The Wolf of Federal Street

The Pittsburgh Pirates Continue to Disappoint at the Trade Deadline

Aug 01, 2025

There’s a reason I’ve been quiet this year: Perspective.

For the last decade and a half, I’ve been an expert on baseball and specifically the Pittsburgh Pirates.

The human mind is only designed to contain so much active information. As a full-time writer, my mind spent years in a job where I could actively recall information about a revolving door of nearly 200 minor league players and their history with the Pirates, along with the Major League roster in Pittsburgh, the payroll, the depth chart of the team, and the relevant history of the franchise.

That doesn’t leave a lot of room for real life. I have respect for any reporter who is going through the grind right now. They are committing their minds to an area of reality that most people turn to for an entertaining escape from real life — with the escape of most fans depending upon the intense knowledge of those reporters.

My perspective this year has been an attempt to view the game as a normal fan.

Every day, I wake up and go to “work” trading on the stock market.

On Wednesday morning, I woke up, spent a few hours closing out short-term positions, opened one long-term position, and spent a few more hours researching and opening one additional trade. Around 2 PM, I sat down and watched the financial news with Chairman of the Federal Reserve Jerome Powell explaining the reasoning for the Fed maintaining rates in their latest meeting.

Around the time I finished work for the day, I logged into X and saw that the Pirates had traded Ke’Bryan Hayes.

When I was a full-time sports writer, I would be on call nearly 24/7 during this time of year, waiting to report the news of the latest trade. People who were turning their attention away from their work lives would check out Pirates Prospects to get my instant analysis on the latest moves, along with the first bits of information gathered on the new players entering the system.

This will not be one of those updates.

I wrote this column on Wednesday night, but like dozens of columns I’ve written this year, I walked away from my computer without publishing. In this case, I decided I was going to wait until the trade deadline had passed to give a complete reaction.

Having said that, the David Bednar trade on Thursday did nothing to change the tone of this column, and only added to the pre-existing critique of what has been happening with the Pirates.

I’m mentioning this because most of this column will be centered around the Hayes trade, with mentions of other trades added in during my Thursday edits.

The Ke’Bryan Hayes Trade

While observing some of the analysis from Pirates reporters on the Hayes deal, and even the Bednar deal, I was reminded of why I used to be called an apologist by some fans.

As a reporter, you need to be objective. You can’t give your opinion on what the team should do, and instead, you base your view on what the team is actually doing. You can’t view yourself as a scout with a competing opinion, and instead need to rely on the scouting reports the industry provides.

It’s a difficult tightrope to walk, though there is value in this approach.

We all need people who get inside the minds of the decision makers and explain the thought process of any move from their perspective. When I was reporting, I would have rather been called an apologist for trying to accurately explain what the Pirates were intending to do, rather than taking a stance on what I thought they should have done. Granted, I also gave my opinions on their moves — both positive and negative — as I can compartmentalize my thought process across different viewpoints at the same time.

From the Hayes trade, what I’ve gathered from Pittsburgh reporters, and social media accounts meant to influence the public thinking, is the following:

The Pirates felt the contract of Hayes was too much for his lack of hitting. Hayes is owed $7-8 M per year through the 2029 season, with a $12 M club option in 2030.
Jared Triolo offers a great defensive alternative, even if his offense is the same or worse.
There was speculation that the Pirates could target an offensive upgrade at third base this offseason with the savings from Hayes.
The Pirates received A-ball infielder Sammy Stafura and MLB reliever Taylor Rogers. The former was the number nine prospect for the Reds, via MLB Pipeline. The Pirates flipped Rogers to the Cubs for outfield prospect Ivan Brethowr.

As someone who isn’t trying to be a prospect expert and educate you on every detail of this trade, I’m going to give you my opinions.

These opinions come from the perspective of someone who is trying to see the game as an entertainment source, from the limited information level of the average fan.

My disclaimer is that I’m not a fan of the Pirates. I have pulled for this team for two decades to create a great story by winning against the odds in MLB, but it’s very easy for me to ignore this team when it’s not my job to cover them.

At this point, I just feel bad for the fans of the team.

Scouting Ke’Bryan Hayes

I’m a fan of Ke’Bryan Hayes.

Hayes was drafted by the Pirates out of high school, and I interviewed him many times following his selection, and into his career in the Majors. I’ve always had a great deal of respect for his drive and work ethic, especially when battling adversity.

