Orioles Offseason Preview: Which Free Agents Return, Who Leaves, and Who Replaces Them?

By Charles Harris

The Baltimore Orioles have some major decisions to make this offseason, and Mike Elias cannot afford to get them wrong. If Baltimore wants to bounce back in 2027, the front office must decide which veterans are worth bringing back, which players have reached the end of their time in Birdland, and where the organization needs to spend its money.

Trevor Rogers, Chris Bassitt, Andrew Kittredge, Zach Eflin, Ryan Mountcastle, and Ryan Helsley all represent different challenges for the Orioles. Some could help stabilize the pitching staff, others come with significant questions about health or performance, and one has a contract decision that could shape the bullpen.

My Ravori Sports position is simple: Baltimore cannot afford to make offseason decisions based on sentiment. The Orioles need reliable starting pitching, a deeper bullpen, and a roster built to compete—not a collection of familiar names.

The return percentages and contract estimates below are my projections, not reported negotiations or confirmed offers.

1. Trevor Rogers — Starting Pitcher

Chance of returning: 20%

Projected contract if he stays: 5 years, $100 million–$120 million

Trevor Rogers is one of the most important names on Baltimore's offseason list, but I believe an Orioles reunion is unlikely. Rogers has the potential to command a significant contract, and the Orioles must decide how much they are willing to invest in a starting pitcher when other areas of the roster also need attention.

Rogers has shown that he can be an important part of a rotation, but the business side of baseball can change everything. If another team is willing to offer him a more attractive contract, a larger guarantee, or a better long-term opportunity, Baltimore could find itself watching him leave.

I would put his chances of returning at just 20%. That does not mean the Orioles should avoid making an offer. It means the organization should prepare for the possibility that Rogers will be wearing another uniform in 2027.

If Baltimore does manage to keep him, I could see a deal in the neighborhood of five years and $100 million, with the final number potentially climbing toward $120 million depending on the market. That is a projection, not a reported asking price. The Orioles would need to be comfortable committing significant money to a pitcher over multiple seasons.

But if Rogers leaves, Mike Elias cannot simply expect another member of the rotation to take his place. The Orioles should pursue a legitimate starting-pitching upgrade through free agency or the trade market. A pitcher such as Framber Valdez, if available and financially realistic, could be a replacement target. Baltimore should also consider younger starters who offer durability and more years of team control.

The worst outcome would be allowing Rogers to leave without having another dependable starter lined up.

My verdict: Rogers is unlikely to return, and the Orioles need to prepare accordingly. If he leaves, Baltimore must reinvest in the rotation rather than pretending the loss will not matter.

2. Chris Bassitt — Starting Pitcher

Chance of returning: 15%

Projected contract if he stays: 1 year, $8 million–$12 million

Chris Bassitt brings experience, a deep repertoire, and a veteran presence to a pitching staff. Those qualities can be useful for a team trying to return to contention, but the Orioles have to weigh his age and recent performance against the cost of bringing him back.

Baltimore needs starting-pitching depth, especially with the uncertainty that comes with injuries and young pitchers developing at different speeds. A veteran who can take the ball every fifth day has value, but only if he can provide dependable innings.

I give Bassitt a 15% chance of returning. The Orioles should not automatically offer him another expensive contract simply because he has experience. They need to evaluate whether his expected production justifies the commitment.

If Bassitt wants to return, I would consider a one-year deal worth $8 million to $12 million, potentially with incentives. That would give Baltimore some veteran insurance without locking the organization into a long-term commitment.

If he leaves, the Orioles should target a younger mid-rotation starter or explore a trade for a pitcher with multiple years of team control. The objective should be to improve the rotation, not simply replace one veteran with another.

My verdict: Bassitt should be a secondary option, not the centerpiece of Baltimore's offseason pitching strategy.

3. Andrew Kittredge — Relief Pitcher

Chance of returning: 20%

Projected contract if he stays: 1 year, $5 million–$7 million

Andrew Kittredge could provide useful bullpen experience, but Baltimore needs to be careful about how much it spends on veteran relievers. Bullpen performance can fluctuate considerably from season to season, and the Orioles need several dependable options rather than relying on one or two arms.

I give Kittredge a 20% chance of returning. If the price is right, he could help provide depth and take pressure off the younger members of the bullpen. But Baltimore should not get into a bidding war to keep him.

My proposed contract would be one year for $5 million to $7 million, with incentives tied to appearances or performance. That arrangement would give the Orioles some flexibility while keeping the financial risk relatively limited.

If Kittredge leaves, Baltimore should look for a durable setup reliever who can miss bats, limit walks, and handle high-leverage situations. The team should also consider acquiring a reliever with multiple years of team control.

The Orioles cannot afford another season in which the bullpen lacks enough reliable arms to protect leads late in games.

My verdict: Bring Kittredge back only at a reasonable price. If another team offers more, Baltimore should move on and invest in improving the bullpen as a whole.

