The Orioles’ offseason starts with a stack of choices, and the clock is already ticking.
With the Brewers crowned World Series champions on Wednesday night, baseball immediately flips into winter mode. Major league teams can start trading on Thursday, free agency opens soon after, and Baltimore has a full slate of roster business to handle under new general manager Jared Banner, who was hired last week.
The biggest calendar markers come fast. By Monday, Nov. 2, all contract options have to be resolved, and teams also must notify players on qualifying offers.
Free agency opens by Monday night, generally at 5 p.m. ET, though clubs can exclusively negotiate with their own expiring-contract players from Thursday through Monday.
Then comes Nov. 17, the deadline for players to accept or decline qualifying offers at 4 p.m. ET.
Nov. 20 is the non-tender deadline for unsigned players still under team control on the 40-man roster, including arbitration-eligible players. Dec. 1 brings the expiration of the current collective bargaining agreement, and a lockout is expected to start then.
Baltimore has decisions on all of those fronts.
One player already has made his choice. Right-handed closer Ryan Helsley will exercise his $14 million player option, a source told The Banner on Thursday.
Helsley was brought in last winter to handle the ninth inning, and although two bouts of elbow inflammation limited him to 15 1/3 innings and eight saves, he was solid when he did pitch.
The Orioles also have several options of their own to weigh.
First baseman Ryan Mountcastle has a $7.5 million club option, but the fit looks shaky. Mountcastle, 29, appeared in only eight games this season after a broken bone in his foot and an oblique strain during rehab.
He once looked like a middle-of-the-order force, smashing 33 home runs in 2021, but his production has faded and he finished 2025 with a .653 OPS in 89 games. The Banner prediction: the club declines, sending Mountcastle into free agency.
Right-hander Zach Eflin is sitting on a $25 million mutual option, the kind that almost never gets picked up by both sides. Eflin’s April Tommy John elbow reconstruction surgery makes the decision even easier to read, with his recovery likely to stretch into 2027 and leave him headed for the injured list to start that season.
Between 2025 and 2026, he threw just 75 combined innings. The Banner prediction: the option is declined, he becomes a free agent, and he receives a $2 million buyout.
Outfielder Luis Robert Jr. arrived late as Baltimore tried to push for the postseason, but his stay was short. He played three games, then went on the injured list and missed the rest of the year with a hamstring injury.
His career trajectory has been shaped heavily by injuries, and his 2026 OPS between the Mets and Orioles was .707, his best mark since 2023. He carries a $20 million club option, but The Banner predicts Baltimore passes and Robert becomes a free agent, owed a $2 million buyout.
Left-handed reliever Dietrich Enns has a $3.5 million team option, though he’s no longer on the 40-man roster after being designated for assignment in May and then accepting an outright assignment to the minors. In the majors, he posted a 3.94 ERA over 16 innings.
In Triple-A, the numbers were rougher, with a 5.80 ERA in 54 1/3 innings. The Banner prediction: the Orioles decline, and Enns hits free agency with a $125,000 buyout.
Beyond the options, Baltimore has a group of pending free agents who can start negotiating elsewhere once Thursday arrives, even if the Orioles get a window to keep talks exclusive through Monday night.
One of them is the 37-year-old starter, who bounced back after midseason back surgery and finished his first year in Baltimore with a 4.59 ERA over 102 innings. He was better down the stretch, posting a 3.74 ERA in his final eight outings.
Right-handed reliever Andrew Kittredge gave the Orioles steady work all season, finishing with 11 saves and a 3.54 ERA in 48 1/3 innings.
Trevor Rogers is the biggest name in that group. The left-handed starter is a likely candidate for a qualifying offer, which would be worth $23.15 million for one year. Still, two industry sources speaking on the condition of anonymity to discuss the market said Rogers likely could earn more than that on a per-year basis in free agency.
Left-handed reliever Keegan Akin also heads to free agency after July elbow surgery that will keep him out for much of next season as well. The 31-year-old may have to think bigger-picture in the market, perhaps seeking a two-year deal that gives him time to rehab through much of 2027 before returning. He struggled in 2026, putting up a 5.68 ERA in 25 1/3 innings.
Then there are the players still under Baltimore control, with the Nov. 20 non-tender deadline looming for those on the 40-man roster who have not yet reached arbitration or the level of salary control that comes with it.
Among the pre-arbitration group are catcher Carlos Narváez, outfielder Dylan Beavers, and pitchers Brandon Young, Grant Wolfram and Rico Garcia.
The arbitration-eligible group includes infielders Jordan Westburg, in his first year of eligibility, and Gunnar Henderson, in his second, along with outfielder Colton Cowser in his first year and Leody Taveras in his third and final year.
In Other News...
Orioles Still Have One Obvious Outfield Problem After Latest Roster Moves
The Orioles kept trimming and sorting their roster this week, a familiar offseason task for a club trying to balance flexibility with a clear need in the outfield. Jos Barrero and Albert Surez cleared waivers and chose free agency, Colin Selby was reinstated from the injured list and sent to Triple-A Norfolk, and Codi Heuer accepted an outright assignment to Norfolk, leaving Baltimore with 33 players on the 40-man roster.
Luis Robert Jr. remains the most notable name in the middle of it all, because the Orioles moved on from his contract option and sent him into free agency. Even after the latest roster moves, the outfield still looks like a spot Baltimore will have to keep addressing, and the front office now has room to keep working on it without forcing a decision just yet. [Read more 🡒]
Orioles Just Turned Luis Robert Jr Into An Offseason Debate
Luis Robert Jr.'s Baltimore stint never really got the chance to get going, and now it has already become an offseason decision point. The Orioles have declined his 2027 team option, another sign of how aggressively they are sorting through their roster after a season in which they also moved on from several other players' options for next year.
Robert was claimed off waivers from the Mets in 2026, but injuries kept him from making much of an impact in Baltimore. He appeared in only three games for the club before ending up on the injured list, and the stop-start season left the Orioles with little choice but to treat his future as part of a broader reset rather than a simple return plan. [Read more 🡒]
Orioles Hold A Luis Robert Decision That Could Help Boston
Bostons offseason planning already has a familiar name in the mix, and it comes with a Baltimore wrinkle. Luis Robert Jr., now with the Orioles, is one of the offensive options the Red Sox are weighing as they look ahead to building a club that can contend in 2027, especially if they wind up moving Jarren Duran and need another dynamic outfield bat to consider.
Robert still carries the appeal that made him an All-Star in the first place, with power and speed that can change a lineup in a hurry. The concern, as always, is whether the health questions that have followed him in recent years will keep him from becoming the kind of dependable target Boston would want before committing to a major pursuit. [Read more 🡒]