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Rubenstein: Orioles Hoping For More Extensions With Young Players

By Mark Polishuk | August 24, 2025 at 11:37am CDT

The Orioles officially announced Samuel Basallo’s contract extension at a press conference yesterday, with several players in attendance along with Basallo, GM Mike Elias, and team chairman/CEO David Rubenstein.  Among the many topics addressed was Rubenstein’s desire to make such events a fairly regular occurrence, as the owner showed interest in extending more members of the Orioles’ young core.

“The Orioles’ ownership group is really well capitalized and we have the resources to do these kind of deals,” Rubenstein told Steve Melewski and other reporters.  “It takes two to do deals, but we thought this was a perfect one, for the first one of this type….We have a lot of other talented people on the team who we hope will ultimately want to spend their entire career here or want to spend long-term arrangements with us.  We’re committed to doing more of these as soon as we can.”

Basallo’s deal represents an intriguing turning point for an organization that more or less eschewed long-term extensions for years under previous owner Peter Angelos.  As MLBTR’s Contract Tracker indicates, Adam Jones’ six-year extension from May 2012 was the last long-term extension signed by the Orioles.  Other multi-year deals within the last 13 years were short-term pacts to cover arbitration years, plus there was the unusual circumstance of the three-year extension signed by J.J. Hardy just a few weeks before he was set to hit free agency in the 2014-15 offseason.

Even as the Orioles amassed a wealth of young talent in their recent rebuild, extensions didn’t follow.  This naturally could’ve been a product of the ownership turmoil the organization was going through for much of that period, and Rubenstein’s group only bought the team in early 2024.  It should also be noted that such O’s building blocks as Gunnar Henderson, Jordan Westburg, and Jackson Holliday are all represented by Scott Boras, whose clients have traditionally passed on signing early-career extensions.

Still, it was noteworthy that the Orioles didn’t lock up even any of the non-Boras clients until Basallo (who is repped by CAA) this week.  The fact that the O’s didn’t spend much overall during the first full offseason of Rubenstein’s tenure also created concern amongst Baltimore fans that things weren’t going to change under the new regime, and the discontent only grew when the Orioles stumbled to a losing record after two seasons in the playoffs.

Management can now point to Basallo’s extension as proof that the club is willing to both keep its cornerstone players in place, and to spend the money necessary to make those deals happen.  The catcher’s deal is also an example of how quickly contract talks can escalate, as Elias said negotiations began exactly a week ago, on the same day Basallo was called up from Triple-A to make his MLB debut.

Could more extensions be coming soon?  Henderson didn’t comment on whether or not his camp had already had any talks with the O’s, but expressed a willingness to consider any offer and stated that “the No. 1 thing for me is being on winning teams.”

Henderson’s price tag is about to jump considerably, as the shortstop will enter the first of three arbitration years this coming offseason.  His pro career has already seen Henderson bank a little over $8MM, counting his MLB minimum salaries, his $2.3MM signing bonus from the draft, and roughly $3.4MM from the pre-arbitration bonus pool.  Between this bit of financial security already and escalating arb salaries, Henderson may have already made enough to feel comfortable in betting on himself all the way to free agency, like so many Boras clients.  While the three years of remaining control mean that the Orioles aren’t exactly under the gun to extend Henderson, he’ll only get more expensive the closer he gets to the open market.

Adley Rutschman also declined to comment on any extension talks between his reps at Wasserman and the Orioles, simply telling the Baltimore Banner’s Danielle Allentuck and other reporters today that he was happy to see Basallo rewarded.  The fact that the O’s made such a hefty commitment to a young catcher like Basallo naturally led to speculation about Rutschman’s future, and whether or not Basallo has now supplanted Rutschman as the team’s long-term choice behind the plate.

As one might expect, right now the Orioles believe there’s plenty of room for Rutschman and Basallo to operate in tandem.  Yesterday, interim manager Tony Mansolino told reporters (including Matt Weyrich of the Baltimore Sun) that the O’s could have both players in the lineup in a catcher/DH capacity, or Basallo could play first base.  “The fact that Sammy is so versatile, that’s going to help that a lot…Any time you have two guys that can catch at a high level, on a big league team, you have a massive advantage over teams that don’t,” Mansolino noted.

