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Cubs could turn a Yankees castoff into their next outfield success story

The Cubs could target this ex-Yankees outfielder in the offseason.
ByPat Ragazzo
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Oct 7, 2026; Bronx, New York, USA; New York Yankees outfielder Trent Grisham (12) reacts after striking out during the seventh inning against the Tampa Bay Rays in game three of the ALDS for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Wendell Cruz-Imagn Images
Oct 7, 2026; Bronx, New York, USA; New York Yankees outfielder Trent Grisham (12) reacts after striking out during the seventh inning against the Tampa Bay Rays in game three of the ALDS for the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Wendell Cruz-Imagn Images | IMAGN IMAGES via Reuters Connect

The Chicago Cubs could lose both of their starting corner outfielders in free agency this offseason in right fielder Seiya Suzuki (qualifying offer) and left fielder Ian Happ. As a result, they will likely need to bring in some outfield help this winter.

One name that's available on the open market, who performed well at times in a big market is ex-New York Yankees center fielder Trent Grisham. The Cubs already have a center fielder in NL MVP winner Pete Crow-Armstrong, but they could possibly bring in Grisham to play left, right or serve as their fourth outfielder.

Cubs could turn Trent Grisham into their next outfield success story

The Cubs had good luck with rejuvenating Michael Conforto's career in 2026. Conforto slashed .240/.331/.469 with a .800 OPS, 15 home runs, 45 RBI and a 0.7 bWAR in 113 games last season. That's more than solid production for a backup outfielder. The Cubs got Conforto for one-year, $2 million and he rewarded them by bouncing back after an abysmal campaign with the Los Angeles Dodgers.

So, could Grisham be the Cubs' next version of Conforto? It's certainly possible when you look at his underlying metrics last year and overall track record.

According to Grisham's Baseball Savant page, he was in the 78th percentile in hard hit rate and average exit velocity. He also doesn't chase pitches out of the zone (99th percentile) or swing-and-miss much (83rd percentile). Grisham's 12.6 percent walk rate was in the 88th percentile in baseball as well.

Although Grisham slashed .211/.308/.395 with a .703 OPS, he did crack 18 homers for the Yankees. Not to mention, his expected batting average was a much better .245 and his expected slugging percentage was .429.

He also spent two separate stints on the IL with a right hamstring strain, so in a healthier season he could potentially produce closer to the numbers he put up in 2025, where he slugged 34 homers, drove in 74 RBI, had an .812 OPS and a 3.5 bWAR.

Grisham has struggled defensively across the past two seasons with -8 Outs Above Average in center. However, he was known as an elite defender during his time with the San Diego Padres and first season with the Yankees in 2024.

If the Cubs can get some type of version of the Grisham who was an offensive force two seasons ago and that can play at least average defense in the outfield, it would make sense to bring in the veteran on a short-term deal to prove himself in 2027.

Grisham turned 30-years-old earlier in the month, and his lefty bat could be a fine addition to the Cubs' lineup on a low-risk, high-reward type of contract. He could just be the Cubs' next success story in the outfield if they take a chance on him.

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