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Pirates Showing Interest In Jack Flaherty

By Steve Adams | December 4, 2023 at 12:45pm CDT

The Pirates are among the teams with some interest in free agent righty Jack Flaherty, reports Jeff Jones of the Belleville News-Democrat. The Bucs are interested in a short-term pact with their former division-rival, per Jones.

Interest on a short-term deal, of course, is contingent on how the remainder of the market views Flaherty. At 28 years of age, he’s the youngest starting pitcher with ample big league experience available this winter. However, Flaherty is also coming off a down season that saw him pitch to a 4.99 ERA in 144 1/3 innings between the Cardinals and the Orioles, who acquired him prior to the trade deadline.

Not long ago, Flaherty looked like a burgeoning ace. The former first-round pick and top prospect turned in a 3.34 ERA over 151 innings back in 2018, his first full big league season, and followed it up with even better numbers. At a time when most pitchers in the league were falling victim to what we now know was a juiced ball in 2019, Flaherty was delivering the best season of his still-young career: 196 1/3 innings, 2.75 ERA, 29.9% strikeout rate, 7.1% walk rate. Unfortunately for both him and the Cardinals, injuries (primarily shoulder troubles) limited him to 154 1/3 innings from 2020-22 combined. Last year marked a return to better health but also lesser results.

Flaherty figures to have multiple scenarios he could pursue. A straight one-year deal or perhaps a two- or three-year pact with an opt-out would allow him the opportunity to reenter free agency not far down the road — ideally on the heels of a better platform season. In the past, a straight one-year deal was often the norm for a player in this situation. Increasingly, however, we’ve seen free agents coax two-year deals out of teams, with the second season being a player option.

There’s also the possibility of pursuing a more conventional, longer-term deal that’d still allow Flaherty to return to market at a reasonably young age. In the past, we’ve seen some free agents around the same age (e.g. Phil Hughes, Tyler Chatwood) take three-year deals that provided some financial security while also affording an opportunity to get back to the market in time for another chance at a contract of note. A three-year deal for Flaherty would cover his age-28, age-29 and age-30 seasons. If the market bears it, that arrangement could effectively set Flaherty for life financially and still create the chance to hit the market in search of a more elusive five- or six-year commitment.

As for the specific fit with the Pirates — it’s a strong one, regardless of which type of contractual structure Flaherty prefers. While Pirates ownership might balk at a multi-year commitment of note, Pittsburgh is in dire need of rotation help. Mitch Keller is the only established starter on the roster now that righty Johan Oviedo will miss the 2024 season due to Tommy John surgery. Flaherty would slot comfortably into the starting staff and do so knowing that he’d have a long leash regardless of how he starts the season. Other options on the Pittsburgh staff currently include Bailey Falter, Roansy Contreras, Quinn Priester and Luis Ortiz. This past season’s No. 1 overall pick, right-hander Paul Skenes, will likely debut at some point in 2024 as well.

With regard to the team’s payroll, the Pirates only have three players under contract for the 2024 season (Ke’Bryan Hayes, Bryan Reynolds, Ryan Borucki) and another four arbitration-eligible players (Keller, David Bednar, Connor Joe, JT Brubaker). Roster Resource projects just a $53MM payroll for the upcoming season. Even by the Buccos’ standards, that’s at the bottom of the scale. Pittsburgh opened the 2023 season at $73MM and operated under a franchise-record $100MM back in 2016. There ought to be plenty of room to add multiple starters — even if some money is perhaps earmarked for another reunion with Pirates icon Andrew McCutchen.

Whether Flaherty is a part of the solution or not, the Pirates simply need to bring in multiple arms this winter. Flaherty’s youth and track record (particularly that 2018-19 run) give him more upside than most free agents in the second and third tiers of free agency, but that might also make him a popular target and push the bidding beyond the comfort zone of the perennially low-spending Pirates.

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Pittsburgh Pirates Jack Flaherty

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62 Comments

  1. RonDarlingShouldntBeInTheHallOfFame

    2 years ago

    Perfect stop for him to try and rebuild his value.

    4
    Reply
    • stymeedone

      2 years ago

      Sure,the Pirates are interested in him. The real question: Is he interested in the Pirates?

      1
      Reply
  2. just_thinkin

    2 years ago

    Oriole fan here. Something ain’t right with this dude. So much nibbling for a guy with pretty good stuff. After the trade his first start was fantastic, and then everything after was a wet fart. Just total lack of command, looked like he was afraid of the zone. Guys on base constantly. I dunno. Didn’t really mesh with the vibe of the team either. Was pretty clear Elias was trying to get Cease or somebody else, and had to settle at the last minute.

