At the Pete Alonso press conference David Rubenstein made even more comments about how the Orioles do not have a limit on what they are willing to spend in order to contend of a World Series.
Comments like this were beginning grow old for the fans after last offseason saw little long term financial commitment but now that the Orioles have flexed their new financial muscles with the Pete Alonso signing it feels like those comments mean something again.
Most immediately it makes you think that there we may see more money spent in free agency in the coming weeks and hopefully that is true. However free agency isn’t the only place a team can spend money.
Ever since Adley Rutschman debuted in 2022 Orioles fans have been patiently waiting to see their young stars extended. Since Rubenstein took over he has made multiple references to how great it was that Orioles fans got to root for Jim Palmer and Cal Ripken Jr. for their entire careers.
In August of this year O’s fans got their first taste of extending a young star when Samuel Basallo signed his 9 year extension. A 67 million dollar extension is small beans compared to some of the extensions we’ve seen other orgs hand out but it was still good to see the front office execute a deal like that. It pointed to a willingness to take on risk and an ability to negotiate that prior to Basallo signing that deal it would have been hard to say for sure that the Orioles had.
I would love to see them build on that extension and the recent signing and extend more of the Orioles young core or even some players that aren’t necessarily considered part of “the young core” so in this blog we’re going to be looking at who can/should the Orioles be trying to extend this offseason.
Trevor Rogers
Out of all the players currently on the roster a Trevor Rogers extension makes the most sense. He’s coming off a career year but he’s never been healthy for a full season. He’s also been open about how coming to the Orioles and working with their staff helped him get back to a version of himself that he didn’t know existed.
So it seems like he’s happy where he is and he should be motivated to capitalize financially on a season that could be difficult to recreate.
From the Orioles side they could use some rotation certainty. When you look at the position player side of the roster there’s a lot of guys that are under team control for 4-6 years. On the pitching side there are not enough starting pitchers under team control to fill out a rotation now let alone 2 seasons from now.
I checked on Roger’s agency to make sure that they’re not going to be a roadblock to an extension. He’s represented by PSI Sports Management who appear to be most known for representing Aaron Judge. Although as you peruse their website (which could use some work in my opinion, use some of that commission from the Judge contract) you’ll see they represent a number of players including old friend Joey Ortiz and new friend Boston Bateman.
In their notable contract section of the website they are promoting 2 contracts I found interesting. Scott Kingery signing the biggest deal before an MLB debut and Trevor Stephan’s pre arb extension with the Guardians.
I think it’s fair to say they’ll be open to negotiating a deal.
So what’s the number?
I tried to find a precedent for signing a pitcher to an arbitration extension who had never made it through an entire season in a 6 year career BECUASE you think that he’s going to be an important part of the rotation. It turns out it’s kind of unprecedented.
Pitchers with those kinds of durability issues sometimes do sign extensions but those are usually small bean extensions that are more about getting a pay raise in arbitration in exchange for another year of control. Drew Rasmussen’s extension from last offseason for example
Trevor Rogers is not looking for the Drew Rasmussen extension.
So there’s not a perfect 1-1 match for Trevor Rogers situationwise but here are some contracts that I think could be instructive. Both of these guys signed their extension around the age of 28 which is right where Trevor Rogers finds himself and similar to Rogers neither of them had a long track record of 160+ innings year after year.
Mitch Keller
5 years 77 million
This contract bought out 2 years of arbitration. It was coming off a career year for Keller. Rogers peaked a good deal higher this past season than Keller did but if you look at Keller’s 2023 baseball savant page next to Rogers 2025 page there’s not a world of difference and the Steamer projections for 2026 and those 2 guys are projected to be nearly identical pitchers next season.
This deal was set up to be a slight raise in arb 2 and then a gradual increase from then on, 15 million in 2025, 16 million in 2026, 18 million in 2027 and finally 20 million in 2028.
I’d be surprised if either Trevor Rogers or the Orioles want to sign a 5 year extension right now. From Rogers’ side if he can perform anywhere near the level he did in 2025 and be pretty healthy over the next few seasons and hit the market again at 31, that would set him up nicely to get another big pay day.
From the Orioles side if 2025 was a major aberration and Rogers is the same injury prone pitcher he’s been for most of his career then 5 years is a long time to be paying a player like that double digit millions.
In general though, something in around 15-20 million AAV for 3-4 years seems like a win-win for both sides.
