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Pirates GM Ben Cherington’s Contract Runs Through 2027

By Anthony Franco and AJ Eustace | September 25, 2025 at 8:50pm CDT

Pirates GM Ben Cherington’s contract runs through the 2027 season, according to Ken Rosenthal of the Athletic. Cherington has been at the helm of Pittsburgh’s front office since November 2019. John Perrotto of The Associated Press wrote last week that Cherington was signed beyond this season, though it was previously unknown if his contract ran through 2026 or ’27. This latest update gives him at least two more years worth of guaranteed salary.

Dating back to Cherington’s first season at the helm – the COVID-shortened 2020 season – the Pirates have a record of 363-504 and have finished 4th or 5th in the NL Central in every season. The club’s last winning season was in 2018 under then-GM Neal Huntington. They lost 93 games the following season. Owner Bob Nutting fired Huntington and brought in Cherington after the following season, even though Huntington had multiple years remaining on his contract at the time.

That same offseason saw the Bucs fire manager Clint Hurdle, whom they replaced with Derek Shelton. Pittsburgh stuck with the Cherington-Shelton pairing for five full seasons, maxing out with 76-86 seasons in both 2023 and ’24. A 12-26 start to year six led them to fire Shelton in early May. They’ve been better under interim skipper Don Kelly, yet their 57-64 record in that time has them playing at the same 76-win pace of the previous two seasons. Some growing pains are always expected at the beginning of a rebuild, but the record has plateaued even as the Bucs have put together a talented collection of young arms.

Under Cherington, Pittsburgh has had much more success drafting and developing pitching than they’ve had on the position player side. The Pirates drafted Paul Skenes No. 1 overall in 2023, and the righty is now the favorite to win the NL Cy Young Award. He gives the club their first bona fide ace since Gerrit Cole and should anchor the rotation for the next few years.

Braxton Ashcraft and Mike Burrows were drafted before Cherington’s arrival but have developed into promising pitchers this season. Closer Dennis Santana has broken out since being claimed off waivers last June. There’s more pitching talent in the pipeline. Five of MLB.com’s Top 100 prospects are in the Pirates organization, and two of them – RHP Bubba Chandler (No. 7) and LHP Hunter Barco (No. 82) – have recently made their big-league debuts. They added another potential impact arm with RHP Seth Hernandez, the sixth overall pick this summer.

Impressive as the pitching group has been, they’ve had too many misses on offense. Henry Davis, the first overall pick in 2021, is a career .178/.260/.288 hitter. Nick Gonzales, selected seventh overall in 2020, has a .259/.302/.378 line in more than 900 plate appearances. While it’s too early to close the book on 2022 fourth overall pick Termarr Johnson, he’s not as highly regarded as he was at draft time because of questions about his power ceiling and defense at second base.

Last year’s first-round pick looks much more successful. Konnor Griffin, the #9 pick in 2024, had a phenomenal minor league season. He’s a potential franchise shortstop and arguably the #1 prospect in the game. Griffin has a chance to become the dynamic position player talent that the club has lacked, but they’ll need a lot more production throughout the lineup. Spencer Horwitz and Joey Bart are their only two hitters who have been even slightly above-average at the plate this season, as measured by wRC+. No team has scored fewer runs.

Cherington said over the weekend that he hasn’t received any indication from ownership that he won’t remain in the position going into 2026. If that proves to be the case, he’ll first need to decide whether to retain Kelly as the permanent manager. The focus will again be on building even a league average offense. Skenes, Chandler, and Mitch Keller form a strong front of the rotation, with all three under control through at least 2028. The team’s payroll annually ranks in the bottom 10 of the league, likely leaving the front office looking in the third or fourth tiers of free agency to acquire some complementary pieces to strengthen the lineup in hopes of getting above .500 and challenging for a Wild Card spot.

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82 Comments

  1. Sparky1000

    1 month ago

    This is an outrage! The Pirates are never going to reach the playoffs with Cherington and Nutting still around.

    6
    Reply
    • 920falcon

      1 month ago

      Nutting will be around for as long as he wants to be.

      1
      Reply
    • James123

      1 month ago

      the pirates ownership needs to make clear which direction they are going. Right now the goal seems to be trotting out a 75 win team as often as possible. So they are playing to avoid 100 loss seasons.

