Orioles face key contract deadlines as baseball offseason begins

The Baltimore Orioles begin their offseason work immediately following the Milwaukee Brewers' World Series victory on Wednesday. Major League Baseball allows teams to start trading players on Thursday, and free agency opens at 5 p.m. ET on Monday, Nov. 2. These dates set a tight schedule for the club as it seeks to rebuild its roster under new General Manager Jared Banner, who was hired last week.

By Monday, the Orioles must decide whether to pick up contract options for four players. Right-handed closer Ryan Helsley will exercise his $14 million player option, according to a source who spoke to The Baltimore Banner on Thursday. Helsley signed with Baltimore last winter but played in only 15 1/3 innings and recorded eight saves due to elbow inflammation. His performance was adequate when he took the mound, but injuries limited his impact.

The club faces choices on three other options. First baseman Ryan Mountcastle has a $7.5 million club option. He played in only eight games this season because of a broken foot and an oblique strain. His 2025 slash line stood at .653 OPS in 89 games. The Banner predicts the Orioles will decline this option, making Mountcastle a free agent. Right-handed starter Zach Eflin holds a $25 million mutual option. He underwent Tommy John surgery in April and has thrown only 75 combined innings over the past two seasons. The prediction is that both sides will decline, leaving Eflin as a free agent with a $2 million buyout due.

Outfielder Luis Robert Jr. has a $20 million club option. He played three games for Baltimore before a hamstring injury ended his season. His OPS was .707 in 2026, his highest since 2023. The Orioles are expected to decline his option, triggering a $2 million buyout. Left-handed reliever Dietrich Enns has a $3.5 million team option. He was designated for assignment in May and now sits in the minors. The Orioles are predicted to decline his option, paying a $125,000 buyout.

Several players become free agents on Thursday, though the Orioles can negotiate with them exclusively until Monday night. Right-handed starter Chris Bassitt posted a 4.59 ERA in 102 innings, but he threw with a 3.74 ERA in his final eight appearances after back surgery. Reliever Andrew Kittredge finished with 11 saves and a 3.54 ERA in 48 1/3 innings. Trevor Rogers is the team's largest pending free agent and a likely candidate for a qualifying offer worth $23.15 million. Two industry sources said Rogers could earn more per year on the open market. Left-hander Keegan Akin had a 5.68 ERA in 25 1/3 innings and may seek a multi-year deal to cover his elbow recovery.

The Orioles also must act on players under team control. By Nov. 20, the club must outline its intention to offer contracts to arbitration-eligible players and others on the 40-man roster. This group includes catchers, infielders, and outfielders such as Carlos Narváez, Blaze Alexander, and Dylan Beavers. It also includes arbitration-eligible players like Gunnar Henderson, Colton Cowser, Albert Suárez, and Félix Bautista.

A lockout is expected to begin on Dec. 1 when the current collective bargaining agreement expires. Once that starts, teams cannot talk to players. The Orioles have business to conduct on every major deadline listed above, with the most immediate decisions falling on Nov. 2.