Pablo Lopez
4 Years 73.5 Million
A fellow former Marlin! Lopez’s extension bought out his last year of arbitration the same as a Trevor Rogers extension would so that is similar. Lopez signed that deal early in the 2023 season and if you look at his body of work from 2020 through 2022 (which includes a Covid shortened season) he made 63 starts at a 3.52 ERA with a 3.48 FIP with a really consistent WHIP, K% and BB% numbers. That was enough for the Twins to feel good about giving him a 4 year 73.5 million dollar extension. He got a small raise in his final year of arbitration and then 21 million AAV for the next three.
If you look at Trevor Rogers body of work over the last 3 seasons it’s not as good. It’s about 100 fewer innings, the WHIP is all over the place year to year and the K% and BB% are worse.
That doesn’t necessarily mean that Rogers will get less. As we’ll see with all these examples Rogers had a better year leading up to this would be extension than Pablo Lopez did leading into his.
This deal was set up so Lopez got a slight raise in his final year of arb and then 21 million per year for the next 3 seasons.
21 million per season for 3 seasons is probably a bit more than the Orioles would like to pay based on Rogers injury history but if you want to convince good players to forgo free agency sometimes you have to go a little above your “ideal” pricepoint.
If Rogers can stay healthy and is even 80% of what he was in 2025 a deal like this would be a steal. There’s just no track record of extended health though and the projections suggest that 2025 will be his only season with a sub 2 ERA so it’s a risk the O’s have to weigh. The good thing is that they know more about his health than anyone else.
73.5 over 4 years isn’t bad and with the lack of payroll the Orioles currently have they could afford to put more of that money on the first year of the deal and spread that 73.5 out a little more evenly so that it plays like the true 18 million AAV. They could even front load it so that by the time it’s time to pay guys like Henderson/Wesburg the Rogers contract isn’t gumming up the payroll.
Bounce back Candidates
This is a group of players that make a lot of sense to extend but they are either coming back from an injury or a down season or a combination of both. It’s a tricky situation to negotiate an extension.
The team sees the talent and the fact that the players’ value is at a low point and thinks they can offer them a less expensive extension because of their injury/underperformance and bet on them bouncing back and that extension being really valuable.
The player feels like if I just have the year I know I can have I can earn a lot more money than this low ball offer I’m getting from the team.
So it’s a balance. If the team wants to actually extend a player in this situation they have to offer enough so that the player chooses to pass up on the opportunity to prove that they are worth more. However if the team pays them based on a predicted bounceback and then the under performance/injuries continue then you’ve got a bad contract.
Adley Rutschman
If you had been present at the 2024 All Star game and had just walked around asking every front office/ media member that you came across what an Adley Rutschman extension would cost the Orioles, they would have told you that he was going to get a record setting contract for a catcher.
Fast forward a year and half of poor play later and now the Orioles have extended a different catcher and Adley’s future with the Orioles is in question.
I’ll start by trying to answer the question: should the Orioles want to extend Adley Rutschman?
The short answer is yes, the long answer should probably get it’s own blog post so I’ll try to thread the needle here.
The argument in favor of extending Adley boils down to the fact that a good defensive catcher who is also a well above average bat is basically a roster building cheat code.
Behold the fWAR leaderboard for catchers. How many of these players are actually valuable on both sides of the ball? The answer is 1. Besides the Mariners every other team pretty much had to decide between good defensive catcher or good offensive catcher. Teams like the Dodgers and the Blue Jays are happy with guys like Will Smith and Alejandro Kirk who are really good at one side and just above average on the other but having someone who is legitimately impactful on both sides is a game changer.
It’s no surprise that when Adley Rutschman joined the Orioles and was clicking offensively they immediately went from the worst team in baseball to among the best and then when his offensive performance dipped they went right back to being bad again. Getting a 126 wRC+ from a plus defensive catcher is good, sorry if that offends.
Now it’s been awhile since Aldey was that guy and I think it is fair to ask is that behind him. I certainly don’t blame people for questioning him but I don’t believe he’s cooked and I actually don’t think hardly anyone thinks so. If you took all of the smartest baseball people and said “You have to put your life savings on 1 of 2 Adley Rutschman season prop bets. Would you rather bet his OPS is over .800 or under .700? I think 9 out of 10 people would bet on Adley to bounce back to his .800 OPS self.
I did this as part of his season report card so you can take a peak there or you can go to Fangraphs yourself and try to see where he fell off. It’s not easy to spot something wrong. His 2025 batted ball metrics were the same if not better than ever, same with his plate discipline/ swing and miss metrics. There is no data besides his triple slash that says he’s washed (I do get how that particular data point is compelling).
