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MLB Mailbag: Skenes, Bregman, Nationals, Alcantara

By Tim Dierkes | March 6, 2025 at 10:30pm CDT

This week's mailbag gets into how long Paul Skenes will stay a Pirate, Alex Bregman opt-out scenarios, the NL East favorite, extensions for young Nationals players, potential Sandy Alcantara trade returns, the automated ball-strike system, and much more.

John asks:

I figure the Bucs' cheap owner will trade Skenes before his first arbitration year because he will never pay that kind of salary. If I'm right, when is his final year in Pittsburgh?

After the 2026 season, Paul Skenes will have three years of Major League service time and will be eligible for arbitration.  Barring an extension, Skenes and the Pirates will go through the arbitration process early in 2027, and his salary will take a huge leap that season.

How much of a leap is hard to predict not knowing what numbers Skenes will put up in 2025 and '26.  Remarkably, the first-time arbitration record for a starting pitcher remains Dallas Keuchel's $7.25MM from 2015, though prior to that Tim Lincecum at least topped $10MM as the midpoint between his $13MM filing figure and the Giants' $8MM.  Clayton Kershaw had a midpoint of $8.25MM once as well.  But the first-time starting pitcher arbitration market is not one that moves easily.

Arbitration eligible players are tendered contracts because they offer surplus value to their teams, star players included.  Corbin Burnes, for example, won the NL Cy Young award in 2021 and was paid $6.55MM in 2022, $10.01MM in '23 (after losing a hearing to the Brewers), and $15,637,500 in '24.

A healthy Skenes should be able to top Burnes' $32.2MM in total arbitration earnings, but even $45MM for that three-year period might represent a single season of what he could earn in free agency.

Say Skenes is a 6-WAR type player.  Bob Nutting has owned the Pirates since January 2007; what has happened with this team and similar players since he took over?

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Front Office Originals

Braves Considering Free Agent Catchers
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Guerrero: Asking Price In Extension Talks Was Below $600MM
View Comments (65)
Post a Comment

65 Comments

  1. Fever Pitch Guy

    3 months ago

    Zero chance Bregman doesn’t opt out next offseason if he stays healthy and puts up at least a 4.5 WAR this year.

    2
    Reply
  2. panj341

    3 months ago

    Nutting’s minions will calculate the extra revenue Skenes brings in when he pitches . As soon as this number drops below his arbitration salary the GM will be told to start shopping him.

    2
    Reply
    • RichardJarzynka

      3 months ago

      If a business has a product on which it is losing money, should it keep selling that product?

      4
      Reply
      • avenger65

        3 months ago

        Richard: If Skenes is that product, you have to know whether it’s better for your customers who pay money to enjoy it or if it’s better to sell that product (to the Dodgers, probably) in order to stay solvent. Is it worth being a poor company that no one in your sales area wants to support or is it better to fight for your survival in your chosen profession?

        2
        Reply
        • RichardJarzynka

          3 months ago

          That is ,indeed, the question the business owner must answer.. But in the scenario presented in pnj341’s comment, the company is not being supported by the people in the sales area – even with Skenes.

          1
          Reply
        • LordShade

          3 months ago

          Hmm, I wonder why that is? Probably because the owner doesn’t spend any money on it. Strange how that works.

          1
          Reply
      • JackStrawb

        3 months ago

        Depends on the product, on the people served, on the working people involved… unless we take the fundamentally psychopathic perspective that the only thing that matters is profit.

        Really, the only economic system that makes any sense puts working people in charge of

        1. What is produced.
        2. How much is produced.
        3. Where it’s produced.
        4. What’s done with the profits.

        Reply
      • YourDreamGM

        3 months ago

        Pirates will attempt to extend Skenes for a fair contract. Only if he rejects will he be traded. Not because of $ but because of the huge return of prospects. There no thinking. It’s extend or be traded.

        Reply
  3. RichardJarzynka

    3 months ago

    Bob Nutting, owner of the Pirates, has demonstrated that he WILL spend the money necessary to sign his best players to contract extensions.

    He has, over the past three seasons, given long-term extensions to Bryan Reynolds, Oneil Cruz, and Mitch Keller.

    In the past, he has extended Andrew McCutchen, Starling Marte, Francisco Liriano, Josh Harrison, Francisco Cervelli, and Gregory Polanco.

