The Orioles are already trimming their 40-man roster as they brace for what could be a shorter-than-usual offseason, with the Collective Bargaining Agreement set to expire and a lockout expected to begin on December 1. That squeeze makes Jeremiah Jackson one of the more interesting names to watch.
Jackson’s path to Baltimore was never exactly linear. He spent four seasons stuck in Double-A across three organizations - the Los Angeles Angels, New York Mets and Orioles - before a need opened up at Triple-A Norfolk.
At 25, he finally got his first real taste of that level and made the most of it. He hit .254 with a .703 OPS, four home runs and 19 RBIs in 45 games at Chesapeake, then took off at Norfolk, batting .377 with a 1.073 OPS, 11 homers and 22 RBIs in 40 games.
That surge earned him a real look, even if the Orioles hadn’t seen much of him. He had been invited to major league spring training, but was sent back to minor league camp quickly. Then Ramón Urías was traded in July 2025, Baltimore needed another infielder, and Jackson got his shot over the final two months.
He handled it well enough to force attention. After getting time at right field and third base, he opened August hot, hitting .323 with an .828 OPS. September was quieter, with a .221 average, but his overall line - .276 with a .775 OPS, five homers and 21 RBIs - was strong enough to put him on the radar for spring training again.
The Orioles also needed him early in 2026. With Jackson Holliday and Jordan Westburg injured, Jackson made the club and started fast.
His most unforgettable moment came on April 14, when a foul ball broke manager Craig Albernaz’s jaw in the fifth inning. One inning later, with Albernaz back in his office, Jackson launched a grand slam that helped the Orioles rally past Arizona 9-7.
That win left Baltimore at 9-7, and it would turn out to be the only time all season the club was two games over .500.
By April 30, Jackson was hitting .270 with a .768 OPS, six home runs and 24 RBIs. But the playing time shifted once Holliday returned in mid-May after right wrist surgery in February. Jackson’s chances at second base thinned out after that.
The second half was rough. In July, he went 0-for-25, and on August 19 he was optioned to Norfolk when catcher Samuel Basallo came off the injured list. The Orioles chose to carry three catchers, and Jackson headed back to Triple-A.
He returned on September 9, but the bat never really came back with him. He hit .111 the rest of the way and finished the season at .217 with 10 home runs, 45 RBIs and a .611 OPS. His lone real late-season highlight came on September 25, when he hit an inside-the-park home run.
The numbers tell the story of a player who lost too much of the strike zone and too much of the defensive edge. In 2025, Jackson walked 11 times and struck out 50.
This year, he struck out 69 times and walked only 10 times. His on-base percentage fell from .328 to .247.
At second base, where he played 80 games, he led the American League with 10 errors.
Baltimore still needs outfield help, but Jackson barely got any run there in 2026, starting four games in left and one in right. If Holliday and Westburg are both back, Blaze Alexander could see more time at second against left-handed pitching, which would make Jackson’s path even narrower.
Alexander can also handle all three outfield spots, plus second, third and shortstop. Jackson played 13 games at third in 2025, but with Alexander, Mayo and Christian Encarnacion-Strand all filling in there, he logged just one inning at the position this season.
Jackson does still have two options left, but after an uneven offensive year, his fit on the 2027 Orioles looks shaky.
There is also another infield name pushing into the conversation. Aron Estrada played second base at Chesapeake and showed real pop, hitting 25 home runs with 81 RBIs while batting .281 with an .807 OPS between Chesapeake and Norfolk. The issue is defense, which is not considered a strength.
Baltimore has to make room somewhere, and Jackson’s spot on the 40-man roster no longer looks secure.
In Other News...
Orioles Face A Tough Ryan Mountcastle Decision Today
Ryan Mountcastles future with the Orioles is suddenly one of the more interesting decisions on the clubs offseason to-do list, with his 2027 contract option coming due and the front office weighing how to handle a player who has long been part of the lineup picture. Mike Elias had previously sounded confident about Mountcastles place in the organization, but the conversation has shifted as the roster has changed around him and the injury concerns have piled up.
Mountcastles season was interrupted by a fractured left foot and a severe oblique strain, the kind of setbacks that complicate any long-range planning for a team trying to balance talent, health and payroll. Baltimore still has to sort through whether his upside and track record are worth keeping in place, and the decision carries enough weight to say something about how the Orioles view the next phase of their roster construction. [Read more 🡒]
Orioles Just Made A Tough Call That Could Be The Start
The Orioles offseason trimming has already started to reshape a roster that once looked built around a wave of young talent. Heston Kjerstad, a former first-round pick who had not yet turned his Triple-A success into sustained production in the majors, was released after clearing waivers, closing a chapter that never quite got off the ground in Baltimore despite his strong showing in Triple-A this past season.
Ryan Mountcastles future is now part of the same conversation, too, after the club declined his contract option for 2027. It is the kind of move that signals a front office willing to make hard choices early, even with familiar names involved, and it leaves the Orioles with more questions than answers about how much of their recent core will still be in place when they next try to push back into contention. [Read more 🡒]
Orioles Offseason Cleanup Is Forcing A Tough Roster Call
The Orioles offseason housekeeping kept moving this week, with roster spots and contract decisions starting to come into focus as the front office sorts out the edges of the roster. Colin Selby and Codi Heuer are still in the system, and the club is also expected to extend a qualifying offer to Trevor Rogers, part of the usual late-fall churn that can quietly shape the winter ahead.
The bigger choice on the immediate horizon is Ryan Mountcastle, whose $7.5 million team option gives Baltimore a straightforward but meaningful decision point as it weighs payroll, depth and fit. Around the league, award season also got rolling with BBWAA finalists and Silver Slugger nominees announced, while former Oriole Christian Walker added another Gold Glove to his rsum, a reminder of how many familiar names keep surfacing as the Orioles own roster puzzle gets sorted out. [Read more 🡒]