As a prep player, Hayes took it upon himself to create a mountain biking routine, which allowed him to get in better shape, leading to him becoming a first round draft prospect in 2015. My scouting view always looks for people who successfully implement a change to improve the pursuit of their goals. The players who can successfully change themselves with a goal of improvement are the players who make the Majors. It was never a question for me that Hayes would reach the Majors and excel when he did.

The value of Hayes is a touchy subject in Pittsburgh.

A Gold Glove winner in 2023, Hayes is one of the best defenders in the game. His defensive value this year ranks fifth overall among all positions, and he’s by far the best defensive third baseman. Hayes could receive his second Gold Glove this season, as no other third baseman is close to his defensive value.

Offensively, Hayes is one of the worst hitters in the game this year. While he ranks fifth defensively among 156 qualified players across all positions, he ranks last in that same group for his offensive value. His defensive value at third base is more than double the value of the second best defender, Ryan McMahon, but the better offense from McMahon gives him twice the overall value of Hayes.

One of the legitimate concerns from Hayes is a history of back issues, which cost him time and drained his numbers across the board in 2024. His power has dropped significantly since a breakout in 2023, and that power output is currently half of what it was when Pirates fans were hoping for more power in 2021-22.

So, I get the concern surrounding him.

Back issues are no joke, and only get worse as you get older. There are ways you can reverse the negative trend and deal with the pain, but that takes time and is not a guarantee. There is no guarantee that Hayes improves his offense from here, which means he’s likely a defensive specialist, an overall below-average starter, and if the defense ever slips like it did in 2024, he’s got negative value.

I would bet on Hayes, because he’s the type of person who will look for ways to improve, even with radical approaches to get his body in better shape.

Technically, Hayes did improve this year over last year, even if the improvement wasn’t shown in the stat sheet. The back issues hampered his defense in 2024, but he’s returned to being a Gold Glove third baseman. The overall offense is still among the worst in the game, but there are positive signs. His exit velocity, barrel rate, and hard hit rates are all up from last year, even if they’re all down from 2023.

If Hayes continues this recovery and improvement with the Reds — a team that has less of an emergent need for offense and more of a need for the defense Hayes provides (according to Reds reporters I saw reacting to the deal) — then this trade could haunt the Pirates for the rest of the decade. Not only is Hayes a Gold Glove third baseman, but he would be a tremendous value at $7-8 M per year if he starts hitting.

I’m going to point out that the Pirates, last year, added Isiah Kiner-Falefa at the trade deadline, giving him a starting role with a similar salary.

Kiner-Falefa plays a more valuable position, but is largely the same profile as Hayes. His offensive value is better, but his defensive value isn’t as good, ranking 31st among MLB shortstops this year. Hayes is more valuable than Kiner-Falefa, yet the Pirates took on the salary of one, while trying to rid themselves of the other contract.

The Pirates retained Kiner-Falefa through the deadline, despite his pending free agency and $7.5 million salary this season.

The Trade Return

Alright, so maybe I’m not the average fan.

Most fans aren’t default checking Baseball Savant for barrel rates when breaking down a deal. Some habits are hard to break.

What I’m not going to do is give you a detailed prospect report on Sammy Stafura. He was a second rounder in 2023, and is a 20-year-old shortstop in Low-A. That means he will likely be playing for the Bradenton Marauders this year, and if all goes well, he could arrive in the Majors by 2028-29.

My future outlook right now extends no further than options contracts on September 19th and October 17th. By the time Stafura arrives, if he arrives, I don’t even think Paul Skenes will be a member of the Pittsburgh Pirates.

Ivan Brethowr, who the Pirates got by flipping the other part of the Hayes return, is a 22-year-old outfielder who was drafted in the seventh round last year, and who is hitting for a .710 OPS in High-A. He should go to the Greensboro Grasshoppers, and if he beats the odds, he’s another player who could arrive in Pittsburgh by the end of the decade.

The Pirates now have a defensive hole at third base for the remainder of the time they have Skenes. Their top pitching prospects in the minors will arrive without the help of Hayes at the hot corner. They could replace Hayes with Triolo, but the defense wouldn’t be as good and the offense would be similar, if not worse. The value Triolo has is that he’s less expensive. Like Kiner-Falefa, he’s more valuable as a utility player with good defense at multiple positions.

At best, the Pirates cut salary long-term, with the promise that they’ll actually focus on adding to the MLB roster with that money this offseason. And to my knowledge, they haven’t even said this will be the case. I’ve only seen Pirates reporters instantly speculating on that.