      On the flip side, they can (with their budger) take a big swing every few years. Griffin is their next star- so who cares if Bart is a ok, deal him for a prospect 2 years out to suppor Griffin. Go on all in for a window in a few years.

      1
      Reply
    • LordD99

      1 month ago

      The issue is Nutting.

      2
      Reply
  2. walls17

    1 month ago

    My belief has always been that Cherington must be the lowest paid GM in the league and that’s the only reason why he’s still there

    5
    Reply
    • TJECK109

      1 month ago

      Or Nutting knows there isn’t a line of qualified candidates that want this job

      Reply
  3. Blah blah blah

    1 month ago

    The losses will continue until morale improves

    4
    Reply
    • grizzled sports vet

      1 month ago

      Nice take on the original

      Reply
  4. websoulsurfer

    1 month ago

    People seem to forget that a GM/POBO’s primary job is to make the owner money.

    Apparently, Nutting is making money hand over fist because he has kept Cherington on the job while the team has continued to lose and lose bad.

    During Cherington’s tenure including 2025 the Pirates have not finished better than 4th place in the central, have 4 last place finishes, have a .418 win %, and have not had a winning season.

    4
    Reply
  5. sad tormented neglected mariners fan

    1 month ago

    I know it’s hard for him to win with nutting giving him zero payroll but in the years he’s been at the helm, he hasn’t found a way to make the front office run on no money

    Cleveland, Milwaukee, Tampa, etc all find ways to win but cherington isnt smart enough to do the same

    12
    Reply
    • bigdaddyk

      1 month ago

      Exactly he was given 30 million to spend on free agents and decided to sign 5 non impact players

      1
      Reply
      • greatwhiteangus

        1 month ago

        It’s because the good players available want more than ONE year deals. That’s the issue. Bob doesn’t want to be tied down.

        Look at all the predictions this past off season, many outlets having the Bucs signing Tyler O’Neill to a 3 year deal. It’s like they forgot who the owner of the Bucs is for a minute.

        1
        Reply
    • mlb1225

      1 month ago

      Keep in mind that in terms of fWAR, Joey Bart and Jack Suwinski are his most productive players he has acquired himself (either through draft, trade, etc.).

      3
      Reply
      • sad tormented neglected mariners fan

        1 month ago

        Don’t forget mccutchen but he has acquired literally no offense year in and year out

        I’d argue that if the pirates didnt get Paul skenes there’s a chance he would’ve been fired by now

        4
        Reply
        • AI GM

          1 month ago

          Hard to see Nutting firing him with 2 years left let alone 3 or more. He did fire previous management with years left but they were even worse than Cherington.

          Reply
        • TheMan 3

          1 month ago

          Except that Cutch is third on this team in runs batted in and has drawn the most walks.
          You can blame him to your heart’s content but he would have scored more runs if the players behind him didn’t strike out so much

          Reply
        • mlb1225

          1 month ago

          It’s 2025, we all know at this point RBI is more driven by opportunities with men on base than it is by actual production a lot of the time. He’s only batting .240/.333/.388 with runners on base this year. A .721 OPS with men on isn’t a particularly outstanding clutch performance.

          He has a .665 OPS and 95 OPS+. I love Cutch and I’m going to miss him when he decides to hang it up, but this is by far his worst season at the plate and acting like he wasn’t part of the problem is actively ignoring his actual production.

          That being said, I think he’d play better in a deeper line-up. He gets walk a lot with men on base because there’s no reason to pitch to him when the rest of the line-up is poor. He still has a .346 xwOBA, and both his exit velocity and barrel rate are still around league average. He also is in the 92nd percentile of chase rate.

          Reply
        • greatwhiteangus

          1 month ago

          Cutch’s OPS is higher than 665, it’s just under 700, and this season is pretty much identical to his 2022 with Milwaukee

          We all love Cutch, but it’s time to put BRey at DH and offer Cutch a part time bench gig or we look elsewhere.

          Reply
        • mlb1225

          1 month ago

          My mistake, it’s .699. Either way, I’m okay brining him back for a part-time role, but Reynolds should see more time at DH next year.

