The Chicago Cubs have reached a point in the 2026 season where simply making the postseason is no longer enough.
After spending years building toward the future, Chicago finally made the kind of aggressive moves that signal a team determined to win right now. The acquisitions of Kevin Gausman and Clay Holmes have changed the expectations surrounding the club, and with the Milwaukee Brewers still sitting comfortably atop the National League Central, the Cubs now have a difficult but very real opportunity to close the gap.
Chicago has been playing some of its best baseball at precisely the right time. The Cubs have won five of their last six games, including an impressive sweep of the Los Angeles Dodgers. During that stretch, they have faced some of the game’s toughest pitchers, including Max Fried, Tarik Skubal and Dylan Cease.
Those games carried the intensity of postseason baseball, and Chicago responded accordingly.
Yet despite the Cubs’ strong run, Milwaukee continues to create a major obstacle. The Brewers have been remarkably difficult to catch, leaving Chicago roughly 5½ games behind in the NL Central.
The margin is significant, but it is not insurmountable.
And the Cubs now have something they did not have earlier in the season: a revamped pitching staff capable of giving them a legitimate chance to make a sustained run.
Gausman and Holmes Change the Equation
The Cubs’ decision to acquire Kevin Gausman and Clay Holmes at the trade deadline was about more than adding recognizable names.
It was a declaration.
Chicago is no longer content to wait for prospects to develop or hope another offseason finally brings everything together. The front office made it clear that the organization believes this roster is capable of competing immediately.
Gausman is expected to provide veteran stability at the top of the rotation, while Holmes gives Chicago another potentially important arm.
With Gausman, Holmes, Matthew Boyd and Shota Imanaga forming the core of the rotation, the Cubs suddenly have a much more intriguing pitching foundation. Edward Cabrera is also expected to return soon, while Javier Assad and David Peterson have provided valuable depth when needed.
That combination could become extremely important during the final weeks of the season.
The Cubs do not necessarily need to dominate every game. They simply need to consistently win series and take advantage of opportunities when Milwaukee stumbles.
The Brewers Series Could Decide Everything
The calendar provides Chicago with a potentially enormous opportunity.
On August 31, the Cubs begin a four-game series against Milwaukee. Soon afterward, they will meet the Brewers again for another three-game series.
That means seven games against the division leader could dramatically change the NL Central race.
Chicago should not expect to win all seven. That would be unrealistic.
The more reasonable objective is to arrive at those matchups within striking distance.
If the Cubs can erase even 2½ games from the current deficit before facing Milwaukee, they would put themselves in a position where those head-to-head games could have enormous consequences.
In other words, Chicago does not necessarily have to chase Milwaukee down immediately.
It simply has to keep the gap from becoming too large.
The Schedule Could Work in Chicago’s Favor
The Cubs have a valuable opportunity over the next several weeks.
After facing Kansas City, Chicago will take on the Nationals, Cardinals, White Sox and Mariners. Meanwhile, Milwaukee has challenging matchups against teams such as the Padres, Dodgers and Braves.
If Chicago continues winning while the Brewers finally experience some resistance, the division race could tighten considerably.
That is why the Cubs cannot afford to waste opportunities against teams they are expected to beat.
Every series matters now.
A sweep against Kansas City, for example, could provide exactly the kind of momentum Chicago needs before entering the more difficult portion of the schedule.
Chicago Has Already Paid the Price for This Push
The Cubs’ new expectations are also tied directly to what they surrendered at the trade deadline.
Chicago traded Ty Southisene and Brett Bateman to acquire Gausman. The organization then sent Jefferson Rojas to the New York Mets in the deal for Holmes and Tyrone Taylor.
Rojas was not just another prospect.
He entered the deadline period as the Cubs’ No. 2 prospect and was ranked among the top prospects in all of baseball.
Giving up that kind of young talent demonstrated how seriously Chicago views the current season.
The Cubs essentially decided that waiting for the future was no longer enough.
That decision deserves credit.
Prospects can become stars, but there is never a guarantee. At some point, a franchise has to determine when its window is open and make a serious attempt to capitalize.
Chicago has now made that choice.
But the New Additions Still Have Questions to Answer
Of course, trading for veterans does not automatically solve every problem.
Gausman entered the Cubs organization with a 5-10 record and a 4.38 ERA in 2026. At 35 years old, he is also approaching the end of his five-year, $110 million contract.
Those numbers do not immediately scream frontline ace.
But Chicago is betting on more than his current statistics.
Gausman has extensive postseason experience and has pitched in three consecutive postseasons. He also made five starts during Toronto’s run to the World Series last year.
That experience could prove valuable when the pressure intensifies.
Still, postseason experience will not matter if Gausman cannot consistently give Chicago quality innings.
The Cubs need the veteran right-hander to rediscover the form that made him such a valuable pitcher in the first place.
Holmes presents an entirely different uncertainty.
Before suffering a fractured fibula in May, he posted a 2.39 ERA across nine starts. However, he has been away from the major league mound for nearly three months.
Chicago is hoping it gets the version of Holmes that dominated early in the season rather than a pitcher who needs significant time to rediscover his rhythm.
That gamble could ultimately determine how successful the deadline strategy becomes.
Pete Crow-Armstrong Adds Another Reason for Optimism
While the pitching additions have received much of the attention, Pete Crow-Armstrong has emerged as another major reason Cubs fans should believe this team can make a run.
His defense has long been considered elite, but his offensive development has taken his overall value to another level.
Crow-Armstrong has increasingly looked like a legitimate National League MVP candidate, giving Chicago a young star capable of changing games with his bat, speed and defense.
His recent heroics have also become a major part of the Cubs’ late-season momentum.
In one recent comeback victory, Alex Bregman tied the game with a ninth-inning two-run homer before Crow-Armstrong eventually helped create the winning run by stealing third and forcing a throwing error.
Those are the types of plays that can define a postseason contender.
The Standard Has Changed
The Cubs can no longer hide behind potential.
For years, the organization could point toward prospects, future development and another offseason as reasons for optimism.
That argument has changed.
By acquiring Gausman and Holmes—and sacrificing significant prospect capital to do it—Chicago has effectively declared that 2026 is the season to take its shot.
That means reaching October should now be viewed as the starting point rather than the ultimate accomplishment.
The Cubs have enough talent to make the playoffs. They have enough pitching depth to compete with strong teams. They have a rising star in Crow-Armstrong and veterans capable of producing in big moments.
But the NL Central remains Milwaukee’s territory until someone takes it.
The Cubs are still 5½ games behind, and that gap will not disappear simply because Chicago is playing better baseball.
The opportunity, however, is sitting directly in front of them.
Seven games against Milwaukee could eventually determine whether the Cubs merely challenged for the division or actually took it.
For now, the mission is straightforward: keep winning, close the gap and arrive at the Brewers series with the NL Central within reach.
Chicago spent years building toward this moment.
Now, after finally pushing its chips into the middle of the table, the Cubs have to prove the gamble was worth it.
Leave a Reply