    I like the guy though and hope he does well. Going back to the NL probably makes sense.

    11
    Reply
    • baseballpun

      2 years ago

      It seems like every starter the Cardinals have developed over the last 7-8 years tries to nibble at the edges. Every batter gets 9 pitches and they’re all out in the 4th inning.

      6
      Reply
      • Dotnet22

        2 years ago

        @baseballpun Nailed it. Not sure if that’s the plan set down by the pitching coach or what but it’s like they’re all scared to throw strikes.

        1
        Reply
    • O'sSayCanYouSee

      2 years ago

      @ just_thinkin — Good assessment of Jake in Bird Land. He never attacked hitters…wasted pitch after pitch, then was upset when it was a walk or a hitter sat on his heater on a full count and tagged it. He should have learned from Bradish, who used to have the same difficulty of being in the zone rather than around it.

      I wish him luck, he does have the tools ..maybe not the strategy yet.

      Reply
    • THEY LIVE!!!

      2 years ago

      Something isn’t right with Jack. He needs to be reprogrammed before he goes full Kapernick.

      5
      Reply
    • Rantucky

      2 years ago

      He hasn’t been right since having shoulder soreness.

      Reply
  3. The Natural

    2 years ago

    Flaherty looked like he’d be an ace for a decade when he first came up…but. He got hurt, fell off the cliff and has never been consistent at all afterwards.

    2
    Reply
    • baseballpun

      2 years ago

      They chose him over Alcantera and it looked like the right decision for about a year. Then it went very, very bad.

      Reply
  4. theathlete

    2 years ago

    Flaherty has horrible body language on the mound. He just looks miserable the entire time, like he’s struggling, and frustrated. I think it gives opposing hitters confidence against him.

    3
    Reply
    • just_thinkin

      2 years ago

      The body language was for sure a surprise when we traded for him. Might just be how he looks and that’s fine, but it was a stark difference from our other starters, even our young guys.

      The impression I had was a guy who knows he doesn’t know how to find whatever it was that made him good, and just going out there and trying to will it to happen. It’s just not there. He might need to retool his whole repertoire or mechanics or something. Maybe a switch to reliever at some point.

      2
      Reply
    • O'sSayCanYouSee

      2 years ago

      @ theathlete — Yes! Body language is of a borderline psychopathic. And hitters looked cool and relaxed against him, waiting for the self-destructive next pitch he threw. So hard to watch. Hope he finds his chi.

      1
      Reply
      • CityofChampions

        2 years ago

        There’s a picture of the O’s clinching either a playoff birth or the division and everyone is celebrating together besides Flaherty. He’s out all by himself.

        I don’t know what it is with him but there’s something that seems a little off. I know he won’t be back in Baltimore. He’s been declining for awhile now. The numbers under the surface don’t look great. Elias obviously thought there was upside & maybe there is. But I would take the bet that he never returns to those #2 starter days.

        1
        Reply
    • Rsox

      2 years ago

      Flaherty seems to treat playing Baseball like a menial job you do, not because you want to, but because you have to to make ends meet.

      Bret Boone tells a story about how in spring training in 2006 he was in Mets camp on a minor league contract. When he was informed that he had won the Second Base job he announced his retirement. When asked “why?” He said it was because when he woke up that morning to go to the ballpark it felt like going to work and at that point he knew it was time to walk away

      1
      Reply
      • CityofChampions

        2 years ago

        It’s honestly fine if he treats baseball like a job and doesn’t really enjoy it. So long as he puts in the hours of work and listens to the coaches adjustments.

        You want 26 baseball loving guys but that probably won’t be the reality. I don’t know anything about his personal situation but he certainly didn’t seem to enjoy the O’s.

        Reply
        • CityofChampions

          2 years ago

          With that being said—wouldn’t want to give him a bunch of guaranteed years. A contract structured like Lugo’s or Wacha’s makes sense to me. I don’t want to guarantee him multiple years and hope he stays committed.

          Reply
  5. THEY LIVE!!!

    2 years ago

    Flaherty squandered his talents. His flair for being a social justice warrior suggests he is conflicted & needs psychiatric help. Maybe a stint in Japan will straighten him out.

    18
    Reply
    • jdgoat

      2 years ago

      You political zealots are so weird to me.

