The Orioles head into the offseason with a lot of questions, and the first one is the simplest: which of their own free agents are worth bringing back?
After a disappointing season that ended with Baltimore missing the playoffs for the second straight year, the club is staring at some hard decisions. The trade of Adley Rutschman at the deadline only added to the uncertainty around where this thing is headed. So before the front office can chase upgrades, it has to sort through a group of five players whose contracts are up or who are finishing their sixth year of team control.
Trevor Rogers is the biggest name in the bunch, and the toughest call. The left-hander has had a wild two-and-a-half years in the organization.
Baltimore traded for him, barely used him at first, and sent him to the minors. Then came his second shot in June 2025, and he turned into one of the best starters in baseball.
His 2026 season got off to a brutal start, but he found his groove after a few months and finished with a strong second half. The Orioles should want him back.
The problem is that another team may simply pay more. With the 26-27 free-agent class looking thin behind Tarik Skubal, Rogers should sit near the top of the pitching market, and Baltimore may not be willing to meet that price.
Chris Bassitt looks far less likely to return. Baltimore brought in the veteran last winter to help stabilize the rotation, and while he was useful, his season didn’t match the $18.5 million deal he signed.
Bassitt made 20 appearances, 18 of them starts, and logged 102 innings with a 4.59 ERA. With a wave of younger arms approaching the majors and Bassitt entering his age-38 season, a reunion would take a major pay cut, and maybe even a move to the bullpen.
That makes a return feel unlikely.
Andrew Kittredge is in a different spot. The reliever’s path through Baltimore has already been bumpy: he signed with the Orioles two offseasons ago, was dealt to the Cubs at the 2025 deadline, and then came back in another trade last offseason.
His 2025 season was solid, but 2026 wasn’t nearly as sharp. The ERA stayed close, but he allowed more hits and struck out fewer batters in fewer innings.
He earned $9.1 million this season, and that number probably won’t hold after a year like that. A cheaper deal could make a return realistic.
Ryan Mountcastle’s future looks bleak. The first baseman played only eight games this season before injury ended his year, and he hasn’t made it through a full season since 2022. With Baltimore already leaning heavily on younger players at positions he occupies, there isn’t much reason to expect the Orioles to bring him back.
Keegan Akin may wind up back in Baltimore, but not because of a clean free-agent fit. The lefty was dependable in 2024 and 2025, posting a 3.36 ERA across 130 games over those two seasons.
This year went the other way, as he finished with a 5.68 ERA before elbow discomfort led to Tommy John Surgery. Since the surgery came in July, he is expected to miss most of 2027.
Players in that situation often return to the team they were with so they can rehab, and that could be the path here.
In Other News...
Orioles Finally Have A Young Starter Prospect Fans Can Believe In
Joseph Dzierwa has given the Orioles something they have spent years trying to identify again: a young starting pitching prospect who looks the part. The 2025 second-round pick has handled his first professional season well, moving from High-A Frederick to Double-A Chesapeake while missing bats and keeping runs off the board. His rise has been steady enough to earn a spot in the 2026 All-Star Futures Game, and it has also pushed him onto MLB Pipelines top 100 prospects list at No. 86.
For an organization that always seems to be balancing short-term contention with the long search for homegrown rotation help, Dzierwas early success matters. Scouts and analysts have pointed to both his command and his pitching mix as reasons for optimism, even if there is still debate about exactly how high his ceiling goes as a big league starter. For now, the important part is simpler: Baltimore finally has a young arm fans can follow with real belief, and the next step in his development will be one worth watching closely. [Read more 🡒]
Orioles Nearly Pulled Off An Adley Rutschman Blockbuster With The Yankees
Adley Rutschmans name surfaced in a conversation that would have jolted the Orioles and the rest of the American League: Baltimore reportedly checked with the Yankees on a possible swap built around its star catcher. The framework, according to the report, would have sent Rutschman to New York in exchange for several Yankees pieces, including Austin Wells, Elmer Rodriguez, Yostin Pena, and either Will Warren or Ryan Weathers.
In the end, the Yankees passed, leaning on Wells game-calling and the value of their bullpen depth as they position for the postseason. For Baltimore, the episode underscores how closely the market can circle around one of the franchises most important players, and it leaves open the possibility that New York could circle back to its catching plans once the season is over. [Read more 🡒]
Orioles Suddenly Have A Bigger Luis De Len Decision Ahead
Luis De Lens late-season cameo gave the Orioles something to think about well beyond September. The clubs No. 7 prospect worked eight relief appearances and posted a 1.93 ERA, enough to draw praise from manager Craig Albernaz and put his name in a more prominent place in the organizations pitching conversation.
The plan remains for De Len to report to spring training as a starter, but Baltimores rotation picture could soon push the discussion in another direction. If Trevor Rogers departs in free agency, the Orioles may need to add a left-handed starter, and with most of the current rotation options coming from the right side, De Len suddenly sits at the center of a decision that could shape how the staff is built. [Read more 🡒]