Update: Orioles Approached Scott Boras About Extensions for Young Stars Two Years Ago

The Baltimore Orioles had interest in extending at least two of their young stars two year ago, both of whom are represented by the same agent.

Feb 27, 2025; Sarasota, Florida, USA;  Baltimore Orioles shortstop Gunnar Henderson (2) at bat during the first inning and then left the game during the inning against the Toronto Blue Jaysat Ed Smith Stadium.

Lately, Major League Baseball has been caught in a tidal wave of contract extensions for up-and-coming stars.

Two signed long-term deals this week. San Diego Padres star Jackson Merrill agreed to a $135 million contract over nine years.

Boston Red Sox rookie Kristian Campbell agreed to an eight-year deal worth $60 million.

The deals are designed to pay those players well above what they would get during their six years of team control, which includes three years of base salary, followed by three years of arbitration.

It also represents a level of security for the team as it can control costs.

The Baltimore Orioles would be seen as a leading candidate to take advantage of this process, given the cadre of young stars they have — Gunnar Henderson, Adley Rutschman, Jordan Westburg, Colton Cowser and Jackson Holliday.

In a wide-ranging piece in the Baltimore Banner, three different agents talked about how and why these deals get made — or not made. Foremost among those agents was Scott Boras, who represents at least three of Baltimore’s young stars.

Boras was interviewed and he noted that the Orioles have tried to engage with two of his clients — Gunnar Henderson and Jackson Holliday — about long-term extensions.

“Those kinds of things, obviously we listen, and (O’s general manager) Mike (Elias) and I talk a lot,” Boras continued. “Obviously, our job is to filter those phone calls and relay them to the player, and kind of discuss it and see if it’s something that the player himself is interested in.”

The interest in an extension in 2023 for Henderson would have come during his American League rookie of the year campaign, as he slashed .255/.325/.489 with 28 home runs and 82 RBI.

He was also named a Silver Slugger and finished eighth in AL most valuable player voting.

Following that, Henderson finished fourth in AL MVP voting and was an All-Star last year after a career season in which he slashed .281/.364/.529 with 37 home runs and 92 RBI.

The discussion on Holliday would have been interesting because at that point Holliday was still in the minor leagues. He was the game’s No. 1 prospect, and he didn’t make his MLB debut until last season.

A deal like that probably would have resembled similar deals for players like Milwaukee’s Jackson Chourio or Detroit’s Colt Keith, both of whom signed long-term deals before playing an MLB game.

Both Holliday and Henderson are still pre-arbitration players, though Henderson will go through the process for the first time this offseason.

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