Orioles called a fit for Yankees star slugger in free agency

Could this surging New York Yankees outfielder end up with the Baltimore Orioles next season?

Aug 4, 2025; Arlington, Texas, USA; A view of a baseball bat and a New York Yankees bag and logo before the game between the Texas Rangers and the Yankees at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images | Jerome Miron-Imagn Images

Before the beginning of the 2025 MLB season, most experts and analysts believed the AL East division would be a three-team race between the Baltimore Orioles, the Boston Red Sox, and the New York Yankees, and that this would be one of the best divisions in MLB (as it typically is).

While the Yankees and Red Sox are both producing solid seasons, the Orioles have been the disappointing club out of this trio, as they have a 65-76 record heading into their September 6 game and are bottom-dwellers in the division. Instead, the Toronto Blue Jays (who were predicted to finish last by most) are leading the AL East right now.

Read more: Cal Ripken Jr. gives blunt assessment of Baltimore Orioles GM Mike Elias

While the Yankees are always expected to perform well, many anticipated their offense would show some regression this year compared to 2024, given that star slugger Juan Soto departed for their cross-town rival, the Mets, in free agency.

However, not only is Aaron Judge putting together another historic season and new acquisition Cody Bellinger is crushing the ball, but New York is getting a career-best campaign from 28-year-old outfielder Trent Grisham, which nobody had predicted.

Aug 24, 2025; Bronx, New York, USA; New York Yankees outfielder Trent Grisham (12) jogs from center field to the dugout after the sixth inning against the Boston Red Sox at Yankee Stadium. Mandatory Credit: John Jones-Imagn Images | John Jones-Imagn Images

Grisham is currently hitting .247 with an .837 OPS and 30 home runs in 2025. This is staggering, given that he hasn't produced better than a .675 OPS since the 2021 season.

Grisham is vastly exceeding the one-year, $5 million contract he signed with New York to avoid arbitration last winter. And given that he'll become an unrestricted free agent this upcoming offseason, he chose a great time to catch fire.

Orioles Predicted as One of Trent Grisham's Top Free Agency Destinations

New York Post MLB insider Jon Heyman published a September 5 article that ranked who he believes are the top 25 free agents this offseason, along with his predictions on the most likely suitors for each of these standouts.

Heyman ranked Grisham as the No. 21 free agent. And when noting his potential destinations, the Orioles were one of four teams (along with the Yankees, the Mets, and the Giants) included.

https://t.co/bcPSUqfGSL 25 top free agents, from Tucker to Alonso to Gleyber and more, and where they may land

— Jon Heyman (@JonHeyman) September 5, 2025

While the thought of adding Grisham is intriguing for Baltimore, they won't want to make a similar mistake to what happened with Tyler O'Neill last offseason. After O'Neill produced a career year for the Red Sox in 2024, the Orioles rewarded him with a three-year, $49.5 million deal in free agency.

This deal has not worked out so far, as O'Neill has been injured for much of this year. Perhaps this will serve as a lesson learned for Mike Elias and the rest of Baltimore's brass, which will keep them away from Grisham.

Or perhaps Grisham could be in Baltimore's starting lineup come 2026.