The Cubs and Padres may be done meeting in October for now, but that doesn’t mean the competition between them is over.
For the second straight year, Chicago and San Diego met in the NL Wild Card Round, and the home team won each time. This time around, it was the Cubs whose season ended in frustration, a result that felt especially bitter after what was described as an all-time year from Pete Crow-Armstrong.
Once again, the problem came back to the same place that has haunted Chicago in recent Octobers: pitching that didn’t hold up when it mattered most. In 2025, it was a bullpen game in a must-win NLDS Game 5 in Milwaukee. This year, it was turning to a less-than-100 percent Kevin Gausman with the season on the line after Matthew Boyd had been out-classed in the opener.
That October pain could easily spill into the winter.
Both clubs are expected to make pitching a major priority in free agency, and they could wind up chasing some of the same arms. The biggest name in that group, outside of Tarik Skubal, is Michael King.
He has become the top free-agent starter in this class, and with good reason. Over the last three seasons with San Diego, King has posted a 3.15 ERA across more than 430 innings, and he is set up to cash in as he heads into his age-32 season after opting out of the final two years of his deal.
King would instantly qualify as the biggest-name starter the Cubs have pursued in years, but the road to signing him won’t be simple. He is said to be very interested in returning to San Diego, which gives the Padres a real edge if they want to keep him.
Chicago could also take a run at another Padres arm in Adrian Morejon. The left-hander has been one of San Diego’s most trusted relief weapons, and he’s now headed for free agency too. He backed that reputation this season by striking out 107 batters in only 86 regular-season innings, making him exactly the kind of late-game force the Cubs have lacked.
The Cubs’ bullpen needs more than a patch job, and Morejon fits the profile of a pitcher who could help change that. Casey Mize, who joined San Diego at the deadline, is mentioned as a more realistic Chicago target, but the idea is clear: half-measures won’t be enough for Jed Hoyer and the front office.
And this isn’t just about one or two players. The larger picture is that both teams sit near the top of the National League and share plenty of the same roster needs entering what could be an unusual offseason, with a lockout looming in December. There may even be another Cubs-Padres October matchup waiting next fall.
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