A lot of the angst around Adley this offseason is because after his bad second half in 2024 EVERY SINGLE PERSON who had any sort of baseball related platform said that he would bounce back in 2025. Then he didn’t and people really don’t like to be wrong so this time around when Adley comes up you hear a lot more hand wringing and people being like IDK about Adley.
I’m not immune either, I was so confident that in 2025 we’d get the typical Adley season and then when he didn’t come through it made me ask myself what did I get wrong with him? After a healthy amount of clicking around on Fangraphs and Baseball Savant I’m deciding to believe in who Adley has been for his entire life leading up to July of 2024 and I think there is enough data behind backing me up that it’s not a wholly emotional decision.
Besides just performance, now that the Orioles have Samuel Basallo and Pete Alonso locked up for the next 5 years I do think you have to consider roster fit. If you were to extend Adley you’d have 3 guys on long term deals that all need time at DH and I know a lot of GMs really value having that DH spot open so they can have more flexibility. I recognize the roster fit as a real concern.
What makes me interested in extending Rutschman anyway is that he is their only real option as a defensive catcher. As of right now Basallo is not nearly ready to take over a full catcher’s workload and there is some doubt if he will ever be. His bat is legit enough that it’ll be ok if he ends up as a 1B/DH type but if the O’s let Adley loose and then Basallo is just a DH then what? Caden Bodine?
Hearkening back to my earlier blurb on how rare and valuable having a 2 way catcher is I think deciding not to extend Adley because you have Basallo is a real “Waiter my steak is too juicy and my lobster too buttery” situation.
So now I have laid out my case for the Orioles wanting to extend Adley Rutschman, but is this something that could happen?
To start I want to look at his agency and check out the kinds of extensions they’ve done.
Adley is represented by Wasserman. They are one of the biggest talent agencies across multiple sports and other industries and represent a lot of big time players. In part due to the sheer amount of players they represent, they’ve been the ones negotiating some of the biggest arbitration extensions we’ve seen in recent years. Tyler Glasnow, Byron Buxton and Matt Olson to name some of the more prominent ones on their website. So from the agency side I think it’s a go.
If the team should want it and the agency is fine negotiating it then it really comes down to would Adley accept an extension offer?
The answer to that question is always if they offer him the right amount of money. So what is the right amount of money to get an Adley extension done?
As a reference here are the most recent catcher signings/extensions high to low in total value:
Will Smith: 10 years 140 Million
Signed at age 28
Cal Raleigh: 6 years 105 million
Signed at age 28
Sean Murphy: 6 years 73 million
Signed at age 28
Alejandro Kirk: 5 years 58 million
Signed at age 26
Willson Contreras: 5 years 87.5 million
Signed at age 31
JT Realmuto: 5 years 115 million
Signed at age 29
It’s an interesting group. There are some outlier figures but in general the years seem to mostly be about 5-6 and the AAV is in the mid to high teens. I think if you’re the team you’d love to get Adley on the Sean Murphy deal. That would feel like an absolute steal but I just don’t think that number is at all enticing to Rutschman.
2 years ago he and his agents were probably thinking they were going to get double the Will Smith deal and if he bounces back in 2026 he would still be able to easily clear the Sean Murphy contract.
However after a season and half of poor performance I would imagine the Rutschman side has to know that if he’s down again in 2026 that even a great 2027 wouldn’t be enough to erase a 2 and half year stretch of sub par play.
So I’d be interested to know their response if the Orioles approached them ahead of the 2026 season and basically offered them the Cal Raleigh extension and maybe even upped it a little, say 6 years 110 million. You give Adley a slight raise up to 10 million in 2026 and then it’s 20 million per for the next 5. An AAV of 18.5 over his age 28-34 seasons.
With that figure you are giving Adley respect for what he’s shown he can do by offering him as much as Raleigh who has drastically out performed him over the last few seasons. I don’t know how he could turn down that contract based on how the last few seasons have gone. If he signs it and becomes a 4-5 WAR catcher again then you’ve got a valuable contract.
Kyle Bradish
Bradish is in a different situation than Rogers or Rutschman. Last time he was healthy he was one of the very best pitchers in the American League and if he comes back from injury and is that dude for the next 3 seasons before hitting free agency then he’d be looking at a massive payday. I wouldn’t blame him for wanting a chance to prove that he’s that dude.
However Bradish was a 4th round pick whose signing bonus was under 400K. Because of when he missed time his estimated arb number is only 2.8 million this year. Could the fact that Bradish hasn’t gotten his hands on a big contract and at 29 still has 3 more arbitration years before he hits free agency at 32 be motivation enough for him to be interested in extending?
