Ken Rosenthal's latest Orioles extension prediction totally misses the mark

The Baltimore Orioles' decision to hand out an 8-year extension to Samuel Basallo has left many Orioles fans wondering who the next player is that will be locked up to a long-term deal, and the obvious candidate is Gunnar Henderson. Ken Rosenthal, however, floated Jackson Holliday as another extension candidate, and it feels like the baseball insider hasn't been following the season Holliday is having.

"You're gonna have difficulties with Gunnar Henderson and Jackson Holliday. Both are represented by Scott Boras. Both are more inclined, perhaps, to go to free agency than other players would, because Scott prefers his guys to establish their values on the open market," Rosenthal outlined.

First and foremost, it feels like a rush to judgment to suggest Holliday as an extension candidate. There certainly was a point, during Holiday's ascent through the Orioles' system as one of the best prospects in the game, that he was considered to be at the center of the next Orioles' contending team, but his initial run has proved that may not be the case.

2025 has been Jackson's first full season at the Major League level, and it's been plagued with inconsistency. There have been times when Holliday appeared to be breaking out this season, pushing for an All-Star appearance during the first half, but the 21-year-old infielder has yet to take that next step forward. Holliday has been a below-average offensive player since his hot start, and that has led to some reconsideration about his value to the team moving forward.

MLB insider’s Orioles-Jackson Holliday extension prediction feels like a total reach

Until Holliday can bring any form of consistency to his offensive profile, it wouldn't make sense for the Orioles to be eager to sign him to an extension. Similarly, if your Holliday, signing an extension now feels like leaving money on the table, since the premise would be the Orioles buying value before his value potentially soars.

The caveat to all of this is that Holliday is still very young, and the potential remains that he could turn into a superstar. That would be when the Orioles can be ready to have a conversation, but that's not a point they are at right now.

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