What a Jackson Holliday extension could look like for the Orioles

Baltimore could look to buy low on the young infielder with a long-term extension this offseason.

Sep 6, 2025; Baltimore, Maryland, USA; Baltimore Orioles second baseman Jackson Holliday (7) celebrates after hitting a home run during the ninth inning against the Los Angeles Dodgers at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | Daniel Kucin Jr.-Imagn Images

With the manager hunt out of the way, the Baltimore Orioles can now divert their full attention to preparing their roster for Opening Day 2026.

After missing the playoffs with a disappointing 75-87 record, there will likely be some reinforcements added this winter by way of trade and free agency. That said, the Orioles have built a core of promising young talent that isn't likely to change for years to come.

With everyone back and healthy, the O's lineup will center around 25-year-olds Jeremiah Jackson and Colton Cowser, 24-year-olds Gunnar Henderson and Dylan Beavers, and 21-year-olds Samuel Basallo and Jackson Holliday.

Henderson saw a dip in production after an intercostal strain zapped his power from 37 home runs in 2024 to just 17 in 2025. Still, the former second-round pick led all Orioles position players with 4.8 fWAR last year and has proven to be one of the league's most valuable all-around shortstops.

Injuries aside, Baltimore's main concern with Henderson going forward is what he will end up costing throughout his three years of arbitration before hitting free agency. Despite reported attempts to lock the young star up to a long-term contract before the 2025 season, Mike Elias and company could not get a deal done and will now pay Henderson a projected arbitration salary of $6.6 million in 2026. Barring a surprising extension, he will become a free agent in 2029, when he could command somewhere around $500 million on the open market.

Here are the Orioles’ projected arbitration salaries, per MLB Trade Rumors.

The most notable ones:

Ryan Mountcastle (Arb-3) — $7.8M
Gunnar Henderson (Arb-1): $6.6M
Félix Bautista (Arb-2) — $2.1M pic.twitter.com/LsRJwkxpMz

— Jacob Calvin Meyer (@jcalvinmeyer) October 6, 2025

But the newly appointed president of baseball operations could use the upcoming offseason as an opportunity to rewrite Baltimore's poor history of extending their drafted talent. In August, Baltimore signed Basallo to an eight-year, $67 million contract extension after just four big league games, making him the highest-paid pre-arbitration catcher in MLB history.

Read More: Baltimore Orioles sign young catcher to long-term extension

Basallo's extension was the first long-term contract handed out by Elias since he took over as general manager in November 2018, making them the last team in MLB to do so during that period. But this deal could have marked a shift in philosophy for the 42-year-old executive that leads to another big move.

Orioles urged to 'buy low' on Jackson Holliday extension

In an October 24 article, Bleacher Report's Kerry Miller urged the Orioles to turn their attention to signing former first-round pick Jackson Holliday to an extension this offseason.

"If the O's are savvy," Miller wrote. "They'll try to 'buy low' on his modest start with something like an eight-year, $150M extension this winter."

Sep 11, 2025; Baltimore, Maryland, USA; Baltimore Orioles second baseman Jackson Holliday (7) hits a single during the seventh inning against the Pittsburgh Pirates at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

As Miller suggests, Holliday's career hasn't gotten off to the scorching start that some expected when the highly touted prospect and son of MLB great Matt Holliday was selected first overall in 2022. After two seasons, Holliday has now played in 209 games and holds a career slash line of .229/.300/.360.

But Holliday is far from a finished product. He turns just 22 in December and has shown steady improvement while taking his licks at the big-league level after making just 218 minor league appearances. Despite the somewhat slow start, there is no reason to believe that Holliday is not the long-term answer for Baltimore at second base.

Read More: Scout affirms confidence in Orioles' young star

With that in mind, Baltimore could make the young infielder an offer similar to Roman Anthony's incentive-laden 8-year, $130M extension with the Red Sox. A deal like this would be an attempt from the Orioles to get out in front of his expected value while instilling some trust in Holliday's ability to blossom into a star player.

For Holliday, the deal can alleviate the distraction of impending free agency in 2030, while still giving him the opportunity to seek a second contract at age 30. If Elias and the Orioles are serious about making a shift to start retaining their young talent pre-arbitration following the Basallo move, Holliday's situation offers a great opportunity.