball, and are the team standing between everyone else and a World Series. Chicago’s deadline was constructed with October in Los Angeles in mind, not just September in the Central.
What to watch over the final month
- Gausman finding it. Three uneven starts don’t change the trade’s logic, but the Cubs need him right by late September, not hoping he arrives in the postseason.
- Holmes’ workload. He’s back from a leg injury and building up. How Counsell manages his innings now determines what’s available in October.
- The infield defense holding. It’s the team’s structural advantage and the reason the pitching additions fit. It has to stay intact.
- Seeding. Catching Milwaukee is a long shot, but the difference between a bye and a wild card series is the difference between two playoff formats.
The Cubs were winning at roughly a 91-win pace before the deadline and made themselves better. That’s a good place to be on Aug. 26. It was also a good place to be last August.
Chicago Sports Wire covers Cubs news, schedules and game coverage all season. See the Cubs schedule for first pitch times and broadcast info, or the NL Central standings for the current race.