          Reply
  6. Jgwi2az

    1 month ago

    Forgot to mention Oneil Cruz is a disappointment too.

    2
    Reply
    • just_another_pretty_face

      1 month ago

      What are you talking about he hits home runs far and fast (all 20 or so of em) isn’t that all that matters?

      Reply
      • TheMan 3

        1 month ago

        Cruz is only batting near the Mendoza line and has struck out 173 times

        1
        Reply
        • greatwhiteangus

          1 month ago

          You couldn’t tell that was sarcasm???

          Reply
  7. panj341

    1 month ago

    He can still be fired at anytime so there is always hope.

    1
    Reply
    • bucsfan0004

      1 month ago

      Cheringron can’t possibly be making more than $5M over the next two years. That’s what he signed Heaney for. Just fire him…. it will be a sunk cost, just like Heaney. If nothing else, it will boost morale within the fan base; Bottom Dollar Bob has to realize this by now

      2
      Reply
  8. Dorkus Malorkus (3768902)

    1 month ago

    I can almost hear Bob Nutting sounding like a penny pinching dad:

    “We are not buying a new GM. We have a perfectly fine one already, and its only a couple years old!”

    2
    Reply
  9. SweetBabyRayKingsThickThighs

    1 month ago

    Gonna need a lot of fireworks and bobbleheads to get people out when Skenes isn’t pitching.

    2
    Reply
    • AI GM

      1 month ago

      Skenes old news. They came out early 2024 for him. By late 2024 they didn’t really care. Sure if you are going to buy a random ticket might as well see Skenes but it’s not a drastic attendance boost.

      Reply
      • greatwhiteangus

        1 month ago

        Agreed. The fans came out for the fireworks not so much Skenes.

        1
        Reply
    • bucsfan0004

      1 month ago

      FYI: there’s only about 9k in the stands on nights when Skenes pitches. I’m sure there’s an occasional weekend start which draws maybe 15-20k, but most home starts… 9k, maybe less

      Reply
  10. mlb1225

    1 month ago

    Okay.

    Reply
  11. mlb1225

    1 month ago

    Bob Nutting, you absolute buffon, if you see this as a reason to bring him back, so help me god. For the love of everything holy in this world, just make one right decision.

    2
    Reply
    • mlb1225

      1 month ago

      There are a lot more, harsher words I would like to use right now that would likely get my account banned.

      5
      Reply
      • AI GM

        1 month ago

        It is reason to bring him back. He should be making minimum 3m but maybe it’s 4. That’s 6 to 8 million that would be thrown away. If you allow the new gm to hire a new manager that will be another 3 to 12 million probably well north of 3. Would fans take it well hiring some no name bargain basement manager?

        If you want rid of Cherington you probably want rid of Williams as well. He should make more than Cherington and may have a extra year or 2 or 3. You add all this up and it’s a lot of $. $ that could be used for extension or free agents. In a year attendance went down significantly.

        Lockout coming soon so if I am Nutting I am not firing Cherington Williams. They should be but it doesn’t make sense. He made his bed extending them all so has to ride it out.

        1
        Reply
      • bucsfan0004

        1 month ago

        The mods are midwest Cubs fans… i’m sure they don’t care if you rip Pirates ownership/management

        Reply
  12. DwayneMurphyFav

    1 month ago

    I honestly feel like ownership deserves more blame for this season. That being said this upcoming season is Ben’s last to right the (pirate) ship

    3
    Reply
    • AI GM

      1 month ago

      Might get another. I mean if CBA doesn’t give Nutting more $ and or they miss games it’s not worth paying 2 presidents gms.

      Reply
  13. AI GM

    1 month ago

    Welcome back Ben! Too much $ obvious choice. A+ non firing.

    Reply
    • Because I was born in PIT

      1 month ago

      The optimist in me wants to believe that Nutting is hoarding some cash to go all in (not Dodgers or Yankees all in of course) in the next year or two while the pitching is so good. Even if he invests a little over what the league gives him it could make a difference. I am also wondering what his annual debt payment is (if any) to the people or institutions that allowed him to purchase the team when they were in or near bankruptcy. Any knowledge on that?

