The Winter Ahead

The Orioles are 72-78 with twelve to play, fifth in the American League East, and while they still aren’t mathematically eliminated  (4GB of the 3rd Wild Card) the off-season is quickly approaching.

Last winter saw Pete Alonso signed for five years and $155 million. Ryan Helsley for two and $28 million. Shane Baz in a trade. Zach Eflin, Taylor Ward, Leody Taveras. Payroll to $163 million, the highest in franchise history. David Rubenstein opened the checkbook and Mike Elias spent it.

They’re 18.5 games behind Tampa Bay.

So the winter ahead matters more than the last one did. There’s a thread running on the BSL board right now where a dozen people have laid out their wish lists, and I want to start by saying something that isn’t a criticism of any of them: everybody already knows what the needs are. Top-of-rotation starter. Outfield defense. Two bullpen arms. A catcher who isn’t an automatic out. Decisions on Holliday and Mayo. Every list in that thread has most of those, in roughly the same order.

I’m assuming two things for the rest of this: Elias is back, and there will be baseball in 2027. Neither is guaranteed.

The Calendar Problem

The collective bargaining agreement expires at 11:59 p.m. on December 1st.

The owners want a salary cap, which has never existed in this sport and which the union has opposed under every executive director it has ever had. Bruce Meyer, who took over as interim head of the MLBPA in February, has said flatly that the union’s position isn’t changing. Most people who cover labor in this sport expect a lockout.

What that means practically: free agency may open, run for a few weeks, and then freeze. Transactions stop during a lockout. The 2022 version lasted 99 days and pushed Opening Day back a week.

I’m assuming it gets resolved. But it changes how you read everything below. Teams that want to do business may try to do it fast, in November, before the door closes. Teams that would rather wait now have a structural excuse to wait.

A front office that has been criticized for years for being too patient has just been handed the best alibi it will ever get.

The Money

Per FanGraphs’ RosterResource, the Orioles have $74.3 million in guaranteed money on the books for 2027. They spent $162.8 million in 2026.

Here’s what’s actually committed:

• Pete Alonso — $33.5M, and it stays there through 2030
• Tyler O’Neill — $16.5M
• Kyle Bradish — $10M, the first year of a five-year, $90 million extension
• Shane Baz — $7.8M, year two of five years and $68 million
• Yennier Cano — $2.75M
• Samuel Basallo — $1.625M
• Zach Eflin buyout — $2M

That’s the list.

Coming off the books: Chris Bassitt ($18.5M), Andrew Kittredge ($9M), Trevor Rogers ($6.2M), Zach Eflin ($8M), Keegan Akin ($3M).

Now add the things that aren’t in that $74.3 million. Ryan Helsley holds a $14 million player option and there is no chance on this earth he declines it after throwing 15 innings. Gunnar Henderson goes to his second arbitration year off an $8.5 million salary. Félix Bautista, Jordan Westburg, and Colton Cowser all enter arbitration.

Call it roughly $124 million of realistic commitment once you tender everyone and fill out the roster. At a flat $163 million payroll, that’s about $39 million of room.

The luxury tax isn’t a factor in any scenario. Their 2026 CBT number was around $215 million against a $244 million first threshold.

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1. Land Casey Mize, and Re-sign Trevor Rogers

Trevor Rogers is a free agent — he’s second on the Orioles in fWAR this season at 3.3. He’s thrown 157 innings, posted a 3.64 FIP, and cost $6.2 million.

That leaves Baz, Bradish, Brandon Young, and two openings.

You can make the argument that the O’s should be pursuing Tarik Skubal. He is not qualifying-offer eligible, because he was traded in-season to the Dodgers. No draft pick. No international money. Just cash.
I’ve made the point plenty of times over the years that the O’s being built as they were gave them payroll flexibility.
You’d like to use that flexibility the one Winter where one of the best pitchers alive is available with no draft-pick tax attached.

Living in reality, let’s forget about the Skubal pipe dream, and set our sights on Casey Mize.
CBS Sports recently identified Baltimore as a potential landing spot for Mize, and he’s someone that does seem reasonably obtainable.

I’d also like to re-sign Rogers. He’s had success here, he’s talked about wanting to stay here. I don’t see the O’s obtaining two pitchers better than him.

A Bradish, Mize, Rogers, Baz, Young rotation looks capable.

 

2. Decide On Gunnar Henderson

Two years of control left. Arbitration in 2027, arbitration in 2028, free agent after that.

Personally, I don’t think there is a lot to decide here.

He’s the most talented overall player on the roster, and 2026 was overall a down year.

If his 2026 season looked like his 2024 season, I think there would be a strong argument for moving him this Winter – if the O’s know an extension isn’t happening.

But given the season he’s had, I’m not real interested in moving him this Winter.

Run it back for ’27.  If he and the team rebound, great.
If he rebounds, and the team doesn’t; then you can move him next Summer like you did with Rutschman at the Trade Deadline this year.