If you believe the Pirates are going to throw a switch and begin aggressively upgrading the Major League roster this offseason, while spending the money it would take to get an offensive upgrade at third base, then I would like to discuss an up-and-coming stock with you. It’s called Aerotyne International.

The Pirates, though, aren’t even Aerotyne.

The Pirates are not a cutting-edge baseball team in the Midwest, awaiting imminent payroll approval on the next generation of on-the-radar players that have both huge offensive and defensive applications.

They’re just a cheap baseball team in the Midwest, always selling you on prospects that are 3-4 years away, while promising that they’re six months away from spending money.

Build, Not Rebuild

When Ben Cherington was hired as the General Manager at the end of 2019, he inherited a team that was on the verge of a rebuild. His first move, a few months later, saw the trade of Starling Marte for Liover Peguero and Brennan Malone.

One of the things which always stood out to me was Cherington’s comment following the Marte trade that the Pirates were in a “build” and not a “rebuild”. His comments to Jason Mackey of the Post-Gazette in February 2020 make less sense over time.

“We’re not tearing something down to start over,” Cherington told the Post-Gazette. “We are simply taking a team that wasn’t good enough or wasn’t as good as we wanted to be last year, but has a group of players with a chance to be much better, and we’re trying to build on that.”
To make his point, Cherington brought up the Starling Marte trade, pointing out that it’s the only one he’s made to this point involving a major league player. He’s not wrong.
“If we had made four or five other trades involving more established major league players who were on last year’s team, then maybe I’d think about it differently,” Cherington said.

The Pirates didn’t have much of a chance to trade more than Marte. Cherington was hired late in the 2019-20 offseason. COVID-19 shut down the world a month after those comments from Mackey’s article, and the 2020 MLB season was shortened to 60 games. One of the highlights of that shortened season was the September debut of Ke’Bryan Hayes, which Hayes never replicated.

When Cherington took over, he inherited a minor league system that had Hayes on the verge of the Majors and Oneil Cruz in the upper levels. The 2019 season had also just seen the debuts of Bryan Reynolds and Mitch Keller.

The Pirates didn’t build upon that team. They didn’t add anyone of significance for the 2020 season, after immediately trading away their best player in Marte, which came before the above comments. I’ll get to what happened next, but I want to get back to that article from the Post-Gazette, with a credit to Mackey for being a conduit for Cherington, which allows us to go back and see the stated mindset at the time.

Cherington also came across as relatable and sympathetic whenever discussing how his aversion using the term “rebuilding” probably doesn’t sit well with fans.
“This is one where I can understand how honest, reasonable people might see it differently,” Cherington said. “But this is honestly how I see it. This is honestly how I feel. So it’s honestly how I’ve tried to answer the question.
“If I think about the word rebuild, what comes to my mind is a team that has been doing well that you are taking apart to then rebuild it, and you’re in the process of doing that. It feels more like where the Blue Jays were after 2016. We knew we were going to have to rebuild that roster. That’s what happened over the last couple years, and hopefully now they’re getting closer to being more competitive.”

Cherington joined Toronto’s front office in late 2016, and cited that team to Mackey as an example of a roster that qualified for the word “rebuild”. His explanation at the time was that the Pirates in 2020 weren’t coming off the success of Toronto in 2016, and thus weren’t in a similar “rebuild” situation. The problem with the statement is that Toronto didn’t actually rebuild immediately after 2016.

That 2016 Blue Jays team won 89 games and lost the ALCS. They were a contender at the deadline, as evident by the fact they traded promising up-and-coming pitcher Drew Hutchinson to the Pirates in exchange for Francisco Liriano, with the Pirates needing to send a few prospects to soften the blow of Liriano’s contract. I hope you can detect some sarcasm here.

Toronto didn’t exactly rebuild after 2016.

They did allow 33-year-old Edwin Encarnacion to walk as a free agent, but they retained 35-year-old Jose Bautista, 31-year-old Troy Tulowitzki, and 33-year-old Russell Martin each for at least one more season. Bautista was retained as a free agent. They signed 33-year-old Kendrys Morales as a free agent on November 18, 2016 to replace Encarnacion. Rebuilding teams don’t construct a roster of highly paid players in their 30s.

It’s more accurate to say that Toronto got worse after the 2016 season. They won 76 games in 2017, 73 in 2018, 67 in 2019, and returned to the playoffs by 2020.