    Based upon the $10.15 million, one-year contract that Cy Young Award winner Tarik Skubal signed to avoid arbitration, a reasonable extension for Skenes would be 8 years for $140 million with two $30 Million team options. That would bring the total value to $200 Million and keep Skenes in Pittsburgh for the next ten years.

    Reply
    • 66TheNumberOfTheBest

      3 months ago

      You’re about $300 million light there.

      9
      Reply
      • RichardJarzynka

        3 months ago

        Skenes might be paid $300 million more as a free agent, but free agency is 5 seasons away and for the next two years he will be making near the league minimum.

        The incentive for him to sign the extension I suggested above is to start making much bigger money now. As I wrote, Cy Young winner Tarik Skubal signed a one-year, $1o million contract to avoid arbitration. So, I propose giving Skenes $10 million this year, which is a raise for him of more than $9 Million. Then, increase every year for the following 7 seasons.to a high in the last year of about $25 million. Then, team options at $30 million .

        That protects Skenes earnings against injury or subpar performance and enables him to start making big money sooner.

        Reply
        • DroppedThirdStrike

          3 months ago

          He might sell his arb years and a single free agent season but nothing beyond that.

          He’s a generational talent and, barring injury, he’ll be paid like it. If he performs as projected he will be net the highest ever FA contract for a pitcher. By a lot

          2
          Reply
        • Tom

          3 months ago

          As a 1/1 pick, Skenes also already banked $9M±…doubt he’s willing to sell multiple free agent years at a lower cost like a lot of players without huge bonuses do.

          3
          Reply
        • avenger65

          3 months ago

          Tom: I’d sign him to a big extension if he would just smile. He didn’t even smile when he won Rookie of the Year.

          1
          Reply
        • straightuphonestguy

          3 months ago

          You’re targeting somewhere between Yamamoto’s 12/$325M and Cole’s 9/$324M in terms of AAV. Maybe the Pirates could buy out a max of 2 FA years. I think 7/$230M could get the conversation started. It replaces two years of league minimum and cost-controls his arbitration for his age-28 and 29 seasons. It’s hard for me to guess his arbitration numbers, but let’s aggressively call it $50M for all five years. This would value his two FA years at roughly $90M each. It’s a princely sum, but the difference is that if he goes year-to-year, he’s going to be the first $400M+ pitcher if he remains relatively injury-free at 27 years old.

          Reply
        • JackStrawb

          3 months ago

          $2/180m? Anything’s possible, but that seems hugely unlikely, particularly five years out from his age 28-29 seasons. The Pirates certainly won’t be going anywhere near that.

          1
          Reply
        • YourDreamGM

          3 months ago

          7 years 120 million. You already have him for 5 years 44 to 50 million. You get 2 free agency years at about 30m each. He is set for life no matter what happens and gets to hit free agency for mega pay day.

          Pirates would gladly do this contract. It’s all up to Skenes. Does he want more $ than he could ever spend guarantee? Or take the risk of keeping alive and healthy for the next 3 4 5 years?

          Maybe you give Skenes a taste of winning this year and go 15 years 400 500 million. Looking iffy on winning and come on it’s Bob Nutting. Guy doesn’t take any serious risk.

          1
          Reply
        • straightuphonestguy

          3 months ago

          @Jack — No one is paying $90M AAV for Skenes in a vacuum, but these would be the most valuable years he’d be forgoing in an extension versus hitting FA and bundling them with his decline years on a long-term contract. It’s a tricky spot for Pittsburgh because you can go year-to-year through 2029 instead for about 1/5th the cost. The only way to tamp down would be to offer some opt-outs, but given they have five years of control over him already, it wouldn’t really make sense to put the opt-out until the FA years which are exactly what they’re trying to purchase by overpaying years 2-6 (pre-arb + arb). Rock and a hard place. To be honest, I’d never feel comfortable going more than a half-decade on a pitcher, even one of Skenes’ caliber, so I couldn’t even fault Pittsburgh for being gunshy here.