The only logical contrarian point of view would be if the Orioles don’t believe there is any circumstance where they contend next year.
If they don’t believe they can contend, then you could say you’re better off trading him with 2 full years of team control remaining vs. 1.5, even coming off a down year.

3. Fix The Outfield Corners — Not The Outfield

Several people want a whole new outfield with Cowser on the bench. That’s not going to happen.
He’s been strong defensively in CF, and it’s highly likely that’s where he is to begin ’27.

What do you want the O’s to do with LF and RF?

How do you evaluate Dylan Beavers?
He runs well, he throws well, but this year his defense has been poor (-7 Outs Above Average).
Last year he graded right around average.
This Spring Orioles Manager Craig Albernaz said Beavers had all of the tools necessary to be an above average defensive OF.

What do the O’s believe about Beavers now?
If they don’t believe Beavers can be average defensively, then maybe the O’s go after a corner OF like Daulton Varsho, or Seiya Suzuki.

Should also be noted that the O’s have the $20M team option on Luis Robert Jr, or a $2M buyout.

Heston Kjerstad has gotten back to the Majors after spending nearly all of ’26 at AAA.
Tyler O’Neill is on the IL with a shoulder injury. He’s owed $16.5M next year.  He was hitting LHP well before going to the IL, but the O’s would still have to eat most of his contract to move him.
Do they think Coby Mayo can handle RF?  He’s got the arm, and a short RF at-least at OPACY.  Is Mayo in RF even on their radar?

Enrique Bradfield has continued to slide down the Orioles Top 30 Prospect list.
Currently the 2023 1st round pick is the O’s 18th overall top prospect according to MLB.com.
Bradfield played in 108 games in 2024, 76 games in 2025, and 94 so far in 2026.
He’s got a .705 OPS in 302 ab’s at AAA this year.
Even if you wanted to pencil in Bradfield’s defense and speed in CF next year, and move Cowser to LF; Bradfield hasn’t shown an ability to stay available.
Also, if he’s a .600 OPS guy in the Majors, could the everyday lineup sustain that even with excellent CF defense?

4. Sign Ryan Jeffers

Jeffers is the tenth-best free agent in this class per CBS. He turned 29 in June, and has an .856 OPS for the year – hitting both LH and RH pitching.

I don’t think the O’s are real excited about giving Basallo 110+ starts behind the plate.
If that’s the case, than you need less of a backup and more of a guy that splits Catcher with Basallo.

Maybe the O’s believe Carlos Narvaez will rebound?
He’s got a sub .500 OPS this year over 237 ab’s, but he did have 42 xbh’s in 2025, and he is a quality defender.

I could see the O’s believing a Narvaez rebound is a better utilization of the money they have available vs. an investment in Jeffers.
That’s fine if that’s the calculation, but the O’s have to get that call right.

If Basallo is only going to catch 80-90 games, they can’t have a complete no-hit backup behind him.

How much would Jeffers cost? $15M a year for 2-3 years?

5. Can You Obtain At-Least One High-Leverage Bullpen Arm?

Andrew Kittredge is a free agent. Helsley opts in at $14 million after 17 appearances. Félix Bautista hasn’t thrown a major league inning all year – he and Helsley each worked an inning at Norfolk on Saturday, Helsley’s first appearance since June 27th.

Bautista is in his final arbitration year in 2027 and a free agent after it. The Orioles get one season to find out what The Mountain is after two shoulder surgeries and two lost years.

Yennier Cano is signed for two more years at $7.5 million total and has been the best reliever on the team. Beyond that it’s Rico Garcia, Grant Wolfram — whose 4.75 ERA hides a 2.74 FIP and a quality strand rate.
Can also talk about Anthony Nunez, Alex Hoppe, Cam Sanders, Josh Walker.  Maybe they bring Kittredge back.

If one of Helsley or Bautista is back next season and All-Star caliber, that goes a long way.
If their both effective, that would obviously be huge for the O’s.

I feel reasonably good right now that they could contribute to the O’s in ’27.
But if I’m the O’s, I go into the off-season not planning on relying on either.

I can buy Skubal as one of the games best starters being priced out of any realistic scenario for the O’s.

I’d like to think they could make a strong offer to one of the games better relievers like Adrian Morejon.
Clearly Morejon will be in-demand by many. Maybe you can’t convince him to come to Baltimore.
You can make him turn you down.

Another Free Agent option would be David Bednar.

Obtaining either in Free Agency would move the needle.

If you can’t obtain one of those two in Free Agency, then you have to consider moving one of your internal positional players via trade for a reliable high-leverage arm.

6. What Do The O’s Want To Do With The Infield?

Pete Alonso has 1st for years to come.

I’d probably keep Jackson Holliday.  He’s 23 in December, and he only has 1,100 career ab’s. Controlled through 2030. Walk % continues to go up. Has plus sprint speed.  and I know I’m in the minority. He’s never going to be great at 2nd, but I think he has improved. Still below average, but closer to average. His contact quality needs to improve, as does his baserunning. I believe there is more there vs. what we’ve seen, and I wouldn’t want to move him for what I’d expect they’d get for him. His trade value has never been lower and never will be lower. Selling the first overall pick at his floor, coming off a hamate injury, doesn’t seem ideal to me. I wouldn’t completely rule out a trade though, if he carries more value than I expect he does.