      1
      Reply
      • AI GM

        1 month ago

        I heard he is all in for 2026. All in for Nutting so nothing exciting but more than he has done in a long time. Part with better prospects than normal. Spend more on free agents. Even one that takes more than a 1 year deal. Willing to do another extension.

        No idea about debts bribes standings.

        Attendance was down so that doesn’t help. What he doesn’t realize is he could boost it at any time if he knew or hired anyone who has a clue about marketing and a gm who could utilize funds.

        Reply
        • Because I was born in PIT

          1 month ago

          Thanks.

          1
          Reply
        • greatwhiteangus

          1 month ago

          You heard that, eh? Source? And no, the guy standing at the stall in B-Dubs doesn’t count

          1
          Reply
        • AI GM

          1 month ago

          Greg Brown and person in one of my chat groups.

          Reply
  14. TheRickSays

    1 month ago

    lol what? NH built a playoff team, Cherington can’t get out of the cellar in the division

    1
    Reply
    • greatwhiteangus

      1 month ago

      Bob actually spent some money then. Those 3 magical seasons, over a decade ago, Bob spent over $100MM annually. He hasn’t come close since. And when you add inflation into that Bob is spending barely anything.

      1
      Reply
      • Mendoza Line 215

        1 month ago

        He spent money because Huntington had assembled a team that had the second best record in MlB for the 2013-2015 period.
        An additional player or two could have meant a major difference.
        Cherington can’t even get this team higher than 4 th place in 6 years.
        Easy decision.

        1
        Reply
  15. Appalachian_Outlaw

    1 month ago

    I am not saying Cherington has done a good job, by any stretch- but a change will not fix anything in Pittsburgh while Nutting owns the team. There is no reason not to keep him and hope, against all odds, ownership might spend an extra 5m on payroll. Fire Cherington, and there is no chance of that.

    Reply
  16. casualfan

    1 month ago

    So if I’m Cherington I’m trying to find out who at Milwaukee, Cleveland, and Tampa are assessing the talent and try to hire those guys.

    Reply
    • AI GM

      1 month ago

      Bold strategy. Let’s hope richer teams don’t think to do the same thing but I’ll bet on Nutting outbidding for their services.

      Reply
    • Dock_Elvis

      1 month ago

      Nice thought. But those people also dont want canned when Nutting passes on the torch. They have pretty decent talent evaluators…I exclude Skenes who was an obvious #1 for anyone.

      Reply
  17. Baseball trade conspiracies

    1 month ago

    It’s a sad time for pirate fans. Nutting doesn’t care about winning. Just money. If he was all about winning,cherrington would have been gone last year. The core pitching is here. But they don’t have the management or coaching staff to take advantage of it.
    Kelly is managing in the last 20 games to win to make his resume look good. And it shows how bad he is with the losing streak. When the season is lost after 100 games,you need to manage for next season. Meaning playing players who are young and hungry. Players you know I w who will be here for the future. Not the lineups he’s throwing out there. This is my biggest problem with Kelly. The pirates need a clean sweep of upper management, the manager and coaching. The morale of this team is dismal. What Players want to play in a losing environment. I know I wouldn’t. IF these moves aren’t made,I’m afraid the pirates will never recover.

    1
    Reply
  18. DDRAIG

    1 month ago

    Nutting was a fool to give this length of contract to Cherrington. Together, they are destroying baseball in Pittsburgh. The Pirates will never win under either one.

    1
    Reply
    • Dock_Elvis

      1 month ago

      Destroying? The Pirates have pretty much been in the tank since Jim Leyland was lighting up heaters in the Three Rivers dugout. Outside of that wild card outliers 10 years ago. A person has to be 40 just to recall them being really good.

      Reply
  19. TheMan 3

    1 month ago

    I don’t like Nutting’s greed either and have an equal amount of disrespect for Cherington’s work ethic so I have to ask why Huntington’s tenure took us to the playoffs three years in a row under the same financial constraints?
    Could it be because his team and that of his predecessor knew how to develop draft picks, made trades that benefited this team and made every penny count?
    Cherington has accomplished none of those factors
    Drafting Skenes was a no brainer but the development of position players that he drafted have yet to make a significant impression in the majors

    Reply
    • AI GM

      1 month ago

      Crews was #1 prospect by every major outlet but 1 who had him at 1 until just few weeks before draft. Many pirates fans wanted Crews. “We need bats”

      Huntington was hired when 2007? Didn’t win until 2013. Didn’t have the farm system Cherington has. Might be the best farm system Pirates ever had at least in recent times. Pirates never had this much pitching at least in last 100 or so years. Cherington drafted the best player in draft 3 years in a row.