          @Dream — I don’t think Skenes would sacrifice 2 prime FA years for $30M each.. maybe I’m wrong. He’s already pocketed a fat signing bonus, so I feel his risk tolerance will be much higher. Granted, he’d still be young enough in 2030/31 for a mega contract, but he could easily top Cole’s AAV and guarantee in 29. Maybe I was overaggressive with the AAV and Pirates could get him to bite on a 7/$190M (30/31 valued at roughly $70M a piece) tomorrow. That’d still put him in position for an 8/$300M+ in the 31-32 offseason.

          Reply
        • YourDreamGM

          3 months ago

          ,@straightuphonestguy 70m is crazy high and the moon for Nutting. Pirates wouldn’t and couldn’t do it. It would be under 40m. 7 120 130 140 tops. That signing bonus isn’t that fat. Taxes. Agent cut. He ain’t hurting and will get endorsements as well. But it’s not 120 million. It’s up to you. A career hurting injury isn’t super likely. A car accident or freak medical illness even less likely. But here’s 120m no matter what. It’s not just 30m a year it’s 120m. Accident or blood clot do you think Nutting is going to be a nice guy and pay what he would have received in free agency? Pirates payroll 85m. How they going to pay Skenes 70m? But they’ll have Reynolds Keller off books so 30 40 doable.

          1
          Reply
        • straightuphonestguy

          3 months ago

          It’ll be interesting to see how it plays out, that’s for sure. I think the prudent move will be to trade him 27-28 offseason for a haul. It’s what I’d want my team to do anyway. Pitchers are just so damn risky for the very slim chance he’s the next Verlander/Scherzer/Clemens/Johnson type. Also, maybe an extension makes more sense once he into arbitration. It would be a bigger guarantee, but the team gets to pocket 2 more years of the league minimum.

          1
          Reply
        • YourDreamGM

          3 months ago

          @straightuphonestguy Extend or trade. Either works. If they extend him he can still be traded just a few years later right? Likely traded 1 year or 1 year 2 months left.

          No idea what will happen. It’s entirely up to Skeenes. Pirates should be happy to pay his arbitration and give him 2 more years at 30 35 million a piece. It will cost Skenes tens of millions but not hundreds of millions. He has to think of it as insurance.

          It can gradually go up. Give him 3 or 4 million this year and 6 or 7 next. It’s better than 800 grand or million and even Pirates can and should be willing to afford it.

          1
          Reply
    • JackStrawb

      3 months ago

      @RichardJarzynka Seems light, but not as light as some are making it out to be, though the two blanket, consecutive team options with no buyouts are extremely favorable to the team.

      Say that with 5 years of team control left his *reasonable* upside is $50m for 2024-2029, his age 23 to 28 seasons. You’re then suggesting a 3/90m guarantee from 2030 to 2032, his age 29-31 seasons, followed by two team options at 30m each for 2033 and 2034, his age 32-33 seasons.

      That’s $140m guaranteed, maxing out at $200m if both team options are exercised.

      That deal gets the entire heart of Skenes’ career and doesn’t even offer buyouts in 2033 or 2034, for a pitcher with, IF healthy (make that IF bigger), more upside than anyone in the game.

      If Skenes instead chose to reach FA at 29 in 2030 where he averages 90% of his 2024 performance from 2025 to 2029, he’d be in line for something like 10/$400m plus the $50m he would have made while under team control, totaling $450m, where by contrast you’re pitching 10/$200m that leaves him entering FA for the first time at age 34.

      Can Skenes make up that difference of $250m from age 34 on? If he’s been Zack Wheeler he can probably add another $150m to his career earnings, but it’s hard to see him making $250m from 34 to the end of his career.

      At the same time, the key point is health. How much is the $140m guarantee worth, that keeps him in caviar until 2100 A.D. for giving up perhaps $100m by forgoing FA at 29?

      Seems like he’d want a higher guarantee, one that can be satisfied with buyouts and with lavish vesting options, where the team might obtain the reverse by including the clause Jon Lester signed with the Red Sox, where a 1/$1m year is added to his deal if he misses a year due to TJS.

      This is a tough one. A team like the Pirates will be wrecked if they sign Skenes for an average of $30m from 2027 to 2032 and he can’t provide any kind of return for that money.

      1
      Reply
      • JackStrawb

        3 months ago

        Ah, misread his age. He’ll be a FA at age 28 rather than 29, in fact a very large difference, as much as $50m, possibly even 60m if he’s chugging along with something like a 6 WAR peak his last controlled year.