      7
      Reply
      • THEY LIVE!!!

        2 years ago

        @jdgoat
        You don’t even know my politics because I’m non-political. Flaherty though is an out spoken critic of the police as well as law & order. But you probably don’t think he’s weird at all.

        1
        Reply
        • jdgoat

          2 years ago

          I think it’s odd that you think he needs psychiatric help for being against police brutality. You’d think that would be the sane stance in a society.

          7
          Reply
        • THEY LIVE!!!

          2 years ago

          Everyone is against police brutality including me.
          Not everyone though thinks everyone in law enforcement engages in it. Flaherty doesn’t know when to keep his mouth shut about things he knows nothing about.

          1
          Reply
        • jimmyz

          2 years ago

          @THEY LIVE nobody here needs to know and likely doesn’t care about your personal politics. But we all can factually see that every comment you posted on this thread is politically based and has nothing to do with baseball

          2
          Reply
        • THEY LIVE!!!

          2 years ago

          @Jinnyz
          Let me clarify. Jack Flaherty sucks as a pitcher and is even worse in the clubhouse. Lastly, I wouldn’t want my kids to emulate this putz. Jack is on par with Trevor Bauer except Bauer can get batters out.

          Reply
    • AHH-Rox

      2 years ago

      Damn, they really need to fix the mute button on this app.

      1
      Reply
  6. Old York

    2 years ago

    Honestly, I like this move and think there is still potential with Jack. If you look at his kwERA and GBkwERA over the years, it’s not horrible. He’s not a #1 by any means but I could see him in a #4 or #5 role with no pressure with the Pirates helping him get back into form. But you can’t think of him as the ace of the staff.

    kwERA
    2017: 4.12
    2018: 3.00
    2019: 2.66
    2020: 3.07
    2021: 3.20
    2022: 4.61
    2023: 3.89
    Career: 3.28

    GBkwERA
    2017: 3.91
    2018: 2.98
    2019: 2.68
    2020: 3.04
    2021: 3.23
    2022: 4.59
    2023: 3.84
    Career: 3.26

    Reply
  7. PiratesPundit51

    2 years ago

    I’m fine with the Pirates kicking the tires here, given the need for multiple starters even before Oviedo’s injury. If he can be had without hurting their ability to add at least another starting pitcher or address some of the other holes on the team, then go for it. I think Flaherty will get an overpay from one of the usual suspects who can afford a miss with him; the Pirates’ offer surely won’t be the best one in terms of short-term overall money, but may give him an opportunity to re-enter the market sooner with a more recent resume of serviceable starting pitching.

    If Flaherty bombs in a big market on a 2 or 3-yr pact, his next contract might be a minor league one, but he’ll have $15-20 million in his pocket; or he can sign with Pirates for a little less, re-enter the market in a year or two and possibly command considerably more – it’s like watching a game show where you take the sure money, or risk it for a chance to make a lot more.

    1
    Reply
  8. steelerbravenation

    2 years ago

    Sign Flaherty & trade for Marco Gonzalez
    Sign Rowdy
    Trade for Drury
    Bring back Cutch
    Call it an off-season

    Reply
    • PiratesPundit51

      2 years ago

      Marco is already gone, and for WAY more than the Pirates would have given up to get him. They already have Rowdy in the system – his name is Mason Martin. Triolo is younger and cheaper than Drury; as one of the Angels’ few in-demand assets, he’d cost more in the long run than the Pirates ought to pay (for someone who’s signed at $8.5 million for only one more season).

      I wouldn’t disagree with you in terms Drury slotting in as the team’s primary 2B, I feel like his salary would limit what the Pirates MUST do in terms of their pitching situation. It’s dire enough that even Cutch might start looking like a luxury they can’t afford.

      1
      Reply
      • YourDreamGM

        2 years ago

        Marco trade hasn’t shown up on mlbtr yet, only looking to trade him. Until then it hasn’t happened as far as I am concerned. Don’t got time to be looking through all the X people.

        Reply
  9. Deez Cardinals

    2 years ago

    Another I say good luck with your future endeavors! Entitled attitude. He remained an ace in his own mind long after the results failed him. He at one time said no home town discounts as this is a business. Well business now takes him to Pittsburgh possibly on a contract he would have never dreamed 4 years ago.