      Huntington had it easier. Front offices were much dumber dinosaurs back then. Many had little or no analytics department. Even when teams had great success pitching low in zone and shifting they refused to do it.

      You can celebrate the Reds pitcher dropping the ball and Pirates winning 1 wild card game. Ben Cherington has a world series ring as a gm.

      Reply
      • TheMan 3

        1 month ago

        Yeah and a losing record as a GM of the Bucs.
        I get that this farm system is good but I have seen his minor league players do well there and then can’t hit their weight once they play against major league pitching
        Henry Davis and Jack Suwinski come to mind

        Reply
        • AI GM

          1 month ago

          He should have a losing record. He took over a team with no elite talent. What little talent he had needed to be traded. Terrible farm system. Maybe the worst player development in baseball. 2020 21 22 he tried to lose as many games as possible as he should have. 2023 he had the worst injury luck. 2024 they were actually winning record until August. Should have fired Shelton after that. That cost them 2025 as well.

          I was all for firing Cherington until I heard he had 2 years left. That’s too expensive. Williams is even worse so he would have to go as well. Way too expensive. Cherington isn’t so bad that Nutting has to fire him and eat all that $.

          And Nutting is involved. Talks to Cherington daily. Big decisions Cherington informs Williams Nutting and gets their approval. Cherington wanted to make trades and wasn’t allowed to.

          Reply
        • TheMan 3

          1 month ago

          If I recall correctly, Cherington had a rebuilding effort in 2021 which can now be considered an utter failure
          That was 4 years ago and here, 4 years later, he will have to do it again for 2026
          How many chances are we expected to give him?

          Reply
        • AI GM

          1 month ago

          Not a failure at all. Farms loaded and mlb team has young cheap talent. Just need fo supplement it.

          Reply
        • TheMan 3

          1 month ago

          4 years later and they still suck

          Reply
    • greatwhiteangus

      1 month ago

      Huntington still had more money to spend especially when you consider inflation.

      But NH was great at the reclamation project. He didn’t sign any top level available talent. He got guys off of down years, underpaid them and it worked out.

      2
      Reply
  20. grizzled sports vet

    1 month ago

    Here’s the part of the article that is sad, but true (referring to Skenes). He “gives the club their first bonafide ace since Gerrit Cole and should anchor the rotation for the next few years.” Even the writers know that Nutting won’t keep Skenes long term, just like Cole or anybody else at market value.

    Reply
    • AI GM

      1 month ago

      What’s Nutting have to do with it? Small markets can’t keep their aces. With 100 to 130 million payroll you can’t give 30 40 million a year to someone who plays once a week who can get hurt at anytime and miss 1 to 2 seasons.

      Reply
      • greatwhiteangus

        1 month ago

        Exactly. Brewers traded Corbin Burnes. Rays traded Blake Snell, David Price. And eventually we’ll trade Paul Skenes.

        1
        Reply
        • AI GM

          1 month ago

          Rays traded Archer!

          Reply
  21. The Saber-toothed Superfife

    1 month ago

    Gonna have to trade Konnor and Seth……

    That is if you want to speed things up a bit and actually win.

    Reply
    • AI GM

      1 month ago

      They better not. They need KG to win now and SH to replace Skenes Keller. You don’t trade that caliber of prospect. Pirates have enough other quality quantity to get whoever they want.

      Reply
      • greatwhiteangus

        1 month ago

        “to get whoever they want”

        Ummmmm, no??? Unless you mean the next IKF, like Paul Dejong, then you’re spot on.

        Reply
      • The Saber-toothed Superfife

        1 month ago

        The current thing is to bring up prospects early, hoping in a grand entrance. Mostly, it just hinders development.