The closest thing they had to a tear-down and rebuild was when they traded J.A. Happ, Seunghwan Oh, Roberto Osuna, John Axford, Aaron Loup, Josh Donaldson, Curtis Granderson, Aledmys Diaz, and Russell Martin between the trade deadline in 2018 and the start of the 2019 season.

Cherington took over the Pirates four years after their last playoff appearance, while trying to explain that the 2020 Pirates were in a build situation, compared to his misrepresentation of the timeline of the Blue Jays’ rebuild. Toronto might have been better off actually rebuilding following the 2016 season, but they waited two years after their last playoff appearance.

Going back to the Mackey article from 2020:

In Cherington’s mind, the parallel to draw there involves the Pirates’ three consecutive trips to the postseason from 2013-15. The players from those teams, aside from Gregory Polanco, are gone.
“I see a team that certainly had a good stretch from 2013-15, with largely a different cast of players at that point,” Cherington said. “If we look at 2019-20 and beyond, we’re not rebuilding something that was in place in 2019. We are just trying to keep building.
“A good chunk of players who were on the team last year will be on the team this year, and they really do have a chance to be part of that next winning team. We’re just trying to build toward that.”

Here are some of the players who the Pirates had when Cherington took over in late 2019, who he claimed to be building around — as players who had a chance to be part of the next winning team in Pittsburgh:

Josh Bell - Traded on 12/24/2020 for Wil Crowe and Eddy Yean
Joe Musgrove - Traded on 1/19/2021 for Hudson Head, David Bednar, Omar Cruz, and Endy Rodriguez
Jameson Taillon - Traded on 1/24/2021 for Maikol Escotto, Roansy Contreras, Canaan Smith-Njigba, and Miguel Yajure
Adam Frazier - Traded on 7/26/2021 for Michell Miliano, Tucupita Marcano, and Jack Suwinski
Clay Holmes - Traded on 7/26/2021 for Diego Castillo and Hoy Park
Richard Rodriguez - Traded on 7/30/2021 for Ricky DeVito and Bryse Wilson
Jacob Stallings - Traded on 11/29/2021 for Connor Scott, Kyle Nicolas, and Zach Thompson

Less than a year after Cherington went into detail about how the 2020 Pirates were a team about to enter a build, with the potential to add to the existing roster, he began trading every valuable player away in classic rebuild fashion. That rebuild took nearly a full year, and was completed almost two years after Cherington was hired to get the Pirates back to winning.

The average fan might look at the names returned to the Pirates in those deals and realize that very few made any kind of impact in the majors.

The best of the bunch was Bednar, who was traded to the New York Yankees hours before Thursday’s deadline. I’ll get to that deal later.

Jack Suwinski had a few good seasons, but has spent most of the last two years struggling in Triple-A.

The only players from that group who might be able to help the Pirates going forward are Endy Rodriguez and Kyle Nicolas, who have both seen their values decline due to injuries.

Cherington’s “build” was horrible, to say the least.

Most of the players he traded away still have value in the Majors in 2025-26. The one player who actually had a chance to be part of the next winning team in Pittsburgh was Frazier, who was one of the team’s big free agent signings this past offseason, and has already been traded after a poor season as a utility player. The problem there was the Pirates tried to contend in 2025 with an aging Frazier playing off the bench as one of their big offseason additions.

By the standards of Cherington’s comments in 2020, the Pirates in 2025 can’t even be considered a rebuild situation, as too much time has passed since the last winning season in Pittsburgh.

We are now a decade removed from the last playoff team in Pittsburgh, with Cherington overseeing the team for the majority of that time. The Pirates have had nine losing seasons since 2015, and six have been under Cherington — assuming there’s no miracle turnaround this year.

By Cherington’s own standards set in 2020, the Pirates are arguably in better position right now for a “build” and not a rebuild. The key quote, repeated, from 2020:

“We are simply taking a team that wasn’t good enough or wasn’t as good as we wanted to be last year, but has a group of players with a chance to be much better, and we’re trying to build on that.”

Regardless of the word you want to use, the most accurate thing you can say about this deadline is that Cherington is rebuilding his own rebuild.

This time, he’s not trading players he inherited whose performance got the previous General Manager fired.

This time, he’s trading the prospects he inherited, along with the few good players he got from his last rebuild.

And this time, he’s got the chance to build around the best pitcher in the game, despite continuing to show no urgency to add to the Pirates in the two seasons that Skenes has been in the Majors.

The David Bednar Trade

I want to take a moment to point out something about the David Bednar deal with the Yankees.

