The link is puzzling, as Chicago’s outfield appears set with top prospect Owen Caissie, and Grisham now has a $22M qualifying offer attached, which would cost the Cubs a draft pick.
CHICAGO — The overwhelming expectation is that the Chicago Cubs will not be a serious bidder for Kyle Tucker this offseason, which leads to the larger question of how the team will replace his production in the starting lineup.
The immediate answer will likely be top prospect Owen Caissie, but it would be a mistake for the Cubs to go into 2026 without some veteran insurance.
This premise appears to be at the center of a new report from Bleacher Report’s Kerry Miller, who listed the Cubs as a “potential suitor” for free-agent outfielder Trent Grisham. The link, however, is being called “head-scratching” by analysts.
Grisham’s “Curious” Free Agent Case
Grisham, 29, will be a fascinating case to follow this offseason. His 2025 season with the New York Yankees was easily the best of his career. In 143 games, he slashed .235/.348/.464 with 34 home runs and a 129 wRC+.
This was a massive breakout, as it was the only season in his career where he hit over 20 home runs or registered a wRC+ over 100 while playing 100+ games.
This performance prompted the Yankees to make a “semi-surprising” move, officially extending him the $22.025 million qualifying offer on Thursday. This now means that any team (including the Cubs) that signs Grisham would also have to forfeit a draft pick.
A Full Outfield at Wrigley
Regardless of Grisham’s breakout, it’s “hard to connect” him to the Cubs. The team’s 2026 outfield and designated hitter alignment already appears to be set:
- Right Field: Owen Caissie
- Center Field: Pete Crow-Armstrong (2025 Gold Glove winner)
- Left Field: Ian Happ (4-time Gold Glove winner)
- Designated Hitter: Seiya Suzuki
- Bench (C/1B/DH): Moises Ballesteros
There does not appear to be a clear path toward the regular plate appearances Grisham would command. While he may be a fallback option for teams that miss out on top-tier free agents like Tucker or Kyle Schwarber, the link to the Cubs is confusing.
Circumstances could change, and if the Cubs move one of their established outfielders in a trade, it would become easier to suggest Grisham as a fit. As of now, though, the move doesn’t appear likely.
