Matt Shaw's Best Opportunity With Cubs Will Likely Come In October

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Every year, there are certain players that just seem to come alive in the postseason. Last year, we saw guys like Trey Yesavage and Ernie Clement play meaningful roles for the Toronto Blue Jays despite not necessarily lighting up the regular season (the former had spent nearly the entire year in Triple-A). Yet both became important pieces during Toronto’s postseason run, helping the team come within one win of a World Series title. Odds are good there will be multiple players who fit that description in 2026. And I think Matt Shaw has the potential to be one of them for the Chicago Cubs.

When he’s been on the field, it’s been a promising year for Shaw. He’s made some notable offensive improvements, raising his OPS from .690 last season to .751 this year while also walking more, striking out less, and showing slightly more power.

The Cubs are very likely going to be a Wild Card team this year. That means they're likely going to have to navigate the Wild Card round, and based on the current standings, they could find themselves facing one of the Phillies, Diamondbacks or Braves. Interestingly enough, all three of those potential matchups could line up quite well for Shaw.

He hasn’t been an everyday player for the Cubs this season; instead, he’s settled into more of a short-side platoon role against left-handed pitching while also serving as a pinch-hitter late in games. It hasn’t been the most prominent role on Chicago’s roster, but the postseason could give him a chance to make a much bigger impact.

The starting rotations the Cubs could see in October feature a lot of talented left-handed pitchers. Take the Phillies, for example. In a potential three-game Wild Card series, Cristopher Sánchez and Jesús Luzardo would both be lined up to start. Both left-handers have plenty of swing-and-miss ability, and with Shaw’s improving bat-to-ball skills, he feels like someone who could find himself in the lineup against either (or both) of them. He doesn’t necessarily need to turn into a completely different hitter overnight. If he can continue making contact, limiting strikeouts and taking advantage of favorable matchups, he could become a valuable piece against some of the best left-handed pitching in the National League.

The same goes for the Braves and Diamondbacks. Atlanta’s rotation is headlined by Chris Sale, while Arizona has Eduardo Rodríguez. Both are left-handed starters, and both would present situations where I’d expect Shaw to be in the lineup.

Then, there’s the possibility of advancing beyond the Wild Card round. If the Cubs make it to the NLDS or NLCS, they could potentially run into teams like the Dodgers or Brewers. And even in those matchups, there are left-handed pitchers who could give Shaw an opportunity. Guys like Tarik Skubal, Blake Snell, and Kyle Harrison are all examples of left-handed arms this team could potentially see during a postseason run. If one of those guys is on the mound, I’d have Shaw in the lineup.

Of course, he doesn’t necessarily have to start to make an impact. One of the most valuable things about the postseason is that a player can completely change the course of a game with one at-bat. A clutch pinch-hit late in a close game could be the difference between moving on and going home, and the Cubs don’t have to look very far for an example of that. Just ask Miguel Montero.

Montero famously delivered a pinch-hit grand slam against the Dodgers in Game 1 of the 2016 NLCS, helping the Cubs take a series lead before eventually winning their first World Series in more than a century. That’s the type of moment that can turn a player into a postseason hero. And while it would be unfair to expect Shaw to have a moment of that magnitude, his skill set and defensive versatility could give him an opportunity to make a contribution off the bench.

He won’t be asked to carry the Cubs’ offense, nor will he need to suddenly become a massive power hitter. He simply needs to take advantage of the opportunities that come his way. And if Chicago runs into a string of left-handed starters throughout October, those opportunities could come pretty frequently.