The main return of the deal was catcher Rafael Flores, who turns 25 this offseason, and has played ten games in Triple-A. His offensive results in Double-A included an .841 OPS in 370 plate appearances this year, with 15 homers. MLB Pipeline ranks him as the number eight prospect in the Yankees system.

From what I’ve seen, the projected scouting upside isn’t great from Flores. He’s not a top 100 prospect, and it’s disappointing the Pirates couldn’t get that level of return for an elite closer. Flores has struggled in his limited run at Triple-A, and the scouting grades make him sound like he’s got less future value than Henry Davis or Joey Bart.

Flores wasn’t the only catcher in the deal.

The Pirates also added 19-year-old Edgleen Perez, who is hitting for a .604 OPS in Single-A this year, and was MLB Pipeline’s number 14 prospect in the Yankees system. He’s another addition to the 2025 Bradenton Marauders, with hopes that he can beat the odds that are stacked against every minor league player and arrive in the Majors one day. Just like Stafura in the Hayes return, if we see Perez, it won’t be until 2028-29 at the earliest.

Brian Sanchez is the third prospect in the deal, a 21-year-old outfielder who has an .811 OPS in Single-A, and wasn’t in MLB Pipeline’s Yankees top 30. Once again, the Bradenton Marauders get a player this year, and Pirates fans have another prospect to dream upon in hopes the team could win later this decade, after Skenes is gone.

I’m going to point out that Bednar’s value was somewhat limited, due to having only one year of control remaining beyond the 2025 season. The best player acquired from the first Cherington rebuild, Bednar’s legacy with the Pirates was largely being a hometown hero closer across four losing seasons.

The Pirates couldn’t trade him in 2023 to maximize his value, similar to what the Athletics did at this deadline with Mason Miller, because the Pirates were still in the process of selling hope that their first rebuild was heading in the right direction.

What I wanted to point out from this trade is the similarity to that first rebuild: The focus on catchers.

With the first overall pick in the 2021 MLB draft, the Pirates selected Henry Davis as a potential franchise catcher.

Davis was an under-slot pick, which allowed the Pirates to sign Bubba Chandler and other prep players. I would argue they could have had Chandler if they drafted prep shortstop Jordan Lawlar, who was MLB Pipeline’s number 11 prospect in baseball heading into this season, and who is eight games into his MLB career in 2025.

The Pirates don’t have any elite hitting prospects on the doorstep to help the big league club, which is a negative result from their attempts to improve the development system. The first rebuild might have looked different if they had taken Lawlar and had one of the game’s top prospects set to arrive right around now. Instead, they went for Davis, who is one year older than Flores, as the centerpiece of their future winning plans.

Months before drafting Davis, the Pirates added Endy Rodriguez in a trade for one of their most valuable MLB pieces, Joe Musgrove, which is the same deal that brought Bednar. The Pirates had Musgrove to trade, and they had the first overall pick. They used that value to load up on catching prospects.

Now, they’re trading Bednar for multiple catching prospects, because the first group hasn’t worked out.

And if Cherington’s investments in catchers with power, or first baseman Spencer Horwitz, had worked out, the team might not have urgently needed offensive production from their defensive gem of a third baseman.

The worst part about Cherington rebuilding his own rebuild is that he’s rebuilding it in the exact same way the first one was built.

Why will this one turn out any different?

Other Trades and Acts of Complacency

Just before the deadline, the Pirates traded left-handed starter Bailey Falter to the Kansas City Royals. The return for Falter, who had three years of control remaining, was two prospects who weren’t in MLB Pipeline’s top 30 for the Royals.

Immediately after the trade, Noah Hiles of the Post-Gazette reported that a Pirates team source told him Falter was a non-tender candidate this offseason.

Falter was one of the best additions made by Cherington during his rebuild. The Pirates dealt infielder Rodolfo Castro to get Falter at the 2023 deadline. Over the last two seasons, Falter has combined for a 4.12 ERA in 255.2 innings in the Pirates’ rotation. He still has three years of team control remaining, and will be due a raise over his $2.2 million salary this year.

Castro was the type of prospect the Pirates typically pin their hopes on. With average upside at best, a more likely upside of a bench player, and the most likely outcome being Triple-A depth, the fact that the Pirates got a starter who could post league-average numbers for Castro was a clear win.

The two players in return for Falter are first baseman Callan Moss and left-handed pitcher Evan Sisk. Moss is a 21-year-old in High-A, with a .790 OPS and seven homers. He will likely report to the Greensboro Grasshoppers. Sisk is 28-years-old, with 5.1 innings in the Majors and horrible control. He will go to the Indianapolis Indians.