Rutschman has two arbitration years remaining before he is scheduled to hit free agency following the 2027 season.  As Weyrich notes, extending a player who has had some Major League success is much trickier than extending a player like Basallo right at the start of his career, so locking up Rutschman would represent another spending frontier for the Rubenstein ownership group.  There’s also the question of whether or not the Orioles still view Rutschman as worthy of a long-term investment, considering how his numbers have declined at the plate over the last two seasons.

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Baltimore Orioles Notes Adley Rutschman David Rubenstein Gunnar Henderson Samuel Basallo

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19 Comments

  1. Bartolo Cologne

    3 hours ago

    Good luck. You’re not going to get Henderson, Westburg and Holliday to go for that. They are too established and will get paid handsomely when their time comes.

    4
    Reply
    • Canuckleball

      2 hours ago

      Holliday is established?

      He’s young and still has loads of potential but has yet to get within a stones throw of league average, either at the plate or with the glove. I agree about Westburg and Henderson, but Holliday feels like a guy they at least have a chance of extending. Not saying they will, but there’s a chance.

      5
      Reply
      • Bartolo Cologne

        1 hour ago

        Yes. Holiday has established himself well enough that people know he won’t be a bust.

        1
        Reply
    • bwmiller79

      2 hours ago

      Holliday has a .307 OBP, he keeps that up, he won’t get any money in ARB1 and should consider an extension now.

      Coby Mayo should sign a deal like Basallo if he can get it. I think Mayo is going to be great but he isn’t great yet and he should lock in his money and forget about it and concentrate on hitting the ball.

      Dylan Beavers has looked good, he is a good candidate for an extension but have to give him a look next season. If he hits into July, Id say he could be signed too.

      Id pass on extending Westburg and Henderson and play them both into FA. Rodriguez too, his risk is on tilt.

      Id say Mayo and Beavers and Rogers are the most interesting players on the team.

      Rutschmann and Cowser both failed to improve their stock this season, but a team friendly deal on Cowser would make sense in exchange for a one year team option in ’30, otherwise he can play through ARB too.

      Rutschmann is leveraging his two all star appearances. His ’25 says that he has been downgraded from a strong buy to a hold.

      You’d have to think Rogers is the most important player to the O’s right now and his past struggles could have him open to a team friendly deal. He has struggled with failure and he’ll lock it down if you make a fair offer. Failure can be terrifying. O’s have to get a deal done with Rogers.

      2
      Reply
    • NineChampionships

      51 mins ago

      Only thing Holliday has established is that he has been a flop so far. Not Henry Davis levels of flop but you expect more from a former num 1 overall pick.

      1
      Reply
  2. julyn82001

    3 hours ago

    Good for the O’s. Hope ownership of the also talented young A’s takes the same approach though fans remain skeptical, whether the team plays in Sacramento or Vegas🤨

    2
    Reply
    • CarverAndrews

      2 hours ago

      There is a large Gap between Fisher and any of the more competent owners in the game of baseball.

      2
      Reply
    • NineChampionships

      45 mins ago

      The Rooker extension has worked out nicely but the Butler contract looks like a miss so far. It’s so frustrating to watch him play like those 2 months last year were a mirage.
      Gonna be weird when Bolte/Perez come up and Butler is the 5th best OF on the squad but the only one with a contract.

      I wanna see the FO get ahead on some of these pitchers. Give Morales, Jump, Perkins and Arnold contracts so our starting pitching is set for the next 6+ years.

      Reply
      • Steinbrenner2728

        33 mins ago

        The A’s FO are greenlit to give those pitchers their contracts… For other teams to take on in exchange for prospects in the next 6+ years

        Reply
        • NineChampionships

          28 mins ago

          I can’t wait for this team to move to Vegas so we can get some new fans and hopefully new discussions that don’t constantly devolve into the same old, boring Fisher Fisher greedy greedy slop. Yawn!

