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    Home Sports Pirates' trade deadline defined by rigid thinking and poor processes. What else is new?
    Pirates’ trade deadline defined by rigid thinking and poor processes. What else is new?
    National Sports
    August 1, 2025

    Pirates’ trade deadline defined by rigid thinking and poor processes. What else is new?

    By JASON MACKEY Pittsburgh Post-Gazette

    (TNS) — Four years ago, the Pirates eschewed a traditional draft strategy and instead took Henry Davis No. 1 overall, using the savings to sign other players. Bubba Chandler might have to be Paul Skenes-level good to call what the Pirates did a success.

    In 2022, they took Bryan Reynolds — their best player at the time — to arbitration over $650,000, a laughably small sum considering his status.

    It’s the same type of thinking we saw Thursday with the mess the Pirates made around the trade deadline.

    The moves were right because they made them, the thinking correct because it was theirs. How could anyone on the outside possibly see it differently?

    “I feel really good about the things we did,” general manager Ben Cherington insisted. “We put ourselves in a stronger position going into August, September and the offseason.

    “Of course, there was more we wish we could have done. We’ll just have to get back to that in November.”

    Once more — and with gusto — let’s all hope that doesn’t happen.

    Owner Bob Nutting should’ve fired Cherington last offseason. I really hope he grasps how frustrated and disenchanted people have become with the Pirates and either sells the team or steers it in a better direction come October — one that eliminates these head-in-the-sand moments that have unfortunately defined the Pirates since 2019, things that the organization and its fans see differently.

    We could talk about Rodolfo Castro’s cell phone, Ke’Bryan Hayes munching on sunflower seeds or missing first base on a home run, even Will Craig chasing someone back to home. That’s one version.

    There’s also sending Cole Tucker to Bradenton for “skill development,” laughing at reporters for asking what someone was working on, or any number of on-field decisions — pulling starters, lineup construction or strategy.

    Always an answer. A convicted one, too. More often than not, it just hasn’t been correct.

    That way of operating contributed to one of the darkest days for the Pirates that I’ve seen, where the overarching goal was difficult to explain and even tougher to believe.

    They shed salary to spend this offseason and vowed to essentially return to team-building and improvement during a second phase this winter, perhaps forgetting that people:

    —Don’t trust Nutting to spend money

    —Don’t trust Cherington to spend what funds he does receive appropriately

    Why should anyone believe them? Because they said so? It makes no sense.

    Especially when you try to think through what they did on Thursday and their explanations for the moves.

    ‘Didn’t feel like we had to trade anybody’

    That quote came from Cherington’s post-deadline availability. The context involved us asking why the Pirates didn’t trade Andrew Heaney, Isiah Kiner-Falefa and Tommy Pham, who are on expiring contracts.

    Like every team, the Pirates establish value for players. They also appraise what others are offering. But it’s not black-and-white, especially when you’re talking about guys on expiring deals.

    Heaney, Kiner-Falefa and Pham will leave after the season. In the meantime, they’ll also likely take reps away from young guys who could at least have a chance to become part of the future.

    Knowing that, the value line should change.

    If you’re not getting what you wanted at 3 p.m. it’s probably time to adjust. Certainly around 5 or 5:30 p.m. when the deadline draws near.

    But, no. Not here. Not with this ever-convicted group.

    They stuck to their guns and refused to budge, the same as with Reynolds.

    Now, you have two guys (Heaney and Pham) who played in the 2023 World Series, plus another who spent a lot of time with the Yankees (Kiner-Falefa) about to experience September at an empty PNC Park, on a team where they’re nowhere near the focus but also need to play well to sustain their careers.

    Yeah, no potential problems there.

    ‘More than free agency’

    During another part of his Zoom call, Cherington had the ball sitting there on a tee. He didn’t even swing.

    Given the salary the Pirates shed, someone asked Cherington whether that meant they’d be more active in free agency.

    The easy answer: yes.

    Cherington went another route.

    “Could be,” Cherington said. “I think we need to get into it — trades and internal improvement, too. Internal players and internal improvement are the areas we’re always gonna rely on more than free agency. We’ve got to operate well and excel in those areas. But, sure, we’ll be open-minded about free agency.”

    Fans care. They want to see and hear their financial and emotional investment reciprocated by those in charge. With their words and actions, the Pirates did a horrible job of that on Thursday.

    ‘It was our estimation’

    Let’s focus on the David Bednar trade for a second. Rafael Flores, the Yankees’ 2024 Minor League Player of the Year, as the headliner actually makes some sense.

    However, that’s also where it breaks down for me.

    “Feel really strongly about the return,” Cherington said. “We had access to players who were ranked [on top-100 prospect lists]. We preferred this package.”

    So, let me get this straight: The Pirates had access to at least one top-100 prospect … but declined?

    There also could be a logical explanation here involving the Phillies and an 18-year-old catcher named Eduardo Tait, who’s a top-100 guy (No. 56). Flores is closer to the majors, so I sort of understanding preferring that route.

    However:

    —You don’t need to say you had access to better players.

    —Just because they like one specific hitter (or three), why should anyone believe they’ll properly execute a pitching-for-hitting swap?

    There’s also no requirement to trade Bednar now. If the return isn’t there, why not revisit in the offseason? Instead, it feels like a panic move that will only change if Flores turns out to be really good.

    Hardly a sure thing with this group.

    ‘Probably a good idea’

    There’s much to dislike about the Bailey Falter trade.

    They got rid of a solid left-handed starter with a 3.73 ERA who made $2.2 million, effectively because he was due a raise next season and one the Pirates thought would exceed his production.

    I disagree.

    Right now, Falter’s 1.2 Wins Above Replacement (per Baseball Reference) would be worth upwards of $9 million on the free agent market. The return is also lousy, the Pirates getting a 28-year-old reliever with 5 1/3 innings of MLB experience and a High-A outfielder who wasn’t drafted last year.

    But the biggest problem might be the short-sighted thinking with Heaney.

    “We felt it was probably a good idea to trade one starter,” Cherington said. “We were open to trading more if the return was right and just didn’t find those opportunities.

    “Once we knew that the Falter trade was happening, we just decided to hold on Andrew.”

    This would indicate the Pirates jumped at Falter due to the aforementioned return, then decided to keep Heaney either because they hurt their leverage, refused to adjust or potentially both.

    It was yet another case of unnecessary rigidity along with more failure and frustration, outcomes that have unfortunately defined this Pirates regime.

    The Bradford Era

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