Best case, the Pirates fix the control of Sisk and repeat this process to get a cheap Major League lefty, while adding another name to the A-ball mix for 2028 and beyond. These seem to be the themes — saving money and loading up on long-shot lottery tickets for the future.

What is surprising is the Pirates didn’t trade three players on expiring contracts. Tommy Pham, Kiner-Falefa, and Andrew Heaney all remained with the team through the deadline. They also retained Dennis Santana, who will be arbitration eligible for one more season. If the Pirates tender him a contract, Santana will be due a raise over his $1.4 million salary this year.

That group of players combines to make $16.8 million this year. If the Pirates would have just salary dumped all of them for a live body in the lower levels, they could have saved enough money for nearly a full year of Hayes. Or, at the least, they would have had more than enough to cover any raise for Falter.

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A Rebuild That Makes The Pennsylvania Turnpike Construction Look Efficient

What is the hope for the Pirates?

Is it that Cherington might get a better return in his rebuild trades this time around? That might help in 2028.

Is it that after six seasons, Cherington will actually oversee an offseason which brings in quality players that show the team is making a serious effort to contend, rather than only adding bench players and value starters making $5 million or less?

Is it that after six years of picking in the top ten of the MLB draft, the Pirates will start to get more than an average second baseman and a backup catcher? I’m leaving Skenes out of this, as he was a lottery gift for the Pirates, and they are on record as saying they didn’t decide on that pick until 20 minutes before they selected first overall.

One of the few things you can say to hold hope from the last rebuild is that Liover Peguero — the main return from Cherington’s first trade, when he dealt the most valuable player from the 2019 Pirates roster — is only 24 years old and shouldn’t be written off just yet.

Maybe there’s some hope that the Pirates are two games under .500 with Don Kelly as their manager, after Cherington retained Derek Shelton through three last place finishes, two fourth place finishes, two 100-loss seasons, and a 12-26 start to the current season.

That only shows a continuation of the tendency for inaction from Cherington.

He started his tenure by delaying an obviously needed rebuild, finishing that process two years after he was hired. And he went out of his way to explain why the Pirates didn’t need to be immediately rebuilt, without doing anything to build upon that inherited roster.

He’s done nothing over the last two years to add to a team that now has one of the best young pitchers in the game.

Cherington loaded up on catching prospects in 2021, and is now loading up on catching prospects again in 2025 by trading the only positive value player he received in those 2021 trades.

He waited four years and two first overall picks before replacing the amateur scouting director who oversaw the draft.

He waited five years and tens of millions of dollars spent on the international scene before overhauling that scouting and development process which was producing zero results in the years before he arrived.

So if you’re holding out hope for Konnor Griffin — who is the top prospect in the game according to MLB Pipeline, and who was the first pick under the new scouting director — you’d have to ask why that scouting change wasn’t made sooner. And the reality is that Griffin is 19-years-old and in High-A, which means he won’t arrive in the Majors until 2027-2028 at the earliest.

If you’re holding out hope for Griffin, you’re admitting that the Pirates still have years to go before they might return to winning. And I honestly don’t think it’s fair to Griffin to put the team’s hopes of winning in the future on his young shoulders.

Research and Development

The one area where Cherington has made significant additions to the Pirates has been in the analytics department.

In a recent column at Pittsburgh Baseball Now, John Perrotto reported that Pirates owner Bob Nutting authorized $20 million in additional funds this year, which Cherington spent on analytics staff and technology, rather than players. This is not the first report of Cherington boosting the analytics department with his funds.

I wrote a thread about this topic on X last weekend, and you should read through that for my thoughts on Cherington’s choice of how to spend his budget.

Some of the biggest offseason moves the Pirates have made the last few years have been to the analytics and research and development teams. During the 2023-24 offseason, they hired Sarah Gelles from the Houston Astros as Assistant General Manager, tasked with creating an R&D department for the Pirates.

This past offseason, the Pirates hired Kevin Tenenbaum to oversee that department. Noah Hiles wrote about this expansion earlier this year in the Post-Gazette. They also hired Mike Voltmer from the Los Angeles Dodgers as the Vice President of Pro Evaluation and Strategy.

It’s difficult to qualify the impact these roles can have, but it’s easy to see when there’s been no positive impact.

For example, this is a team that signed Tommy Pham as their big free agent over the offseason, and it took them two months of watching him struggle to realize he couldn’t even see. The Pirates clearly aren’t leading a revolution in finding and unlocking value.

