Insider Gives Bleak 2-Word Update on Orioles-Gunnar Henderson Contract Extension

The Baltimore Orioles did a fantastic job with their early picks in several MLB Drafts back when they were perennial bottom dwellers in the AL East.

They drafted catcher Adley Rutschman with the No. 1 overall pick of the 2019 MLB Draft, Gunnar Henderson one round later in that same draft, Heston Kjerstad with the No. 2 pick in the 2020 MLB Draft, and Jackson Holliday with the No. 1 pick of the 2022 MLB Draft.

While all three of these players probably haven't reached their full potential, there's a strong case to be made that three of them (Henderson, Rutschman, and Holliday) could still become superstars in the league. In fact, Gunnar Henderson already is a superstar, which was shown with him shining on the biggest stage at the 2026 World Baseball Classic.

United States shortstop Gunnar Henderson | Troy Taormina-Imagn Images

However, it's one thing to draft quality players and keep them for their ascent for the big leagues and the first few years of their respective MLB careers. It's another thing to re-sign them after their first contract and have them locked down for their primes.

And so far, Baltimore doesn't have Rutschman, Henderson, or Holliday signed long-term. They do deserve credit for agreeing to terms with top prospect Samuel Basallo, but the team would be wise to try to keep at least two of these key franchise pieces around for the foreseeable future.

Insider Gets Brutally Honest About Gunnar Henderson Contract Extension Talks

However, it doesn't seem like the extension talks with Henderson are going well at this point. This was made clear by a comment Jon Heyman of the New York Post made in a March 19 article, where he assessed where 12 MLB stars stand in potentially signing new contracts with their current teams.

Heyman noted that the Orioles made an extension offer to Henderson at this time last year. He then called it a "long shot" that a deal gets done before the 24-year-old hits free agency.

https://t.co/pbgFufZiMI Extension talk updates: Peralta/Mets not close yet, Kurtz offered about $130M (but deal seems unlikely now), Griffin, 19, offered biggest deal ever for no MLB service time, $100M-plus and that one might have a chance, maybe!
— Jon Heyman (@JonHeyman) March 20, 2026

There's still time for Baltimore to lock down Henderson, as he is still under team control through the 2028 season.

However, given that Scott Boras is Henderson's agent, who is notorious for preferring his players test the free agency landscape before sticking with a team, the chances that Orioles President of Baseball Operations Mike Elias can get Henderson to sign on the dotted line in the next couple of years might indeed be a long shot.

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