        1
        Reply
      • GASoxFan

        3 months ago

        All these numbers ignore one key issue in mlb…. *wage inflation*

        If mookie Betts post-arb FA happened today, he’d be looking at 180-200% of what he signed with the dodgers for. And that’s as far behind us as skenes FA is ahead of us. Devers would be asking more than his deal too, probably in the 450 range which is 50% more than just a couple years ago.

        The idea that skenes wouldn’t be looking for more than today’s prices 5+ years out is leaving part of the equation aside.

        Any team extension doesn’t just give cost certainty or buy a couple free agent years, it’s a hedge against wage inflation too.

        I’d guess 7/155-160 is probably a fair starting point.

        Reply
    • Never Remember

      3 months ago

      Is this you Bob?

      Reply
  4. 66TheNumberOfTheBest

    3 months ago

    Skenes could blow out his arm and miss the rest of his Pirate tenure and despite this reality they made absolutely ZERO effort to improve the team this winter.

    The Pirates should just trade him now for the biggest return in MLB history and hope it turns into the baseball version of the Herschel Walker deal. Maybe they could pool enough young cheap good players together to actually compete and maybe possibly hope to win.

    Instead, they’ll just slog along and pinch pennies until they squander the gift that fell into their laps and do nothing.

    Reply
    • letitbelowenstein

      3 months ago

      That’s why, were I a GM, my teams would always finish under .500. Committing to pitchers these days is too big a risk. No way I would sign a pitcher, regardless of how great he is, to a 7, 8, 9-year deal. I doubt I’d even go 5 these days. Sign a pitcher for five years and, if you’re lucky, get half of that in return? Pass.

      1
      Reply
      • Tom

        3 months ago

        Do you have any idea how much money teams make in playoff revenue? Even one series has shown to be a ridiculous amount of money. Spending some money, even if it goes wrong, is probably a better bet than just finishing under .500 all the time because a team is scared of what could happen.

        2
        Reply
    • TheMan 3

      3 months ago

      I don’t trust Cherington enough to obtain good players in return for Skenes.

      2
      Reply
      • 66TheNumberOfTheBest

        3 months ago

        Why would you?

        I wonder if anyone wants to reevaluate just how amazing what Huntingdon did here was with the context of how little Cherington has managed to achieve in the same chair.

        2
        Reply
    • Rsox

      3 months ago

      What did they need that they didn’t go out and get though? Keeping in mind that the Juan Soto’s and Corbin Burnes’ were never going to happen (Sasaki either), who should they have signed that would improve the team?

      Reply
      • 66TheNumberOfTheBest

        3 months ago

        They possibly upgraded at first but could have gone bigger.

        They could have upgraded at 2B, they got Adam Frazier instead. Same in the OF, got Pham.

        Who is their SS? Do they have a plan if Cruz and Hayes are bad again?

        Getting even average players at some of these spots could have given the pitching staff a chance.

        3
        Reply
        • RichardJarzynka

          3 months ago

          Who, specifically, should they have signed?

          Cruz was not “bad” last year. He had a 3.5 WAR. That’s very good.

          Adam Frazier is NOT their starting 2B. That is Nick Gonzales, who is a league average second baseman.

          Pham is NOT an “upgrade.” But he’s little worse than Michael Conforto who got a ridiculous $17 million for one year from the Dodgers.

          1
          Reply
        • 66TheNumberOfTheBest

          3 months ago

          A) I’m not here to do their pro scouting. Are you trying to claim there were NOT better players available?

          B) It’s a moot point now.

          C) If you are happy with their roster, I am happy for you.

          2
          Reply
        • Rsox

          3 months ago

          So just comolain they “made absolute zero effort to improve” yet offer no suggestions what they could have done better?

          Reply
        • YourDreamGM

          3 months ago

          I do the pro scouting. Zero 2b available better than Gonzales. 1 ss which would have been an expensive bad contract.

          It takes 30 seconds to do pro scouting. Look at 2b list and see it’s nothing but old trash.

          1
          Reply
        • 66TheNumberOfTheBest

          3 months ago

          If you think they did well, you are free to think that.

          Reply
        • 66TheNumberOfTheBest

          3 months ago

          OK, sounds like they are ready to deliver Pirate baseball for their deserving fans, then, right?