Most of what Gelles was hired to do was to build something other teams already had. She’s repeating with the Pirates what she helped build in Houston and what she worked on with Baltimore in the last decade.

Way back in 2013-15, the Pirates were competitive in large part due to their ability to find value catchers. They added Russell Martin and Francisco Cervelli, leading their last winning efforts. This was at a time when Mike Fitzgerald led a small analytics approach.

Fitzgerald was hired away by the Arizona Diamondbacks after the 2016 season, and the Pirates have since struggled to find value at the Major League level. Cherington’s additions are replacing what the Pirates once lost, but he’s largely catching up to what teams were doing when the Pirates lost Fitzgerald, rather than creating something revolutionary.

It’s possible the Pirates are creating something revolutionary, and we just haven’t seen the results yet. You could pin your hopes on the idea that the players they just added are a product of this expanded analytics department. However, this requires a massive benefit of the doubt, with no early results to back it up, and delaying hope for several years.

Trade Deadline

I have to admit, I’m not very good at trading on the stock market.

Part of it is that I don’t have the capital to be successful. At the end of May, I identified an option for Advanced Micro Devices (AMD) stock. The option in particular was a $110 Call for August 15th. What this means is that I was predicting the stock price of AMD (around $110 at the time) to go up in price by August 15th. Right now, AMD is trading at $176.31, which would make that option worth over $6600. It was priced around $1000 at the time, but I didn’t have $1000 to put into an individual stock pick. I spent a career writing about the Pirates prospects.

I felt like the Pittsburgh Pirates. No funds to make the obvious good additions.

I have made some money, including a few lower cost AMD options — the equivalent of a $5 million free agent. The month of July is my third month trading, and the first month I’ve shown a positive return. However, it’s not enough to be a career. I’m not a playoff contender, so to speak. And it’s more stress than baseball writing. Even covering the Pirates.

This process, aside from giving me a new perspective from baseball reporting, has also given me more sympathy for the job that Ben Cherington holds, or that any General Manager would have in Pittsburgh. With the limited budget in Pittsburgh — part of that due to Bob Nutting’s risk tolerance and a bigger part due to MLB’s economic structure — I don’t think any General Manager could have success.

Having said that, part of what gave me hope about Cherington in 2019 was that he was an experienced General Manager. There wouldn’t necessarily be a learning curve that would lead to the need for an extended rebuild with risk of the team losing in the year 2025. If the Pirates were traded in options contracts, I would have predicted in 2019 that they would have been playoff contenders by 2025.

The job that Cherington has done has been disappointing by any standards.

His focus on building up the analytics staff makes sense, as MLB teams had been doing this before he was hired by the Pirates. There’s legitimate criticism about Nutting’s spending, but I question whether Nutting can possibly spend enough to compete with the spending of other MLB teams in the front office, along with getting the Pirates out of the bottom-five in MLB payroll.

Major League Baseball has some massive issues that will need to be resolved in the 2026 Collective Bargaining Agreement in order for baseball in Pittsburgh to survive.

Yet, even with that reality, there has been no sign of improvement from Cherington over his six seasons. Even a rookie General Manager learning on the job would be expected to show improvements by this point.

The minor league system is not producing, with even the results from the high valued draft picks of Cherington’s rebuild not working out at a standard rate.

Aside from Aroldis Chapman’s one year, $10.5 million deal, no addition in six years to the Major League team has moved the needle toward contending, without hoping for a massive surprise from a value free agent. Cherington hasn’t even signed an external player to a multi-year deal. It is possible that no one with talent wants to play in Pittsburgh.

There are questions about asset management. Cherington just retained three players who are on expiring contracts, in a losing season that started with the Pirates claiming they lost money in 2024. They did the same thing with Chapman, retaining his salary and failing to get anything in return from his value at last year’s trade deadline. For a team that followed up by claiming they lost money, they had an easy solution this time last year to save some dollars and add hope for the future.

Almost none of the trades made by Cherington have added any tangible future value, and the ones that worked out ended up with declining value in the long run. It was a win to get David Bednar in the Musgrove deal, but Bednar has now been traded for a return led by a catcher who projects to be a below-average starter at best. The addition of Bailey Falter was a shrewd move, but he was flipped for two lottery tickets when it came time to pay him more than $2 million.

The massive amount of spending on baseball development staff, while catching up with the rest of the league, has yet to produce a single player who gives evidence that the spending is bringing in any returns.