    3
    Reply
  10. Lefty_Orioles_Fan

    2 years ago

    I thought the Oriolea should sign him to a one year deal
    Cripes they gave up two players for him
    If the Pirates sign him so be it, but if someone could fix him, more power to that team

    Jack still has nasty stuff, i don’t know what the real issue is

    1
    Reply
    • just_thinkin

      2 years ago

      Did you not watch his starts? I mean… he didn’t know where the ball was going. Why would you want to sign him instead of someone like Wacha? Hopefully we aim higher than Wacha, but I’m just saying. There are better guys available, and only 1-2 rotation spots available on the O’s.

      3
      Reply
    • Deez Cardinals

      2 years ago

      He seemed excited to be there. I’m surprised as well. Might have been a good fit to stay in Baltimore

      Reply
  11. TJW

    2 years ago

    Sure sign your career has taken a downward turn.

    1
    Reply
  12. YourDreamGM

    2 years ago

    I think he would be depending on contract a fine 4 5. After reading comments he is sjw woke I wouldn’t want him. Don’t care what superstars or a list actors opinions are on things. Definitely don’t care what this nobody thinks. I’m in the minority here. Most people are fine with these egotistical people telling them what to do. People are still watching sports and movies. I am down to just baseball and should have stopped watching it and I have drastically cut down on my viewing. As a multi racial 3rd gender I don’t need you to tell me that my life matters or wear a patch on your jersey. Just shut the f up and throw your lil baseball ok.

    Again it’s just me. I am sure all the white straight people think they are doing such wonderful things. Seeing signs, flags, and patches has surely changed so many lives. Jack and anyone else has the right to say whatever they want. I just have the right to find it annoying.

    5
    Reply
    • Mendoza Line 215

      2 years ago

      Dream- FWIW I find that to be a fine attitude.

      1
      Reply
      • YourDreamGM

        2 years ago

        We can be friends Mendoza. I think we already are.

        I will give a F grade to whoever signs this guy. He isn’t good enough to justify the risk of disrupting the team. Guy just sounds like someone I would call a bag.

        Reply
        • Mendoza Line 215

          2 years ago

          I like most of the Bucco regular posters here including you Dream as one of the most liked.
          We all add a different take and knowledge.to the subjects.
          I rarely venture into other team’s threads but there seems to be more contention in many of the ones that I read.
          I give thanks that the Bucs were decent this year and the trolls seemed to move on to other teams.
          I often wonder what it would be like to get this gang into one big room and kibbutz.
          Impossible to do but I think that we would mostly be talking about one of our favorite subjects.

          1
          Reply
        • Mendoza Line 215

          2 years ago

          Dream- I think that the Pirates need starting pitching very badly and they may be able to get him cheaply.
          Young men grow and mature at different rates.
          If he is still the type as one poster stated about the Rays to criticize others about their beliefs then that is a red flag,and I think that your assessment may still apply.
          With Jim Leyland making the HOF yesterday I saw his rant against Bonds and he asked his coach whether he should get rid of him and the coach said yes.When the coach asked him whether he would,he said no.
          He knew that he needed him to compete.
          If they are serious about signing him they owe it to themselves to have a sit down with Flaherty and his agent and ask him pointed questions.I think that he was once a fine pitcher and as such he can possibly return to being one.

          1
          Reply
  13. Player to be named in the future 2

    2 years ago

    Matt Harvey 2.0

    1
    Reply
  14. TJW

    2 years ago

    Yeah, nobody in St. Louis misses him.

    3
    Reply
    • User 1404051815

      2 years ago

      I’m at a loss as to how a “retired military officer” like yourself supports the stain of humanity, a guy who with every speech makes it clear he’d use the office of president for retribution of political enemies if re-elected while at the same time denigrating some athlete for employing the idea of free speech
      Just what military did you serve?
      Retired? Good riddance, indeed

      2
      Reply
      • User 1404051815

        2 years ago

        Rez, take a look at the arrow. Certainly wasn’t directed at you

        Reply
      • misterfigs

        2 years ago

        @Rezimodos, that’s hilarious. Maybe a US Government or Civics course is needed for you. You’re going to compare what we’re hearing now to past presidencies?
        Turn off the NewsMax for a minute and listen before you embarrass yourself with such pronouncements.

        1
        Reply
      • YourDreamGM

        2 years ago

        I never seen arrows on the website. If everyone seen arrows there would be no one using @.

        1
        Reply
      • YourDreamGM

        2 years ago

        I think it’s cute people root for these old white guys like they do a baseball team.

