Padres, Cubs could find themselves going head-to-head in free agency after playoffs showdown

Each of the last two years have featured the Chicago Cubs and San Diego Padres squaring off in the NL Wild Card Round, with the home team emerging victorious each time. This year, that meant the Cubs' season ended early in what amounts to a wasted all-time season from Pete Crow-Armstrong.

In frustrating fashion, it was the same weakness that proved Chicago's undoing in each of the last two Octobers: impactful pitching. In 2025, that meant a bullpen game in a must-win NLDS Game 5 in Milwaukee and, this year, it meant rolling out a less-than-100 percent Kevin Gausman with the season on the line after Matthew Boyd was out-classed in the opener.

But if you think the offseason means the end of this head-to-head, think again. Both San Diego and Chicago will have a major focus on pitching this winter, and are poised to battle it out with one another to land some of the market's most coveted arms.

Apart from Tarik Skubal, who's in a class unto himself, King is widely viewed as the top free-agent starter in this winter's class. He's been rock-solid for the Padres over the last three years, posting a 3.15 ERA in over 430 innings of work and will surely cash in heading into his age-32 season after he opts out of the remaining two years on his deal.

Michael King, Adrian Morejon could both be Cubs' free agent targets

King would be the highest-profile starter the Cubs have had in years, but the right-hander is very interested in returning to the Padres, so it may be an uphill battle for Jed Hoyer and the front office. Another prime arm that would be a major change-of-pace for Chicago is lefty Adrian Morejon, the longtime Padres' relief ace who is ticketed for free agency, as well.

He's going to be a hot commodity this winter - as he should be. Morejon punched out 107 batters in just 86 regular-season frames, and we all know the Cubs' bullpen desperately needs a legitimate weapon to lock things down in the ninth. Casey Mize, who came to San Diego at the deadline, feels like a more reasonable Cubs target, but half-measures aren't going to get the job done, so he certainly can't be Hoyer's top addition.

Obviously, there are names new to both organizations that could have some crossover: the overarching story here is we're talking about two top NL teams with a lot of similar needs as we near what will be a highly irregular offseason, thanks to the looming lockout in December. And, who knows, maybe we'll get a third-straight October showdown between them next fall.

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