The Cubs may need to shop for outfield help this winter, and one of the more intriguing names on the market is a familiar one from the Bronx.
With Seiya Suzuki and Ian Happ both potentially headed for free agency, Chicago could find itself staring at a pair of holes in the corners. Pete Crow-Armstrong is already locked in as the center fielder, but that still leaves room for another bat and another glove, whether in left, right or in a fourth-outfielder role.
That’s where Trent Grisham enters the picture.
The former Yankees center fielder is coming off a season that didn’t look great on the surface, but there’s enough underneath to make him a real fit for the Cubs. Chicago already showed last winter that it can squeeze value out of a bounce-back candidate, and Michael Conforto was the proof. In 113 games, Conforto hit .240/.331/.469 with an .800 OPS, 15 homers, 45 RBI and 0.7 bWAR after the Cubs grabbed him on a one-year, $2 million deal following a rough year with the Los Angeles Dodgers.
Grisham could be the next version of that kind of move.
His 2026 line with the Yankees was .211/.308/.395 with a .703 OPS, but he still managed 18 home runs. The expected numbers paint a more encouraging picture, too: a .245 expected batting average and a .429 expected slugging percentage. He also showed some real discipline at the plate, ranking in the 78th percentile in hard hit rate and average exit velocity, the 99th percentile in chase rate, the 83rd percentile in swing-and-miss rate and the 88th percentile in walk rate at 12.6 percent.
Health is part of the equation here. Grisham spent two separate stretches on the injured list with a right hamstring strain, and a cleaner season could put him closer to the production he posted in 2025, when he slugged 34 homers, drove in 74 RBI, finished with an .812 OPS and produced 3.5 bWAR.
The defensive side is a little less tidy. Grisham has posted -8 Outs Above Average in center over the last two seasons, though he was regarded as an elite defender with the San Diego Padres and during his first year with the Yankees in 2024.
At 30 years old, and with a left-handed bat, Grisham fits the profile of a short-term, low-risk gamble. If the Cubs believe there’s still another offensive jump in there - and enough defense to keep him useful in the outfield - he could become their next success story.
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Imanagas departure would leave another notable hole for a staff that needs more than just a tweak. Chicago is unlikely to make re-signing him the top priority, which puts the spotlight squarely on how aggressively the Cubs will shop for arms and how quickly they can add them. The rotation rebuild was always going to matter, but losing a pitcher of Imanagas caliber would make the task feel even more urgent. [Read more 🡒]
Cubs Now Face An Ian Happ Exit That Could Get Uncomfortable
The Cubs have opened the door to a tricky winter by declining to give Ian Happ a qualifying offer, a move that sends the veteran outfielder into free agency without draft-pick compensation attached. It is a notable shift for a player who has been a familiar part of the lineup and clubhouse, and it immediately puts Chicago in a more uncertain spot as it weighs how to replace his production and presence.
Ian Happs market could still develop quickly, especially with the Seattle Mariners and Cincinnati Reds reportedly showing interest, both teams carrying ties to former Cubs personnel now in their front offices. Happs recent struggles may temper the bidding, but the broader free-agent crop does him a favor because there are not many established hitters available, which could make him a more appealing option than the raw numbers might suggest. [Read more 🡒]