        Personally I find both of them to be 2 of the worst humans I ever seen. I find one to be a better president but not good enough to defend against strangers on a baseball discussion comment section.

        1
        Reply
      • Mendoza Line 215

        2 years ago

        I see indents on my IPad but they are difficult to see.I usually address the poster by an abbreviation of their address.

        2
        Reply
  15. CaseyAbell

    2 years ago

    Didn’t know about Flaherty’s politics and don’t care about ’em. But his career has fallen apart completely since 2019. He’s become replacement level at best as the walk rate has pushed higher.

    That said, replacement level pitchers are getting paid and Flaherty will be 28 next year. Pittsburgh just needs people to fill the rotation, so the team might be desperate enough to give Flaherty real money. He won’t get them to the postseason but the Pirates probably aren’t going to contend, anyway.

    1
    Reply
  16. THEY LIVE!!!

    2 years ago

    Flaherty’s performance fell off coincidentally with his public display of unity with BLM and Antifa in 2020. The Cardinals didn’t want him back either, hence no extension and they need pitching badly.

    2
    Reply
  17. Grumpofm

    2 years ago

    1 year for 6 mil with incentives to make up to 9. Team option for a second year for 10. Gives him a shot and helps the BUCS.

    Reply
    • Mendoza Line 215

      2 years ago

      Grump- Good post.I think that he would be a good addition under that scenario.I do not care about his politics but if he is arrogant enough to think that because he is a professional baseball player his opinions are better than others’ then his lack of character in this regard can portend problems otherwise including those adversely affecting his career livelihood.

      Reply
      • Grumpofm

        2 years ago

        Thanks. I don’t care much about his politics, or any player’s to be honest with you. Since most post game interviews go to the players of the game, I also don’t believe he’d have as much of a platform in Pittsburgh. He won’t have as many opportunities as a pitcher.

        Reply
        • YourDreamGM

          2 years ago

          I think to have the best possible team you need strong chemistry. Unless everyone on the team agrees with his views it’s going to lower the chemistry potential. I dunno about you guys (and I use guys as a general term like people so if any of our 7 female community members see this please don’t excluded) but my closest friends are the ones who are like minded. And I am a critical thinker. I can imagine what it’s like for 97 percent of most people.

          Reply
  18. Mendoza Line 215

    2 years ago

    I’m an amateur presidential scholar and in my opinion,FWIW.this great Country has lacked leadership over the last twenty years in a similiar vein as in only one other period.That occurred before and after the Civil War,and that includes Lincoln after his election and before his inauguration.
    Candidates have to put up with so much crap to run now that those like Colin Powell who would have made a fine president chose not to run.
    I am a proud independent and hope for the Country’s sake that a third party enters the fray.
    It,like baseball,is much too great to lose.

    Reply
    • YourDreamGM

      2 years ago

      I think people are the problem. There have been much better people run for president and people didn’t like them. I find 97 percent of people to be stupid. Like there is 2 main political parties and 90 some percent of people identify with 1 of them! I got no use for a R or a D. I think it’s over. I hope I live long enough to see Mad Max.

      Reply
      • Mendoza Line 215

        2 years ago

        I have faith in America and the American people.
        Unfortunately,I do not necessarily disagree with what you said.
        I would not say stupid but stuck in their ways and not open minded.
        But if there is good and smart and honest political leadership the two party system can work,and reasonably well.

        1
        Reply
        • YourDreamGM

          2 years ago

          I find majority of people stupid. Also think they are stuck in their minds and not open-minded. Fine to disagree. I am in the vast minority. I see things others do not. I have those They Live sunglasses. I am unrelatable to most people.

          Reply
  19. Big cheese G stands for grilled

    2 years ago

    Plenty of quality innings left untapped in Flaherty. Astros would be a good fit.

    Reply
  20. Wheeler Dealer

    2 years ago

    Is Ray Searage still the pitching coach? He could fix this guy

    Reply
    • Mendoza Line 215

      2 years ago

      He left after the 2019 season with Huntington and Hurdle.
      Ray was good fixing mechanical issues not mental or emotional ones.
      He mainly reinvigorated veteran pitchers.

      1
      Reply
  21. joew

    2 years ago

    On one hand i want a 3year+ deal. On the other hand i’m not so sure a 1 year deal is good.

    BUT even with his poor performance he still got in 140 innings last year. Not a huge amount but even if it is shaky play eating up some innings while Skenes gets ready isn’t nothing.

    The still need a more ‘sure thing’ pitcher.

    Reply

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