          Reply
        • Steinbrenner2728

          15 mins ago

          @NineChampionships it gets repeated cause it’s true LOL same with the fire sales and rebuilding cycles every 5 years with Billy Beane and Bob Melvin to cover for him. Glad to know you’re “for Fisher”.

          1
          Reply
      • bwmiller79

        27 mins ago

        The most difficult part about the extensions with the A’s is that Soderstrom, Langeliers, Wilson and Kurtz all have earned a seat at the table to discuss extensions too. The A’s should extend them all but any potential extension should keep their trade value intact year to year.

        Butler’s salary isn’t prohibitive in anyway, he would still interest teams in a trade and that makes his contract a good one. There are a lot of teams who would like Larry Butler on a 3.5M dollar salary in ’26. Even his 16M in ’31 doesn’t hurt his trade value, was a good sign for the A’s.

        Reply
  3. The_Porcupine

    2 hours ago

    Who else would be cornerstone players to lock up, if not westburg, henderson, and holliday? I dont trust adley. No one else has really developed.

    Reply
    • ba$eba||F@n21

      2 hours ago

      Cowser, Greyson, Kremer, Mountcastle, Bautista, Mullins, Santander – they can/could have all been approached for extensions prior to free agency or trades. I’m not making a case for or against any of them, simply listing other names that would have qualified for extensions.

      Obviously, of the group remaining that I listed, the team would probably prefer to lock up Cowser and potentially Kremer. Greyson and Bautista have serious injury concerns that likely tabled any discussions. You obviously want to get as many of the big 4 – Henderson, Holliday, Westburg and Adley – as possible, I’d say Westburg is the most likely of that group to sign and extension. You have to put some sort of serious offer out there for Henderson and if he decides to pass then you’d want to maximize his value for a haul in a trade – reminds me of the Nationals and Soto situation, it’ll suck but he ultimately made his decision and the organization got a lot of talent in return.

      3
      Reply
  4. jjleavelle

    2 hours ago

    Rogers is probably the next man up for an extension.

    Os need to spend money and invest in legit pitching. They do that, then it shows the core infielders the Os will go out and spend what is necessary to win. No sense in Gunnar or others locking themselves into a long term commitment to an organization that so far proves year after year they are frugal and cut corners on filling out a pitching staff. Hopefully this extension is a sign things are really changing for the Os.

    3
    Reply
  5. The_Porcupine

    2 hours ago

    Sure they could have locked up some on the past. For as much grief as ownership has received for not locking up players in the past, how foolish would have extensions to any of those players you listed look today? Greyso amd bautista are wrecked injury prone. Mountcastle and cedric are on the downturn. Kremer really isnt anuthing special aside from making his starts. I might have been interested in santander given his consistency prior to this year. Cowser, maybe though ill remind everyone hes had only 1/2 a year of good production between the two hes been in the majors.

    1
    Reply
  6. The_Porcupine

    1 hour ago

    Seriously, other than the listed boras clients, who else is core? Cowser? Maybe. I would have thought mayo but hes not proven to be anything but a AAAA player.

    Reply
  7. saj

    56 mins ago

    It was great luck for the Orioles that they didn’t extend their top prospects/young players after the ownership transition two winters ago. Rutschman would have been a big overpay while Rodriguez and Holliday would have been disasters.

    The right thing for a mini market like Baltimore is to copy Tampa and trade em after year 5.

    Reply
  8. Roguesaw2

    2 mins ago

    Mountcastle is old for the group, but from Rubinstein’s perspective he’s young. Perhaps given his recent circumstances he’d entertain a two or three year deal to avoid arbitration.

    If the team is willing to take on some risk, they’ll never get guys like Kjerstad, Bradish or Vance Honeycutt to sign cheaper than they can get them now.

    Same is probably true for Adley. He rebounds to form, his cost sky rockets. The whole “you’re the next Matt Wieters” narrative plays into a more team friendly contract if they were to lock him up.

    Reply

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