Orioles 2027 Free Agents: Who's Back, Who's Gone, Whose Option Will Be Picked Up?

It’s very obvious the Orioles need to make radical changes to their roster in 2027.

They need to overhaul the outfield, there are no two ways about it, and they need to be more open-minded than every before about rethinking their infield to get premium defenders up the middle at second base and shortstop, including moving Gunnar Henderson (at least to third base and probably to another organization, LIKE THE TWINS PLEASE). There are so many difficult decisions looming and no reason to believe that failed baseball executive Mike Elias has much of a clue about how to fix them or that these owners have any real inclination to truly compete.

The Orioles also must sort through a handful of contract options and looming free-agents, and they’d best be forthright and progressive about it. We have a read on how these guys think and how they operate and this is what we expect from their internal free agent/option decisions on a scale of: He’s Gone, He Might Be Back, He Will Be Back

Chris Bassitt – He Might Be Back

Sep 23, 2026; Baltimore, Maryland, USA; Baltimore Orioles pitcher Chris Bassitt (40) delivers a pitch during the first inning at Oriole Park at Camden Yards. Mandatory Credit: Jamie LeBlanc-Imagn Images | IMAGN IMAGES via Reuters Connect

The free-agent pitcher cannot be counted on to stay in a rotation all season at this point in his career, the $19M was a waste last year and this idea that they are guy to buy leadership and that starting pitchers are supposed to be glorified coaches is ridiculous and after the experiments with aged starters has continued to fail – Bassitt, Charlie Marton, Kyle Gibson (the second time), Zach Eflin, and given the pressure Elias is under now, we strong believe he pursues a “rental trade” (for a legit lefty, ideally) instead of going this route.

Now, if Bassitt, who was very outspoken on the way out, wants to work cheaply enough, I can’t rule it out, because Elias has a fetish for doubling and tripling down on mistakes hoping he is eventually right and looks smart.

Andrew Kittredge – He Might Be Back

Aug 29, 2026; West Sacramento, California, USA; Baltimore Orioles catcher Yohel Pozo (79) and pitcher Andrew Kittredge (39) celebrate their victory over the Athletics at Sutter Health Park. Mandatory Credit: D. Ross Cameron-Imagn Images | IMAGN IMAGES via Reuters Connect

The Orioles are definitely short a late-inning arm, and Elias believes in Kittredge in high-leverage situations like few do. And while I would be moving on and upgrading with one of these guys, it wouldn’t be out of character for Elias to try to squeeze value out of a 37-year-old, free-agent reliever. The fact Elias went back to this well after dealing Kittredge at the 2025 deadline, and opted not to deal him at this year’s deadline, gives me some pause. Kittredge was realty good from May on. Yikes.

Trevor Rogers – He’s Gone

Sep 19, 2026; Baltimore, Maryland, USA; Baltimore Orioles pitcher Trevor Rogers (28) throws during the seventh inning against the Milwaukee Brewers at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | IMAGN IMAGES via Reuters Connect

The more Rogers, a free agent, keeps talking about his time in Baltimore the more clear it becomes that he didn’t love the fact that Shane Baz got a big contract extension here before barely throwing a pitch and Kyle Bradish got an extension amid a rough season back from Tommy John surgery.

He clearly feels the Orioles never came correct with him, I’ll always contend he absolutely should have been peddled at the deadline (stop it with Elias turning comp picks into players), and in a tepid free-agent class I suspect he gets an offer that surpasses how Elias values him. My Spidey Senses tell me Elias’s lack of basic human skills and any semblance of a bedside manner have already sent this situation potentially sideways.

Zach Eflin – He’s Gone

Mar 31, 2026; Baltimore, Maryland, USA; Baltimore Orioles pitcher Zach Eflin (24) throws during the second inning against the Texas Rangers at Oriole Park at Camden Yards. Mandatory Credit: Daniel Kucin Jr.-Imagn Images | IMAGN IMAGES via Reuters Connect

Stop the madness here, please. A prime example of Elias doubling and tripling down on a mistake, running it back with him off back surgery for him to barely be able to pitch before getting shutdown again is pathetic even by Elias’s horrible standards. Bringing him back on a $24M option would be the dumbest thing Elias has ever done. Spend the money here instead.

Ryan Mountcastle – He’s Gone

Mar 19, 2026; Tampa, Florida, USA; Baltimore Orioles designated hitter Ryan Mountcastle (6) prepares for batting practice before the start of the game against the New York Yankees during spring training at George M. Steinbrenner Field. Mandatory Credit: Jonathan Dyer-Imagn Images | IMAGN IMAGES via Reuters Connect

The first baseball has been hurt for years, should have been traded when Elias and Blackjack Sig started butchering the left-field wall and he is super redundant on a roster loaded with right-handed hitting power-over-everything 1B/DH guys. There is no reason to waste $7.5M on an option here hoping to trade him. Elias blew that years ago while the entire industry was bracing for a trade.

Luis Robert – He’s Gone

Sep 3, 2026; Baltimore, Maryland, USA; Baltimore Orioles center fielder Luis Robert Jr. (88) reacts to hitting a home run as he rounds the bases against the Boston Red Sox during the fourth inning at Oriole Park at Camden Yards. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

I’ll forever be convinced this guy wanted nothing to do with Baltimore and had Elias done any homework before wasting $5M on a silly waiver claim for this outfielder he could found out before hand. All the shady late lineups coming out in Colorado, then the quick muscle injury for a guy who always has muscle injuries.

Risking $20M on him turning his career around in Baltimore and staying healthy in a place that has arguably the most dubious medical/rehab team in MLB ain’t a private equity move.

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