Worst of all, there’s been a trend of inaction in making improvements. As an experienced General Manager, with experience in another contending organization’s front office, Cherington should have known what this team needed to change within the first year.

It took two years to rebuild the team, and 4-5 years to rebuild the amateur scouting departments that are essential to small market success. Cherington didn’t even begin adding key pieces to his analytics and R&D initiative until four years into the job.

I don’t want to put all of this focus on Cherington, because Nutting is ultimately the guy in charge. The fact that Cherington was allowed to oversee another draft and another trade deadline, with no signs of improvement in six seasons, is a testament that the owner of the Pirates either doesn’t know what he’s overseeing, or doesn’t care about the on-field results.

The Pirates are a team with a dated organizational structure that has a Team President on the business side with more power than Cherington. The focus of president Travis Williams has been to upgrade the marketing department, while constantly emphasizing that fans really care more about having a good experience at PNC Park, with the insistence that this experience doesn’t include watching a winning team.

Currently, the Pirates are on pace for one of their lowest attendance totals at PNC Park, which no longer benefits from being one of the best new parks in the game, like it did when the Pirates were in the midst of a record losing streak in the early-aughts.

Fans turn to the Pirates for entertainment. The cost of living in America has gone up exponentially over the last five years, to the point that food costs are 25% higher and housing prices are out of control in most cities. If people do have extra money for entertainment, they’re looking for an escape. What the Pirates emphasize as their priority for visitors to PNC Park is basic customer service and business practices. The Pirates are expecting their customers to act like they’re going above and beyond by offering concession products customers might want to buy, and line management that doesn’t drag them away from the game for multiple innings.

My self-created job of writing about the prospects in the Pittsburgh Pirates’ organization is probably one of the most recession-proof jobs in the game, in theory. The Pirates are always going to be a team that relies on their minor league system, and selling hope for the future. If that future never arrives, fans become bitter. It should say something that I’ve opted for the stress of the stock markets over writing about this team daily.

Years ago, Pirates fans began giving up on this team. The attendance at PNC Park dropped below 1.5 million in 2018, which was the same year that I realized I could no longer afford to pay contributors to cover the minor leagues in every city, as Pirates fans were gradually giving up on the team by cancelling spending on any related product.

Last year, the team got a boost above 1.7 million, which might be due to the fact that fans could go to the park and watch one of the best young players in the game. In year two of Paul Skenes, the attendance figures have plummeted back to being on pace for below 1.5 million fans. The Pirates aren’t surrounding Skenes with anyone who would make the team competitive, and spending a few hundred dollars to eat hot dogs in a 25-year-old ballpark while being surrounded by boos directed at a losing team is not an enjoyable experience.

The most successful approach the Pirates have had to bring in fans this year has revolved around bobblehead giveaways with FOMO marketing techniques.

America is at a point right now where a lot of families are relying on credit to an alarming extent in order to deal with the rapidly rising cost of living. Why would people go into debt to support the Pirates when their owner staunchly refuses to take on a single penny of debt to provide an on-field product that would entertain the fans?

I feel bad for Cherington, even if I don’t think he’s doing a good job. Being the General Manager of the Pirates is probably the most challenging GM role in the entire league. If he’s replaced as a scapegoat to direct attention away from Nutting and Williams, I’ll feel bad for the replacement, while hoping for better results and more of an obvious and urgent effort to build a winner.

Ultimately, I feel bad for Pirates fans.

You turn to this team for an escape at the end of a day working for your survival. That escape is not meant to induce rage, nor is it meant to be centered around hoping for a better future three years from now which might be just as disappointing as the last ten times you were told that the future looks bright.

Pirates fans want to experience the joy and excitement of watching a winning team. They want to recapture that magic from the 2013 Wild Card Game, where the city unified to unwind and unleash their energy in support of a winning team — while being rewarded with euphoria and excitement.

That was 12 years ago.

Since that Wild Card Game, there have been very few moments where Pirates fans could pay to visit PNC Park and experience a good time. At best, they get to hold a toy that they were handed as they walked through the gates to watch their team lose.

That’s not just a reflection of Cherington’s performance.

That’s on Travis Williams for patronizing and borderline infantilizing Pirates fans with a gaslit version of what every fan really wants.

And ultimately, it’s on Bob Nutting for caring more about maintaining ownership of the team in his family for as long as possible, without considering the long legacy of fan dissatisfaction and abandonment resulting from his stewardship.