          Enjoy.

          Reply
        • YourDreamGM

          3 months ago

          Looking like another year of Pirates baseball. That’s for sure.

          Not many people are saying they did well. They just took 30 seconds to look at the free agent list and realize there was little to nothing there.

          You are just flapping your gums saying Nutting should spend $ he doesn’t have to get free agents who don’t exist. And of course he has $ he just isn’t not going to take a profit and last I heard he isn’t the only owner just the chairman so it’s not up to him. You don’t have to have 51 percent or greater to be chairman. I never heard what percentage he actually owns. He has to own 20 or 30 percent minimum but after that no idea.

          Reply
        • 66TheNumberOfTheBest

          3 months ago

          OK, as long as you believe in your heart of hearts that Frazier and Pham were the best they could do, enjoy.

          1
          Reply
        • YourDreamGM

          3 months ago

          We like our internal options

          Reply
      • Formerly Depressed Mets Fan

        3 months ago

        As i’m not a pirates fan, im sure u will get more in depth answers then this but generally speaking this team needs more offense. Out Field generally, there were other non-Juan Soto options that would make their OF better in FA. They added a prospect who has yet to prove it at the ML level at 1B, who is now hurt and a 36 year old journeyman OF who has not been an everyday player in years.

        3
        Reply
    • JackStrawb

      3 months ago

      From a typical GM heading up a contender they should be able to get significantly more than what the Red Sox dealt for Crochet.

      If the Mets that would be AT LEAST the equivalent of the Mets top 5 prospects including Sproat.

      Crazy. Wonder if the Mets would do it?
      Would the Pirates? It’s a huge gamble, both ways.
      It wouldn’t make a lot of sense for the Pirates not to get as close to a sure thing as they can, a top 10 MLB prospect, perhaps a top 5 or top 3 along with other top 100 prospects, where the acquiring team brings in a third team as necessary.

      1
      Reply
      • JackStrawb

        3 months ago

        Skenes at the moment is fundamentally untradeable.

        Never mind the cost to an acquiring team’s future seasons of completely gutting your farm system for one pitcher, the Pirates can’t trade him except on the assumption that he’s going to continue to be one of the best pitchers in the game, as teams don’t sell other than high when a player is putting up peak seasons, unless they want their GM chased and egged whenever he’s in public for the next decade.

        At the same time, can a contender bet its present and future on the rotator cuff of a 22 year old?

        The only team I can juuust see doing this is the Dodgers, but how much sense does it make to add yet another ace? They wouldn’t be adding Skenes, they’d be adding the difference between Skenes and their 3rd or 4th starter in the postseason—meaning the improvement is a lot less for the Dodgers than it is for a team like the Mets, though it doesn’t make sense for the current Mets and their very ordinary farm system.

        Skenes improves their chances of making the postseason and winning the World Series, but only from 3-4% to something like 7-8%, while the cost in future seasons of a gutted farm system needing 5 years to recover is huge..

        1
        Reply
  5. Mjm117

    3 months ago

    That Sandy trade haul for the Marlins at the deadline will be _______ ?

    I say underwhelming.

    Reply
    • paddyo furnichuh

      3 months ago

      Noah Miller and Jarred Karros

      Reply
      • Mjm117

        3 months ago

        A career .600+ OPS hitter with no power in the minors plus a possible back starter/ loogy.

        Underwhelming indeed.

        Reply
    • JackStrawb

      3 months ago

      @Mjm117 I don’t think so. 3/55m is left on his deal with the further plus that the acquiring team can bail on the last year, $21m, for just a $2m buyout.

      If Sandy’s chugging along pretty much as before, putting up the average of his 2021, 2022, 2023 seasons, heading for 205 IP with a FIP around 3.50, he’ll be treated like the #1 he’d be, and with two and a half years left on his contract.

      He’ll bring a lot, in that case. Health, though, is everything, and how quickly he can return to form—if he can. And if he’s wobbly the Marlins should be smart enough to know to hold onto him and see if he can’t regain his prior form.

      Reply
  6. FOmeOLS

    3 months ago

    Tim,I don’t know if you read these comments, but I enjoyed this mailbag immensely, especially the mention of Caleb Joseph, whose #36 is on the only jersey I own.

