Chicago Cubs need to target these free agent San Diego Padres

The Chicago Cubs turned in a miserable collective performance in the Wild Card series against the San Diego Padres and, as a result, were eliminated in two games. Unfortunately, given the pitching woes of this year’s team, the disappointing end to the season wasn’t exactly unexpected.

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Cubs president Jed Hoyer, in the two-game postseason look at the Padres, should’ve seen plenty to add to his shopping list this offseason as he stares down the reality of having to practically rebuild an entire pitching staff.

In baseball, the sour-note equivalent of “if you can’t beat them, join them” is “if you can’t beat them, sign away their talent.”

So, with that in mind, here’s a look at some pending free agent Padres talent the Cubs definitely should look at snatching up.

Morejon and King should be primary Cubs targets

Adrian Morejon, Chicago Cubs, San Diego Padres — Sep 30, 2026; San Diego, California, USA; San Diego Padres pitcher Adrian Morejon (50) reacts in the end of the eighth inning against the Chicago Cubs during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images

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Adrian Morejon came into Game Two of the Wild Card series and blew the Cubs away, delivering the kind of dominant late-inning relief appearance Chicago has rarely gotten from their own bullpen this season.

The Cubs desperately need a reliable and overpowering late-inning presence and they must get over their reluctance to invest in elite-level relief talent. The 27-year-old has posted a 2.58 ERA over his last three seasons with 248 strikeouts in 223.1 innings. He’s stuck behind Mason Miller in San Diego, but would be a closer almost anywhere else in baseball and should be chomping at the bit to get that opportunity. Estimates place his going price at about $60 million over four years. If the Cubs are serious about postseason life, they’ll spend the money

The Cubs were linked to Michael King this past offseason, but couldn’t/wouldn’t pull the trigger on signing him. Instead, King re-signed with the Padres for a three-year, $25 million deal that gives him opt-out options after this 2026 season and the next. King is expected to opt-out and explore a longer deal for more money and the Cubs should absolutely be looking to scoop him up—especially after seeing the way he absolutely nullified their offense in a dominant Game One start in the Wild Card series.

The rest of the shopping list

Robbie Ray, Chicago Cubs, San Diego Padres — Sep 16, 2026; Denver, Colorado, USA; San Diego Padres pitcher Robbie Ray (38) pitches in the first inning against the Colorado Rockies at Coors Field. Mandatory Credit: Christopher Hanewinckel-Imagn Images

Starting pitcher Robbie Ray came to the Padres at the trade deadline from the San Francisco Giants, where he was having a career year. He didn’t pitch all that well for the Padres down the stretch, but his worth as a left-handed starting pitcher with a long history of success will see him get lots of attention when he hits the free agent market this offseason. He’s 35, so that may damper some of the enthusiasm in pursuing him, but the Cubs will need established performers heading into a 2027 season where, possibly, their entire end-of-season starting rotation (Boyd, Imanaga, Gausman, Holmes, Peterson) could be gone via free agency.

Casey Mize was a wild disappointment for the Padres after being acquired from the Detroit Tigers at the trade deadline. But up until his injury-hampered run in San Diego, the 29-year-old right-hander was a lights-out rotation piece, posting a 2.70 ERA through 16 starts for the Tigers. Again, the Cubs desperately need rotation help and some puzzle pieces with a proven history of success.

If the Cubs are looking for the bullpen success they failed to achieve with the signings of Phil Maton, Hoby Milner, and Hunter Harvey last offseason, they would do well to pursue right-handed setup man Jason Adam. The right-hander has been the picture of consistent bullpen excellence since his 2020-2021 run with the Cubs, delivering ERAs under 3.00—and sometimes under 2.00—in the five seasons after that. An Adam-Morejon one-two late-inning punch would be a significant improvement over the current Jacob Webb-Daniel Palencia late-inning combo.

It should be obvious at this point that all of the Cubs’ free agent targets must be pitching. They will also, of course, have to figure out a way to fill at least one of their corner outfield spots and catcher. But the priority this offseason has to be pitching or 2027 will look uglier than the end of 2026.

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