The Cubs are back in the postseason, but that doesn’t erase the hard truth hanging over the end of their regular season.
Chicago punched its ticket to the NL Wild Card round and will face the San Diego Padres, landing in the fifth seed after a season that was heavily shaped by injuries to Cade Horton, Justin Steele, and Ben Brown. Under those circumstances, getting into October is an achievement.
But the bigger question is whether that’s enough.
It wasn’t supposed to be. Back in February, Tom Ricketts set the bar plainly: win the NL Central and put the Cubs in the best possible position for the playoffs.
“We want to win the division. We should win the division.
We should be right there. You want to win the division for a lot of reasons not just because its aggravating not to - but you want to put yourself in the best position for the playoffs as well.”
By that standard, the season doesn’t pass muster. The Cubs did not win the division.
They were not right there. And they didn’t give themselves the best playoff position, finishing 14 games behind the Brewers.
That makes the uncomfortable reality impossible to dodge: injuries explain part of the journey, but they don’t change the verdict on the regular season. The Cubs made the playoffs despite the chaos, not because they hit the goal they set for themselves.
And the Brewers exposed the gap again. The source of that gap isn’t just bad luck. Milwaukee has become a machine, and Chicago’s answer has to be more aggressive than hoping a few smart bets pay off.
The Cubs did show some willingness to spend last offseason, signing Alex Bregman to a $175 million contract. That kind of move comes with expectation attached. It also points toward the kind of offseason the Cubs need now as they look to address pitching.
This is the area where comfort won’t cut it. The Cubs need to push beyond their usual limits in the market, because the low-risk approach can leave them stranded if the plan doesn’t work.
They already saw that dynamic play out with Edward Cabrera, Phil Maton, and Hunter Harvey. Chicago gave up its top organizational prospect for Cabrera, but his time with the Miami Marlins made him look like an unfinished product. The broader lesson is clear: if the Cubs want a different result, they’ll need to make different kinds of bets.
In Other News...
Cubs Get A Meaningful Playoff Boost Fans Did Not Expect
The Cubs are headed into a best-of-three Wild Card Series against the Padres with the kind of October backdrop that always sharpens the edges a little, and this one comes with a small but welcome comfort for longtime fans. Games will air on NBCSN and Peacock, and the broadcast booth will include a familiar name in Jim Deshaies, the Marquee Sports Network analyst who put off hip surgery so he could call the series.
For a club trying to turn a short postseason window into something bigger, having Deshaies on the call adds a layer of continuity at a time when everything else feels compressed and high-stakes. The schedule, start times and umpire assignments are all set, but Chicagos crowd will also have a voice attached to the games that has become part of the teams recent rhythm, even as the real drama waits to unfold on the field. [Read more 🡒]
Craig Counsell's Game 1 Pitching Choice Says Everything About This Series
Craig Counsell opened the Wild Card Series with a familiar hand, turning to Matthew Boyd to start Game 1 against the Padres. Boyd has been a trusted option for the Cubs in recent playoff stretches, and he has already taken the ball in a Game 1 matchup with San Diego before, a sign that Chicago is leaning into experience and comfort as the margin for error shrinks.
The Padres will counter with right-hander Michael King, while Counsell also confirmed Kevin Gausman will get into the series for the Cubs. In a short series, every pitching decision can shape the tone fast, and Boyds assignment suggests the Cubs are prioritizing a starter they know they can trust in a pressure spot while keeping the rest of the plan flexible. [Read more 🡒]
Padres Just Gave The Cubs A Wild-Card Twist To Worry About
The Cubs now have a little more to factor into their wild-card preparation after San Diego revealed its 26-man roster for the upcoming series. The Padres are carrying 15 position players and 11 pitchers, and the group includes some choices that signal how they plan to manage the matchup, including three catchers who could all be part of the mix over the series.
One of the biggest developments for Chicago is the return of Joe Musgrove, who had not pitched in the postseason since the 2024 wild-card round and sat out this season after Tommy John surgery. San Diego also made a few notable roster calls at the margins, bringing in Andujar and Sheets while leaving Sung-Mun Song, Wandy Peralta and Randy Vasquez off the list, another reminder that the Cubs will be facing a postseason opponent with some fresh pieces and a few familiar threats back in the fold. [Read more 🡒]