4. Zach Eflin — Starting Pitcher

Chance of returning: 10%

Projected contract if he stays: 1 year, $5 million–$8 million with incentives

Zach Eflin's situation is complicated by his health and the financial implications of his option. When healthy, he can provide valuable innings, but Baltimore cannot make a major commitment without knowing when he will be ready to contribute.

I give Eflin only a 10% chance of returning. The Orioles have to be realistic about the risks involved in committing substantial money to a pitcher whose availability is uncertain.

If Eflin wants to continue his career in Baltimore, I would consider a much cheaper incentive-based contract. A one-year deal worth $5 million to $8 million, with additional money tied to innings pitched and availability, would be more reasonable than committing to a large guarantee.

If Eflin leaves, the Orioles should pursue a durable starter who can be expected to contribute early in the season. They cannot enter spring training hoping that a recovering pitcher will be ready to fill a regular rotation spot.

My verdict: Avoid the expensive commitment. If Eflin returns, it should be on a deal that reflects the uncertainty surrounding his health.

5. Ryan Mountcastle — First Baseman

Chance of returning: 10%

Projected contract if he stays: 1 year, $3 million–$5 million

Ryan Mountcastle has been part of the Orioles organization for years, and he has shown that he can provide right-handed power. But his recent injury concerns and Baltimore's current roster construction make his future uncertain.

The key question is whether the Orioles should exercise his $7.5 million club option. At that price, Mountcastle needs to offer a clear role and enough expected production to justify the commitment. Baltimore also has Pete Alonso occupying a major role at first base, which makes the playing-time picture more complicated.

I give Mountcastle a 10% chance of returning under his current option. If the Orioles decline it, I would not completely rule out a reunion at a lower salary.

A one-year contract worth $3 million to $5 million, potentially with incentives, could make sense if Mountcastle is healthy and willing to accept a more flexible role. But the Orioles should not promise him everyday at-bats just because he has been with the organization for a long time.

If Mountcastle leaves, Pete Alonso should handle much of the first-base workload. Baltimore could use the opportunity to add a right-handed bench bat or a versatile hitter who can contribute at multiple positions.

My verdict: Decline the expensive option and consider a lower-cost reunion only if the medical outlook and roster fit make sense.

6. Ryan Helsley — Relief Pitcher

Chance of returning: 90%

Expected 2027 salary: $14 million player option

Ryan Helsley is different from the other names on this list because his player option gives him significant control over the decision. I expect him to return if he exercises the option, although his health will be a major factor in determining how much he contributes.

Helsley has the kind of power arsenal that can make him an important late-inning weapon. However, Baltimore needs to see him return to health and perform consistently before treating him as the unquestioned answer at the back end of the bullpen.

I give Helsley a 90% chance of returning, assuming he exercises his $14 million player option. The Orioles should plan around his potential contribution while making sure they have other options available.

If Helsley is healthy, he could work alongside Félix Bautista and give the manager more flexibility in high-leverage situations. But the Orioles cannot build their entire bullpen strategy around two pitchers and hope both remain healthy all season.

If Helsley does not return, Baltimore should explore the market for an established late-inning reliever. David Bednar would be a potential target if available at a reasonable cost, although the Orioles should compare multiple options before making a commitment.

My verdict: Plan on Helsley returning, but add another reliable late-inning arm. Baltimore needs depth, not another season of crossing its fingers when the bullpen door opens.

Final Ravori Sports Predictions

Player	Chance of return	Projected contract or decision
Trevor Rogers	20%	5 years, $100M–$120M
Chris Bassitt	15%	1 year, $8M–$12M
Andrew Kittredge	20%	1 year, $5M–$7M
Zach Eflin	10%	Lower-cost, incentive-based deal
Ryan Mountcastle	10%	Decline option; consider cheaper reunion
Ryan Helsley	90%	Expected to exercise $14M player option

These are offseason projections, not confirmed team decisions or reported offers.

The Bottom Line: Mike Elias Has Work to Do

The biggest question is what Baltimore will do if Trevor Rogers leaves. I believe that outcome is more likely than an Orioles reunion, and the front office must have a serious replacement plan ready. Losing a key starter without bringing in another dependable arm would put even more pressure on the rest of the rotation.

Helsley is likely to return under his player option, but Baltimore still needs to strengthen the bullpen. Bassitt and Kittredge should be considered only at the right prices, Eflin's health makes a large commitment difficult to justify, and Mountcastle's future depends on his cost and role.

Mike Elias has to prove that the Orioles can make disciplined financial decisions while still spending enough to compete. This is not about bringing everyone back because fans recognize their names. It is about building a roster that can win consistently in 2027.

Birdland, what would you do? Should the Orioles make one last push to keep Trevor Rogers, or is it time to move on and spend that money on a different starting pitcher? And with Ryan Helsley potentially returning, how many more bullpen arms should Baltimore add?

The answers will help determine whether the Orioles are serious about getting back into contention—or preparing for another offseason of excuses.

— Ravori Sports