14 former Cubs who could make Chicago take notice during the 2026 MLB playoffs

We're a little more than a week from the 2026 MLB playoffs getting underway. Wild card action gets underway on Tuesday, Sept. 29 and, assuming the Chicago Cubs handle business in the regular season's closing chapter, they'll be a part of that fray.

But as we wait to see if Chicago punches a postseason ticket for the second time in as many years behind presumptive National League MVP Pete Crow-Armstrong, let's take a quick look around the league at some former Cubs we will see in the playoffs (and a few whose teams are fighting for their October lives to finish the year).

Former Cubs superstars are littered across this year's MLB playoffs field

This group certainly doesn't lack star power. Let's start with the man leading the Philadelphia Phillies, who could be the Cubs' first-round matchup in the wild-card round: Kyle Schwarber. One of the game's elite power bats, Schwarber has done what he always does again in 2026. He and Crow-Armstrong are locked in a race to lead the league in homers and Schwarber is closing in on 400 long-balls in his career. This a guy built to beat you in October.

The AL Wild Card Series could be MLB's dream scenario: Yankees-Red Sox - a matchup that has a ton of former Cubs, including Cody Bellinger in New York and former teammates Aroldis Chapman and Willson Contreras reunited in Boston. Emotions would be high in this one and Boston just got Contreras back off the IL. Anything can happen when these two meet, especially in the playoffs.

There's a clear team to beat in the back-to-back reigning champion Los Angeles Dodgers and their $60 million a year disaster, Kyle Tucker. He's been worse than anyone could have envisioned, but he's slugging north of .500 in September, and you can bet Dodgers fans would forgive all if he came up clutch with some playoff homers that propelled them to a three-peat.

I'd be remiss if I didn't put Dylan Cease on this list. No, he never pitched at the big-league level for the Cubs, but he'll always be remembered as a piece of the infamous Jose Quintana trade that also sent Eloy Jimenez to the South Side. Cease will be an AL Cy Young finalist this year and if Toronto can sneak in, we'll see him in some big spots - as well as rookie Brett Bateman.

Bateman was traded to the Blue Jays in the Kevin Gausman deal this summer and has amassed 2.0 bWAR in just three dozen games. Whether they get in or not, he's been a tremendous story for Toronto down the stretch.

I hate to even mention him, but former Cubs reliever-turned-Milwaukee Brewers closer Trevor Megill will be waiting to lock down games for the NL Central champs in the playoffs. The hard-throwing right-hander is part of a formidable Milwaukee relief corps that was built for October.

Role players and supporting cast who played for the Cubs are ready to go

Joc Pederson and the Texas Rangers are among the teams looking to sneak into the playoffs at the last minute, but the former Cubs outfielder has had a nice bounceback year. He's eclipsed 25 home runs for the first time since 2019 with the Dodgers, so he's more than capable of popping a big fly in October.

Nick Madrigal has landed on his feet with the AL East champion Tampa Bay Rays, while left-hander Sean Newcomb and the White Sox are desperately looking to fend off a September collapse. Old (multi-time) friend Nicky Lopez and Trevor Williams are in Arlington with Pederson but, like I said, their future is yet to be determined.

Last, but not least, Michael Soroka and the Arizona Diamondbacks are trying to find a way into the NL playoff picture. Cubs fans won't soon forget his name after Jed Hoyer traded for him last summer in a bid to bolster the pitching staff only for him to leave his first start after two innings, then spending much of the rest of the year on the shelf. Good times.

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