Assuming that Bradish’s answer isn’t check back next year after I drop 170 innings at a sub 3 ERA and an 11 K/9 what would a fair offer look like?
In order for this to be worth anyone’s time we are talking about a 6 extension that buys out 3 years of arb and gives the Orioles 3 additional years of control. Bradish would finish that deal at the age of 35 so you’d have to really make it worth his while because you’re making it so that by the time he hits free agency a mega deal is off the board.
The existing contract that I think you could base this off of would be Logan Webb who signed a 5 years deal that bought out 2 years of arbitration. He basically got 2 raises for the arb years and then 23 million AAV for the next 3 seasons after that. His earnings went 8, 12, 23, 23 and 24 (millions duh).
So a similar Bradish deal would add just one more arb year raise on the front end. It could be something like 5, 10, 15, 25, 25 and 25. That would come out to 6 years 105 million (speaking of Cal Raleigh’s contract lol). I think if you put 100+ million dollars guaranteed in front of someone who’s current career earnings is about 7 million I think he’d have to consider it and it would be a win-win if he did sign it.
As far as his agency goes Bradish is represented by All Bases Covered Management. I did some searching and I could not come up with a website for this agency so IDK if they’re just kicking it old school or Google’s search feature is just cooked.
They do have a LinkedIn page which I now follow and I was able to find some information about the agency on other sites. According to MLB TradeRumors, in the past they’ve represented big names like Lorenzo Cain and Eric Gagne and Spotrac has them listed as the current agency for 7 major leaguers including 2 other Orioles Keegan Akin and Grant Wolfram.
With possibly incomplete picture of who All Bases Covered represents and their track record I don’t think I can say one way or another if they’re likely to faciliate an extension but it would appear that Bradish is their most important client so if you reached out I imagine you’d get their full attention.
Colton Cowser
Cowser is a controversial extension candidate. Unlike the other 3 guys I’ve mentioned so far he has not reached arbitration so this would be a pre-arb deal. The reason he’s controversial by my own admission is that the delta between what his performance in 2024 and his performance in 2025 is pretty large. In 24’ he was a plus defender in left and center and had a wRC+ of 119. That’s a great player! In 25’ he was an ok defender with a wRC+ of 83. That’s a bad player!
Besides the poor performance you also have to consider that you have him for the next 4 seasons which represents the remainder of his 20s and for an outfielder who provides a lot of value with his defense represents most of his prime.
So why would the Orioles want to extend this guy?
There are a couple of reasons.
I believe that there is a logical explanation for Cowser’s performance in 2025. The explanation is broken bones. He broke his hand in the first series of the season. When you break your bones even if you rehab hard and get back as soon as possible that doesn’t mean that there’s not immense discomfort. If you’ve ever broken a bone, think about how that body part felt after 6 weeks. Would you have wanted to play professional sports at that point? How would you have felt facing a Mason Miller fastball? Being a professional athlete doesn’t heal your bones faster, it still hurts!
On top of the broken hand after he came back he broke multiple ribs and then concussed himself. Neither of those things are good for your ability to play baseball.
The other reason is that putting together a major league outfield is difficult and expensive. You look at the teams this offseason who need outfielders and don’t want to hand out a 9 figure contract and the free agent options available to them are a bit depressing. In trades market teams don’t typically trade away healthy 3 WAR outfielders unless you’re willing to overpay for them.
The last 2 offseason the Orioles have spent a lot of resources pursuing corner outfielders in their early thirties. They gave a big deal to Tyler O’Neill and traded a talented pitcher for Taylor Ward and before you know it they’ll be gone and the Orioles will have to spend resources replacing them. How nice would it be to extend Cowser and just not think about one of the 3 outfield spots for the next 6 years?
It wouldn’t be the kind of name your price extension like what I’d be willing to offer Gunnar Henderson but if Cowser and his representation are willing to play ball I think something similar to what Lawrence Butler signed last offseason could work.
The contract Lawrence Butler signed last offseason was a 7 year 65 million dollar deal. He was 24 and it bought out 2 years of pre-arb and 3 years of arbitration. He got a definite raise in the pre arb years and then and then about what you would expect a good outfielder to get in arbitration guaranteed and then the team gets 2 additional years of control and the option for a third at a nice high figure for Butler.
This is a good model for what a Cowser extension could look like. Cowser is a little older and one year further along in his career so maybe instead of 7 years and an option you’re looking at 6 years and an option. If you need to incentivize him you could make it a player option instead of a team option.
