Orioles looking at contract extensions for two big names

Agent Scott Boras spoke to the media at the winter meetings Wednesday and was asked if the Orioles had reached out about extension talks with his clients Gunnar Henderson and Jackson Holliday. “Only once or twice a day,” Boras quipped, with Andy Kostka of The Baltimore Banner among those who passed his comments along. 

“Those kinds of things, obviously we listen, and Mike [Elias] and I talk a lot," Boras said. "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.”

Boras and his clients have a reputation of generally being averse to extensions, though that’s not to say they never happen. MLBTR’s Contract Tracker shows that Boras has negotiated extensions for clients such as Xander Bogaerts, Stephen Strasburg, Lance McCullers Jr. and more.

Both Henderson and Holliday are fairly inexperienced but extensions for players at this stage of their careers are becoming more common. Henderson has 184 games under his belt, but has thrived in those, winning American League Rookie of the Year here in 2023. Holliday has yet to make his Major League debut but is the consensus top prospect in the sport.

In recent years, players like Luis Robert Jr. and Eloy Jiménez have received notable extensions prior to even making it to the big leagues. Jackson Chourio, who currently falls just behind Holliday on those prospect lists, recently set a new benchmark for players with zero service time. He and the Brewers agreed to an eight-year, $82M extension with performance bonuses and a pair of club options. There have also been notable deals given to players with a small amount of major league experience, with each of Corbin Carroll, Wander Franco and Julio Rodríguez getting nine-figure guarantees.

For the Orioles, they would have to change strategy to get a deal done with either player. Since Mike Elias was hired as general manager in November of 2018, the largest guarantee they have given to anyone is the one-year, $13M deal they gave to Craig Kimbrel this week. The only extensions they have signed were two-year deals for John Means and Félix Bautista. In both cases, the player was rehabbing Tommy John surgery and was already under club control for the two seasons covered by the contract.

To be fair, the O’s have been aggressively rebuilding for much of the Elias tenure, so big spending wasn’t warranted. But they won 83 games in 2022 and still kept this modest last winter. The current offseason is still ramping up, so maybe there’s a bold move or two to come, but there’s been nothing too out-of-character just yet.

Due to that lack of spending, the club has the financial means to theoretically do anything it wants. The only commitments on the books for 2025 are $1M owed to Bautista and another $1M for the buyout on Kimbrel’s option. There’s nothing committed for 2026. Per the data of Cot’s Baseball Contracts, the O’s had a payroll as high as $164M in 2017, which put them in the top 10 league-wide. But much has changed since then.

Owner Peter Angelos collapsed in 2017 due to the failure of his aortic valve and his son John Angelos later was named “control person” for the club. Since then, the club has been rebuilding and keeping player costs to a minimum. Beyond that, they haven’t been able to agree to a new lease for their home ballpark, with the current agreement set to expire at the end of this month. It was reported earlier Thursday that David Rubenstein is attempting to purchase the club, though it’s unclear if he has a chance of succeeding or how long that would take.

There’s plenty of long-term uncertainty around the franchise so it’s an open question as to how much latitude Elias even has to commit future dollars to either of these players or any of the other on the roster. The aggressive tanking of a few years ago helped them load up their farm system, which has led to their current club being filled with talented youngsters like Adley Rutschman, Kyle Bradish, Grayson Rodriguez, Jordan Westburg and more. Getting one or more of those players to put pen to paper and stay in Baltimore for a long time would be a sensible strategy, but the likelihood of such a deal actually happening isn’t obvious at the moment.

In the short term, Elias will have to think about putting the best possible team on the field for 2024 and recently spoke to Rich Dubroff of Baltimore Baseball about that. They are set to have an outfield of Cedric Mullins, Austin Hays and Anthony Santander, though there are some different options for a fourth outfielder, with Elias naming Heston Kjerstad, Colton Cowser, Kyle Stowers and Ryan McKenna as suitors for such a gig.

Kjerstad had a solid showing last year, tearing through Double-A and Triple-A before getting into 13 Major League contests. The club probably wants to find him regular playing time somewhere, and he has played some first base before, but Elias shot down the notion of him moving there on a regular basis. “I don’t have designs on him becoming a full-time first baseman,” he said. “I think it’s something more that we’re trying to get it to a point where it’s in his back pocket and we can tap into it a couple of days a week.” The club has Ryan Mountcastle and Ryan O’Hearn as options for first base and designated hitter, so it’s not even a guarantee that there’s a cleaner path to playing time for Kjerstad there.

Despite all the crowding, the O’s have some openness to bringing in another outfielder, though it seems the odds of that happening are low. 

“I still see a ton of playing time and a lot of at-bats outside of our three primary outfielders. Right now, this is up for grabs. These guys, I don’t think any of them have really proven it yet over a long period of time in the majors, so we’re cognizant of that. If we can find external insurance or external help in this department, it’s not going to close the doors for those guys, and it wouldn’t be unwelcome from our end, either," Elias said. "Competition is good. Depth is good. These seasons are so unpredictable. Odds are you’ll get some injuries, so we have to prepare for all that. We’ll talk to free agents that might be a fit for joining our outfield mix, but we have high hopes for the names that I mentioned.”