The Orioles have not dallied this offseason. Baltimore enters the winter meetings Monday in Orlando, Florida, as one of Major League Baseball’s most aggressive teams thus far, according to industry sources, and there is ample time remaining for additional moves.
Whether the Orioles turn that perceived aggression into major monetary commitments remains to be seen. It takes two sides to lock in a deal, and for every player the Orioles are targeting, multiple other teams are preparing their own offers.
What is clear, however, is that Baltimore is attempting to fix some of the issues that derailed 2025.
The Orioles have begun rebuilding their bullpen by reacquiring right-hander Andrew Kittredge and signing right-hander Ryan Helsley to a two-year, $28 million contract that includes an opt-out clause. They also traded for outfielder Taylor Ward, expending starting pitching depth in the form of Grayson Rodriguez to do so.
The largest item on Baltimore’s to-do list remains acquiring starting pitching, and the winter meetings may lead to a critical breakthrough as the baseball world descends on Central Florida.
President of baseball operations Mike Elias said the Orioles are interested in just about every starting pitcher available, be that in free agency or via trade. They have expressed particular interest in left-hander Ranger Suárez and right-handers Michael King and Tatsuya Imai, according to sources.
And MLB.com indicates the Orioles are in on left-hander Framber Valdez. Baltimore also remains in the mix for designated hitter Kyle Schwarber, according to the New York Post, and the Orioles are expected to add more bullpen pieces.
The Toronto Blue Jays, by far, have been the most aggressive team, having landed right-hander Dylan Cease with a seven-year, $210 million contract that sets the table for what should be a vibrant starting pitching market. The Boston Red Sox, another American League East rival, have swung two trades, one of which brought right-hander Sonny Gray to Fenway Park.
There will never be a shortage of aggression from AL East franchises. The Orioles are often one of the most risk-averse of those organizations. But, as Baltimore pushes for splashes this winter, there is surprise from some industry sources regarding what the Orioles have done thus far — and what they may be willing to do.
“I am stunned,” one agent from a prominent firm said, before adding that the early movement to acquire Ward and Helsley is “so unlike the Orioles.”
Another agent who has dealt with the Orioles this winter in contract negotiations said the front office has appeared particularly decisive when targeting players the team believes in. From this agent’s perspective, Baltimore didn’t hesitate once the front office decided to move in that direction.
And a third agent said he has found the Orioles to be very willing to deal, perhaps best displayed by their decision to move on from Rodriguez, despite the right-hander maintaining four years of team control. Asked whether that shows more urgency than previous years, the agent quipped, “I’m not sure Mike ever shows urgency.”
Still, there are signs that past lessons have been learned — a disappointing 2025 campaign, which included a slow start and the firing of manager Brandon Hyde, displayed the holes that riddled a homegrown roster. It began, primarily, with dismal performances from the rotation. But, as the season went on, the inconsistencies of the lineup spelled trouble.
With that in mind, Baltimore worked quickly to land Ward, whom the Orioles deem will elevate their lineup from the right side of the plate. Ward is coming off a career-high 36 homers for the Los Angeles Angels. He’s under team control only for 2026; trading four years of Rodriguez (albeit with injury concerns) for one year of Ward in itself shows an aggression not frequently seen under Elias.
But the moves are far from finished. Elias has targeted multiple starting pitchers and maintains in the mix in the outfield market. Baltimore is interested in Schwarber, too, although as a fourth agent said, speaking on the condition of anonymity to freely discuss the market, Elias is “going to have to go outside his financial modeling to get players like Schwarber.”
“They have to get starting pitching,” that agent continued, and that seems to be the top priority for Baltimore after acquiring Helsley and Ward. The issue, though, is that a high-level starter is not the only glaring need, the agent said.
“The outfield looks like a mess,” the agent said, especially in terms of defense.
The Orioles moved quickly to acquire Taylor Ward, who hit 36 home runs in 2025. (Jayne Kamin-Oncea/Getty Images)
Tyler O’Neill, who could improve after an injury-riddled season in which he played 54 games, did not perform well at the plate or in the field in his first year in Baltimore. Dylan Beavers could develop into a strong corner defender, and Ward is an average corner outfielder.
Colton Cowser, meanwhile, has a tall task handling center field, if that is the way the outfield shakes out at the end of the offseason.
The infield, not including first base, seems more settled with Gunnar Henderson, Jackson Holliday and Jordan Westburg, among others. The first base mix of Ryan Mountcastle, Coby Mayo and Samuel Basallo could change if there is a trade. That leaves the outfield as the main positional unit with room to augment.
As the winter meetings arrive, the fourth agent acknowledged the early moves but noted that, until the Orioles make a major splash, it’s difficult to take their claims that there are no monetary constraints seriously. Owner David Rubenstein has repeated that claim, but while payroll has risen, the team hasn’t made a franchise-altering addition — the kind that lasts many years.
Cease, for instance, signed for seven years. The latter part of that contract may not be good value, but that is the cost of landing a high-end free agent pitcher.
The Orioles have only recently handed multiyear deals to free agents, and even those hold caveats. The three-year contract for O’Neill — the first multiyear free agent contract for Elias — held an opt-out after the first season. Had O’Neill performed at a high level, he likely would have returned to the open market. And Helsley’s two-year deal also contains such a clause, which leaves Baltimore in a similar position to the one it was in with O’Neill. A strong year may lead to Helsley opting out.
Each of the available starting pitchers will warrant a large contract, even though Imai’s track record has been in Japan. Valdez and Suárez would be clear front-line starters to pair with Kyle Bradish and Trevor Rogers; there are more questions about Imai’s ability to adapt quickly and King’s health (he missed almost four months in 2025 due to shoulder and knee injuries).
Spending doesn’t necessarily lead to results, but the Orioles have an obvious need in their rotation. This week could include movement toward filling that absence.