        Reply
  22. TheMan 3

    1 month ago

    Cherington’s trades haven’t exactly gone very well for the Bucs return
    I wouldn’t trust him to trade one of the Pierogis for another mascot
    Quinn Priester anyone?

    Reply
    • greatwhiteangus

      1 month ago

      I’d think Boston is more upset at that. Plus Priester’s FIP is a run higher than his ERA. Has he improved? Absolutely. Is he winning because Milwaukee is better than Pittsburgh? Totally.

      Reply
      • TheMan 3

        1 month ago

        Milwsukee may be better than the Bucs, Priester’s ERA of 3.25 doesn’t have anything to do with their offense

        Reply
      • AI GM

        1 month ago

        Boston just unloaded their garbage to get Priester. Turned that garbage into 30 something pick in draft and 2 prospects. They’re trying to win a world series so aren’t concerned about Priester at all.

        Reply
  23. Rsox

    1 month ago

    Best case scenario for Cherington is he leaves after ’27 and doesn’t have to be the one to trade Livvy, i mean Skenes…

    Reply
  24. Dock_Elvis

    1 month ago

    As ludicrous as it sounds. Dealing Skenes if franchise altering talent is brought back..just might be the way back for ANY front office trying to pull off the Pittsburgh Miracle. If they had bats to match some arms theyd get it going…then somehow someday find a way to then manage a winning organization.

    Reply
    • TheMan 3

      1 month ago

      It was reported a few weeks ago that the Yankees offered their two top prospects for Skenes and Ben obviously refused, because he wanted more than two players

      Reply
      • TJECK109

        1 month ago

        Ben would never find another job anywhere if he settled for their top 2 prospects

        1
        Reply
      • Baseball trade conspiracies

        1 month ago

        Yea he probably wanted the bat boy and a bathroom attendant

        Reply
    • joew

      1 month ago

      Skenes is franchise altering. Its barely arguable he is the Best pitcher in the NL and a real argument for the MLB. Skenes only draw back is he doesn’t get the inning count of a ‘work horse’ but still pretty darn good. A touch more efficiency and better management could change that. Still its great for being 23

      In order to even think about it with in the next year or two, you would have to offer a top10ish near term over all prospect (depending on how BC rates them) and still quite a bit more. OR basically your whole farm system (/s) if you don’t have something along those lines.

      some teams can offer quantity of above average prospects though, I suppose you could say franchise altering if you have a dozen top 100 prospects coming up the next year or three even if they’re not ‘elite’ quality

      Reply
      • Baseball trade conspiracies

        1 month ago

        The reason why he isn’t getting the “inning count”, is because of mismanagement by moron 1and moron 2. That being Kelly/Shelton and cherrington. Don’t buy the crsp about the pitch count or innings. The kid is 6’5 240lbs. Hes a throwback. Im betting he could get between 250 and 300 innings a year. But as long as he pitches for the pirates,FORGET IT. I hope not,but probably, he will be dealt. Then people will see the real PHENOM.

        Reply
        • joew

          1 month ago

          @trade

          First part I agree, the management of paul’s pitches/innings could’ve been a lot better

          and yeah I buy pitch count totally, but I also know that pitch count should fluctuate from player to player and game to game. given his delivery and as effortlessly he throws 120pitches seems like it would be do able with little concern.

          BUT the pirates don’t want to risk losing paul at 23 in a throw away season. If they had any shot they probably would’ve been more aggressive with him, until that time don’t risk your most valuable trade piece lol

          Reply
  25. MLBTR needs to hire editors

    3 weeks ago

    “Impressive as the pitching group has been” is NOT proper English. You can’t just leave out “as” at the beginning because you feel like it. You’re a professional writer so grammar isn’t optional.

    Reply

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    Trevor Story To Decline Opt-Out Clause, Will Remain With Red Sox

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    Recent

    White Sox Notes: Free Agency, Hitting Coaches, Young Bats

    Emmanuel Clase, Luis Ortiz Indicted On Gambling Charges

    Minasian: Giants Will Prioritize Adding Pitching Depth

    Christian Roa Elects Free Agency

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    Brewers Release Tucker Davidson

    Padres Coaching Notes: Niebla, Fritz, Bench Coach

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