That might look like 2.5, 5, 8, 12.5, 15, 18 and then a player option worth about 20 million. Which would come out to 6 years 61 million (7 years 81 million with the option). That would be a good chunk of change for a player to guarantee themselves in their first 8-9 years in the league and he could still hit free agency at 32 at the earliest which is early enough that if he’s a good player then he could get paid again.
For the Orioles this is beneficial because they lock up a productive player who should be able to give you 2-4 WAR per season (if healthy) at an AAV just over ten. At no point is paying 10ish million for average to good corner outfield production going to kill you.
Rental corner outfielders who are not good cost double digit million dollars, why not lock in a fan favorite for his entire prime?
He’s going to play centerfield for a few more years and then in a couple seasons when someone like Enrique Bradfield, or Nate George is ready to take over everyday center field and Tyler O’Neil is off the books he’ll slide to a corner and be a good corner outfield defender for the rest of his career. I’m not worried about him slowing down, his good defense is not based on blazing speed it’s based on getting good reads and having long limbs and that’s not going to change between now and his age 32 season.
I recognize there is downside in Cowser’s profile as a hitter with how much in zone swing and miss he brings to the table but that’s a risk you have to be willing to take. On Cowser’s part I’m sure he feels like he has the upside of being a 30 homer center fielder and if he did that at the right time before free agency he could get mega paid. So it’s a compromise.
Dylan Beavers
Dylan Beavers is brand new to the big leagues so I’m not going to pound the table for an extension. All I’ll say is that I wouldn’t be opposed to the Orioles sending him a copy of the Samuel Basallo extension and saying “we can change the name on this to Dylan Beavers and send it in to the league if you want.” and just see what he says.
Not right now
These are some guys who are on the roster and so could be extended but I don’t think the Orioles need to be looking to do so.
Taylor Ward
The O’s just traded for Taylor Ward and it would be nice to ensure that the return for Grayson Rodriguez was on the Orioles for more than 1 year. However this will be his age 32 season and in order to make it worth his while to forgo free agency now that he’s so close you’d have to offer a bunch of years and I just don’t think that’s necessary. I’m open to them giving him the qualifying offer and trying to re-sign him and if they do great and if they don’t they get a another pick.
Dean Kremer
I really like Dean Kremer and I appreciate what he brings to the table as a reliable 4-5 starter. I don’t think his skill set is one that makes a front office feel like we need to act now and make sure we don’t let him reach free agency. I’m fine letting the next 2 years play out and if they re-sign him after that then cool.
The Boras guys
I have been delaying acknowledging the Boras guys because everyone knows Scott Boras’ reputation.
If a player is represented by Scott Boras you know that they are serious about getting paid what they are owed and are not going to be interested in taking any sort of discount or team friendly deal just so they can get paid a little early or have the pleasure of playing in front of the same fans.
Boras’ signature is making sure his clients get to free agency and get paid the most amount of money possible. He has spoken out numerous times about how he does not think signing an early extension is beneficial to the players. At every step of the way you know that he is advising his clients to turn down extension offers and make it to free agency for the big pay day and he almost always delivers.
If you’re a Scott Boras client you see what he did for Juan Soto and what he has done for many of his clients and think that is what he’s going to do for me. Which is part of why it is so hard to extend a Scott Boras client.
But not impossible. At the end of the day the agent does work for the player.
Over the years there have been Scott Boras clients who have accepted extensions. Just last year Matt Chapman extended with the Giants just weeks before he would have been a free agent. Notably Xander Bogaerts and Stephen Strasberg signed extensions with their teams just a few seasons before they would have reached free agency.
That being said I’m not expecting the Orioles to extend any of the Boras clients on their roster.
What do you think they would have to offer Gunnar Henderson in order for Boras to tell him it’s a good deal? A billion dollars?
He’s not going to advise Westburg to take a deal before he’s managed to play a full season and he’s not going to tell Holliday to sign a deal before he’s had a good season.
I don’t want to be defeatist when it comes to extending Boras clients and I don’t want the Orioles to just give up on extending them either. For the past couple of seasons Boras has said that Mike Elias and the Orioles front office talks to him regularly so that’s at least better than the alternative.
I think the Orioles have the advantage that these young Boras clients seem to enjoy playing together in Baltimore and that with the exception of 2025 they’ve mostly experienced winning with the Orioles. If the Orioles bounce back and Rubenstein puts his money where his mouth is, the Orioles should be contenders to sign these guys even if they follow the Boras playbook all the way to free agency.
The Dishwasher 
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