We talked about Henderson above, and the backup catcher above.

So, what about 3rd?

I like Jordan Westburg a lot. The O’s believe he will be ready next Spring.
I’ll be excited to see him back in an O’s uniform.
But after being limited to 85 games in 2025, and missing all of ’26; he’s going to have show he can stay in the lineup.
Even if the O’s are optimistic about Westburg for ’27, you can’t go into the Winter putting his spot down in pen, right?

Blaze Alexander will be back, and he’s an option at 2nd and 3rd.  Ideally he’s your UTI guy, but if you got to Memorial Day and Holliday hasn’t taken a leap, maybe Alexander is taking his playing time?

What if Westburg is generally healthy next Spring, but after the elbow-surgery says 2nd is a better option for him than 3rd?
In that case, I’d still want to come to Spring Training with Holliday still on the roster, and make Westburg prove he was healthy.
If it’s next March, and it’s clear that Westburg can only play 2nd, than maybe you’re more likely to talk me into a Holliday trade.

We mentioned Alexander, and of course have to again mention Mayo.  If Mayo can’t get at-least sometime in RF, than he’s limited to 1st / DH / 3rd.
He’s always going to be below average at 3rd.
If Basallo is DHing for 60-80 games, that factors.
If O’Neill is on the roster, and DHing some, that factors.
Mayo’s production the last few months also has to factor. He’s got four arbitration years left, and he’s got a .754 OPS for the year – having absolutely crushed LHP.

Encarnacion-Strand has done enough over his 160 ab’s with the Orioles to want to see him back in some capacity next year. Particularly with him also crushing LHP.

7. The Offensive Approach

The Orioles are 12th overall in runs scored, 16th in on-base %, and 23rd in slugging.

They haven’t slugged as expected this year, and they’ve scored less than they should have.

For a nearly top 1/3 overall offense, there are too many nights where just can’t get anything going.

The hit the ball harder than most (team exit velocity, hard-hit rate, barrel rate), but they’ve struggled to manufacture runs, and haven’t hit enough homers for an offense that was built around their expected power.

Most of baseball has a three true outcome offensive approach (walk, k, homer).

I know nobody wants talk about batting average in 2026, but being 27th overall in batting average (.234) feels limiting.

8. The Housekeeping

Luis Robert Jr.’s $20 million club option – decline. He played three games and pulled a hamstring. A free lottery ticket in August is a $20 million mistake in November.

Ryan Mountcastle’s $7.5 million club option – decline. Fifteen plate appearances this year.

Leody Taveras in his third arbitration year – non-tender. An 81 wRC+ in 444 plate appearances and an unplayable right-handed side. His final numbers look bad, but will say he gave the O’s a reasonable option a lot of nights this year.

And the thing nobody can fix: Again, O’Neill is owed $16.5 million in 2027 off a 94 wRC+ and a shoulder injury.

9. The Payroll Has To Jump Again

A wish list that doesn’t balance isn’t a plan, so let’s do the math.

Roughly $124 million committed before you sign anyone. At a flat $163 million, that’s $39 million of room.

Plan to take the payroll to approximately $185-$190 million, and that’s $61 to $66M to play with to address the needs identified above.

Payroll again going up after another losing season would be good to see.

I do believe you could build a contender with payroll being flat, or even moving back.
But what a larger payroll should do, is give you further depth, and the ability to get more things wrong / better handle adversity.

Elias

I called for his job in August and took the headline back in September, and I meant both.

Here’s where it actually stands. Rubenstein authorized a franchise-record payroll and got a losing season. Elias then sold at the deadline and got a genuinely strong return – five top-100 prospects in the system now, three of them acquired this summer. The farm is stocked. The books are the cleanest in baseball. Baz and Bradish are signed long-term. Basallo is under contract through 2033 at an average of $8.4 million.

2025 and 2026 have been highly disappointing years for Orioles fans.

I am someone that has largely been an Elias superfan for his tenure, but there can’t be unlimited rope.

If he’s going to be back for 2027, he has to have some conviction about the roster he wants, and he has to figure out to build a contender.

I like positional versatility.
I like having a team that has multiple bites at the apple vs. going all in on any one particular season.

But barring some crazy run here in the last 12 games, the O’s will have not reached October two years in a row.
The mentality for everyone in The Warehouse should be that can’t continue in ’27.

The National League is probably superior to the American League at this point, but the AL East remains the best division in baseball.
The goal should be to build a team that looks like they could win 95 games and the East next year.
The goal shouldn’t be to build a team that looks like they could possibly / maybe sneak into the post-season next year if everything goes right.

You’ve got a deep system, you’ve got an Owner who says he’s committed to spending.
You’ve got an existing roster which has both plenty of questions and plenty of talent.

It’s on Elias to figure out how to make everything work in 2027.