As the calendar flips to September and the regular season winds down, the Chicago Cubs find themselves in promising territory-20 games over .500 and barreling toward what looks like their first postseason berth since 2020. It’s been a year of resurgence on the North Side, fueled by a deep roster and a mix of savvy veteran leadership and emerging young talent.

But with October baseball comes a new challenge: trimming the expanded 28-man roster back down to 26 for the postseason. That means some tough conversations are on the horizon.

While the Cubs have leaned on depth to get to this point, the postseason demands precision-every roster spot has to serve a purpose. And that could leave a few familiar names on the outside looking in.

Let’s take a closer look at three players who, based on current trends and team needs, may not make the cut when the Cubs set their playoff roster.

Justin Turner, 1B/3B

When the Cubs inked Justin Turner to a one-year deal last winter, the hope was that he’d bring a veteran presence with a bat that could still deliver in key moments. Unfortunately, the production just hasn’t followed. Turner’s .215/.284/.315 slash line speaks to a season where he’s struggled to find consistency at the plate.

He’s shown some flashes against left-handed pitching-hitting .273 with a .753 OPS and three home runs-but those moments have been few and far between. Since the trade deadline, Turner has logged just 21 at-bats, a clear indication that his role has diminished significantly.

What really complicates his postseason chances is the addition of Carlos Santana. The veteran switch-hitter has taken over the 1B/DH role that Turner might have filled, and his ability to hit from both sides of the plate gives the Cubs more flexibility. As much as Turner’s leadership and experience are valued in the clubhouse, it’s hard to justify a postseason roster spot for a player who’s become more of a bench piece than an everyday contributor.

Jameson Taillon, SP

Taillon’s situation is a little different-it’s not so much about performance as it is about roster math. With the Cubs likely to carry five starters into October-Matthew Boyd, Cade Horton, Shota Imanaga, Colin Rea, and Mike Soroka-there’s only so much room to go around. And when you factor in the need for a deep, versatile bullpen, the numbers just don’t work in Taillon’s favor.

He’s had an up-and-down season, marked by inconsistency and injury, and while his postseason experience is a plus, the Cubs seem to have more reliable options right now. If he does return from injury in September, it might be too little, too late to change the front office’s mind.

Postseason rosters are about current form, not past reputation, and unless something changes drastically in the final weeks of the season, Taillon could find himself on the outside looking in when the roster is finalized.

Reese McGuire, C

On the surface, keeping Reese McGuire around when Miguel Amaya returned from injury seemed to signal that the Cubs might consider carrying three catchers into October. But that idea may be more theoretical than practical, especially with roster spots at a premium.

The real curveball came with the Cubs’ under-the-radar signing of Billy Hamilton to a minor league deal-just in time to make him postseason-eligible. Hamilton’s speed is his calling card, and in a playoff series where one stolen base can change a game, his presence on the bench could be a strategic weapon. Think of him as a modern-day Terrance Gore, who famously made a one-game cameo in the 2018 postseason just to run.

If Hamilton is added for his baserunning prowess, the Cubs will need to trim somewhere else-and carrying three catchers doesn’t make much sense if only two are expected to get meaningful playing time. That likely leaves McGuire as the odd man out, with Amaya and the team’s Opening Day catcher holding down the fort behind the plate.

Final Thoughts

The Cubs are in a good place-poised for a postseason run and armed with one of the deeper rosters in the National League. But October baseball is a different beast.

It’s about matchups, momentum, and maximizing every roster spot. That’s why some tough decisions are coming, and why players like Turner, Taillon, and McGuire might not be part of the journey when the lights shine brightest.

Roster decisions are rarely easy, especially for a team with real October aspirations. But that’s the price of contention-every move matters, every role is magnified, and only the most adaptable survive. The Cubs are about to find out if they’ve built a roster ready for that pressure.