3 Things That Must Happen for the Cubs to Look Like a Postseason Threat Again

The month of May was one to forget for the Chicago Cubs. After a stellar start to the year, they went just 13-16 over those four weeks, stumbling down the NL Central standings in the process.

The good news is that it's a three-way race for the No. 2 spot in the division right now. Chicago is also only 5.5 games back of the Milwaukee Brewers, which is ground they could very well make up with a far easier schedule looming. The bad news, however, is that this unit is still looking like a shell of its early-season self.

So, how can that finally change? Let's go over three things that need to happen for the Cubs to get back on a winning track in June.

Dansby Swanson Needs to Be ... Average

Apr 23, 2026; Chicago, Illinois, USA; Chicago Cubs shortstop Dansby Swanson (7) hits a walk-off single against the Philadelphia Phillies during the tenth inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images | David Banks-Imagn Images

Dansby Swanson is always going to be at his best defensively ... and that's ok! He is a multi-time Gold Glove winner because of the magic he pulls off consistently at shortstop. The Cubs undoubtedly want that in the lineup.

At the same time, they do not want someone who is batting .183 over his first 57 games of the regular season playing an everyday role. Swanson has looked downright lost at the plate this year. At times, it's felt like pre-2020 baseball, when the Cubs would have their pitcher locked in at the bottom of the order. You basically go into every game knowing that the nine-hole isn't going to offer much.

In fairness to Swanson, he does carry an impressive 13.3 percent walk rate. This is bolstered by some early-season numbers, but he does remain pretty good at not chasing pitches. Still, when it comes to making solid contact, Swanson has only looked worse and worse. The infielder's barrel rate has plummeted to 7.7 percent, while his hard hit rate has dropped from 47.8 percent in 2025 to 42.7 percent this season, per Baseball Savant.

The Cubs as a whole have struggled with the breaking ball this season, but Swanson has been one of the main culprits. He's hitting just .113 on these pitches with a .196 wOBA. Teams are only going to continue to load up on sliders against him, which he's already seeing 21.6 percent of the time.

Look, can the Cubs' offense find a groove without Swanson heating up? Sure. He wasn't great during their win streaks either. However, it's never good to have someone in the lineup that an opposing pitcher feels this comfortable against. Especially when the offense as a whole is struggling, Swanson's repeatedly empty results are only put under a brighter spotlight. The sooner he can figure it out, the more well-rounded this Cubs lineup is going to look again.

Heck, he doesn't even have to become an on-base machine – just find some power again! Swanson's last home run came on May 18, and he has only four extra-base hits since May 1.

Jed Hoyer Needs to Pick Up the Phone

May 26, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs president of baseball operations Jed Hoyer observes batting practice before the Pittsburgh Pirates host the Cubs at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

Even if Matthew Boyd is trending in the right direction and Justin Steele could return after the All-Star break, the Cubs' pitching problems aren't going to be solved internally. Edward Cabrera hasn't lived up to the hype. Jameson Taillon has been serving up home runs on a silver platter. And Jordan Wicks has shown that he isn't prepared to contribute at the big league level.

Even if the Cubs' rotation begins to look more comfortable over the next couple of weeks, it's hard to take this group seriously as a playoff threat. The only way that is going to change is if Jed Hoyer can go out and find some reinforcements. But is he prepared to do that? Better yet, will he pay what it takes to get a deal done?

From Freddy Peralta to Joe Ryan to Tarik Skubal, there are expected to be several high-caliber starters available in the coming weeks. The Cubs find themselves in a somewhat advantageous spot, as they have a couple of pretty obvious trade chips. Kevin Alcantara is a top prospect who is seemingly ready for the kind of consistent MLB playing time that Chicago isn't ready to offer.

Matt Shaw is also a fascinating and rare trade chip. With one full season of big league experience under his belt, he has shown signs of being a genuinely impactful everyday starter. Nevertheless, the recent signing of Alex Bregman and the extension for Nico Hoerner have boxed Shaw out of an obvious role.

Might he be a serviceable corner outfielder in seasons to come, especially with Ian Happ and Seiya Suzuki headed toward free agency? Sure, but is that reason enough to keep him off the table for a potential ace? Probably not.

At the end of the day, even if the recent poor play is largely on the players, it's on Jed Hoyer to step in and help solve the problem. The best way he can do that is by bringing in an arm who can help limit early damage and take some of the burden off this offense.

Pete Crow-Armstrong Needs to Keep It Up

May 30, 2026; St. Louis, Missouri, USA; Chicago Cubs center fielder Pete Crow-Armstrong (4) catches a line drive from St. Louis Cardinals right fielder Jordan Walker (18) during the ninth inning at Busch Stadium. Mandatory Credit: Jeff Le-Imagn Images | Jeff Le-Imagn Images

Here comes PCA?

After reaching a new low point earlier this season after an ugly Crosstown Classic, Pete Crow-Armstrong has slowly but surely started to look more like his old self. The center fielder has a slash line of .297/.426/.541 with an OPS of .966 over his last ten outings. He has been one of the team's most consistent sources of offense, even recently having a four-hit day against the St. Louis Cardinals.

Speaking of which, this outing saw Crow-Armstrong smash a home run right to the fans who were calling him "overrated" before making a sliding catch for the final out. If Game 2 against the White Sox sounded the alarm bells, this 6-1 win over the Cardinals officially shut them off. As cliché as it may sound, Crow-Armstrong's swagger is a big part of what makes this Cubs team who they are. The more confident he is, the more confident this whole team could become.

With that in mind, Crow-Armstrong must stay on this recent track. He may only be 24 years old, but the Cubs need him to be a leader on and off the diamond, especially now that Craig Counsell moved him to the top of the order.

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