    Here’s a fervent prayer the Evil Empire doesn’t trade for Alcantara, though. That would not be good for the Baltimore boys..

    1
    Reply
  7. hoof hearted

    3 months ago

    Wow, only 1 year under his his belt and their talking about his exit?

    Reply
    • TheMan 3

      3 months ago

      if you read the article, Gerrit Cole had 2 years left before free agency and the Pirates traded him to Houston
      This management team is predictable. They will undoubtedly trade Skenes at his highest value unless a miracle occurs and they give him an extension

      1
      Reply
      • panj341

        3 months ago

        And the only decent player they received in return was Musgrove. I don’t expect Cherington to even beat that return.
        Pirates didn’t even say no when Kyle Tucker was not in the deal.

        Reply
      • JackStrawb

        3 months ago

        And if you read the article for comprehension, this is a full FIVE years left before Skenes’ free agency.

        As for a username such as “The Man” followed by a number, the internal contradiction is amusing, so thanks for that.

        Reply
      • YourDreamGM

        3 months ago

        His highest value is today. Unless you want to live in past his highest value was in June after showing enough to start all star game. They won’t be trading Skenes today. I will guarantee it.

        1
        Reply
  8. Formerly Depressed Mets Fan

    3 months ago

    Love the discussion on how the catching spot could change with the new ball/strike system. As a Mets fan the grew up watching Piazza crush baseballs, i would not be opposed to more offensive minded catchers.

    1
    Reply
  9. somebodynew

    3 months ago

    What if somebody bought the bucs, and they resigned skenes 9 years 860million

    1
    Reply
    • YourDreamGM

      3 months ago

      Anyone stupid enough to give Skenes that contract is making $8 a hour and could never afford to buy a baseball team.

      Reply
  10. dejota

    3 months ago

    “The Astros have a CBT payroll of about $237MM right now. I always find it odd when a team seems willing to have a notably higher payroll or cross a CBT threshold, but only for one specific player. If you had $26MM for Alex Bregman, why not spend that on other players given how crucial each win is?”

    I know your asking why a specific player makes a difference but this is exactly what I refer to when I say owners are pocketing millions more while crying poor. You’re right Crane could afford to pay that money to anybody if it was about wins and he would empower his GM to make the best choice. But it’s not about winning and I wish the media would be more critical of these clear hypocrisys in baseball. This is what I mean when I say all owner lie about revenues. Its obvious if you back in Forbes variations with traditional company evaluations. Also why would any billionaire spend a significant portion of their worth to LOSE millions owning a sports team? They wouldnt and even if you think they owe the public nothing pushing for greater transparency would benefit the sport you guys cover.

    Reply
  11. joew

    3 months ago

    If the pirates are above .500 and Paul is still performing well I doubt he gets traded his first arb year.

    Pirates have a fair shot at being .500 next year. I’d say closer than 2024. I’m skeptically optimistic and has fewer “ifs” than in recent seasons.

    I think the owners could be talked into spending for a generational player so I wouldn’t rule out a real attempt at extending him for either a few extra years or a career type contract with lots of deferrals and perks.

    1
    Reply
    • YourDreamGM

      3 months ago

      Will be traded between arb 2 and 3. Or between year 1 and 2 of extension.

      Reply
  12. The Saber-toothed Superfife

    3 months ago

    Pitch challenge is a dumb idea. Seems silly. It’s part of baseball – right or wrong – things you have no control over and have to accept…..

    It’s a conspiracy
    Trying ruin baseball.

    Reply
    • straightuphonestguy

      3 months ago

      Conceptually, I like the pitch challenge. I have yet to see it in a game, but 2 challenges seem a little light for 9+ innings. I do think it adds an interesting wrinkle that the batter and battery are the only ones who can request the challenge — will make for some good team strategy executed on an individual level.

      Reply
      • The Saber-toothed Superfife

        3 months ago

        In use in the minor leagues. To me, it feels unsportsmanlike.
        Besides it’s kinda lime showing up the umpire. Neutering the game.

        Reply
  13. bcjd

    3 months ago

    I’m surprised the team released a PR photo of Skenes without clearing up that acne. It’s refreshing to see honest images from a firm marketing a product.

    Reply
  14. energel

    3 months ago

    Can anyone tell me what the article said abt Paul Skenes? I do not have a subscription

    Reply

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