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Pirates Prospects in 2025: The Pittsburgh Pirates and the Business of Baseball

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I have five book projects I’m working on in 2025.

One of those projects is my first sci-fi/horror/spy novel, which has nothing to do with baseball.

In the summer of 2020, I gave myself five years to develop a novel universe about time travelers and vampires. That included a few years of listening to musical artists who were nothing like me, in order to create a diverse group of novel characters that won’t be a nerdy white guy. This summer is my hard deadline to begin writing.

That project will fulfill a lifelong goal of mine to write a novel. My storytelling style draws inspiration from Tom Clancy, Stephen King, J.J. Abrams, Quentin Tarantino, Stan Lee, and a few others. This project is going to be dark, with the first book I write being the darkest of the series. When I described the first chapter to someone last week, they were instantly terrified of the opening scenario.

Granted, that person wasn’t a fan of the Pittsburgh Pirates.

My novels might be closer to the vibe of Mister Rogers, compared to the opening scenario for the 2025 Pirates.

If you’re a Pirates fan, my other books this year are for you, with the first project detailed below.

THE PIRATES ARE STILL FAILING

I don’t have any desire to cover the Pittsburgh Pirates on a daily basis this year.

The organization, as it stands right now, is beyond a joke.

Their owner, Bob Nutting, does not have the financial risk profile to ever succeed in this small market in this league economy. Nutting won’t spend money until he has it in his possession, and even then, he won’t spend as much of that money as he would need to spend to maximize his chances. Part of the issue is that Major League Baseball has a severe inefficiency toward small market teams, but Nutting’s risk-averse style makes things more difficult for the Pirates to win.

Their team president, Travis Williams (no relation), has spent five years essentially gaslighting fans with the Pirates’ own research that says what their fans really want to see — and that doesn’t center around a focus on winning. Williams transferred the Pirates’ social media strategy from the media relations department to a refocused marketing department in 2020, while refusing to be interviewed by media for the first two years of his duration running the team. I personally have lost trust in the entire social media scene after seeing disturbing changes to the overall social environment during this time.

Their General Manager, Ben Cherington, has overseen five losing seasons with the Pirates, along with one of the lowest payrolls in the league. His conservative style, whether in free agency or at the trade deadline, is to wait until the last minute and accept whatever cheap lottery tickets are available. There’s been very little proactivity to improve the roster, even with generational pitcher Paul Skenes on the roster. There is also a disturbing trend where Cherington’s additions almost overwhelmingly are people he’s worked with earlier in his career. This severely reduces the available talent pool for the team to Cherington’s personal rolodex.

Last summer, I wrote an article saying the Pirates were failing, from Bob Nutting to the Dominican Academy. It was, and still is my opinion that the Pirates won’t succeed with this front office and their approach toward winning. A lot of that is on the ownership. Nothing in the half-year since that article — including Cherington’s offseason moves, the front office comments at PirateFest, or the start of Spring Training — has changed my view.

When that article was published last summer, I had been discussing for months the hitting woes under then-hitting coach Andy Haines. Those issues were present before the season, and they were clearly holding the Pirates back from contending early in the season.

Cherington waited until after the season to make a change, and the hiring of new hitting coach Matt Hague seems to be the team’s biggest offseason addition. If Hague does upgrade the internal roster, that would obviously be great, though it would simultaneously raise questions as to why there wasn’t urgency to make a switch last season.

The big offseason player addition was the trade for first baseman Spencer Horwitz. The 27-year-old has 425 plate appearances in the majors, with some promising results in a small sample size last season. Horwitz is not a bad lottery ticket, and for a rebuilding team, he’d be a great option. The Pirates have the best young pitcher in the game, and have been sitting at 76 wins for the last two seasons. Horwitz shouldn’t be this team’s big addition.

What’s worse about the situation is the Pirates are repeating a mistake from last season.

The Pirates saw Rowdy Tellez put up the worst numbers in baseball across the first two months of the 2024 season. They stuck with him, while fans attached their hope to minor league veterans like Jake Lamb and Seth Beer. By the start of June, Tellez sought outside help, moving away from the guidance of Haines. He had a few great months, but faded down the stretch, and was released at the end of the year — four plate appearances shy of a $200,000 performance bonus.

One year later, the Pirates went with a cheaper lottery ticket in Horwitz. On Wednesday, during the first day of Spring Training workouts, it was announced that Horwitz would be out most of spring with a wrist injury, with Cherington saying he knew that Horwitz had symptoms of wrist issues at the time of the trade. The injury was described as something that happened after the trade, separate from the previous issue to the same wrist.

One year after the Pirates went through a summer of ups and downs at the biggest offensive position on the field, and one year after their fans were forced to look to minor league veterans and unproven players for hope, the Pirates are now entering Spring Training putting their hopes on Jared Triolo and…

Hold on, I honestly need to look up the names…

Darick Hall and DJ Stewart.

This situation at first base is currently akin to waving the white flag on the 2025 season in early February. That’s especially the case when the trio is keeping the seat warm for an unproven Horwitz.

Hall is in his age 29/30 season, after an OPS just above .700 in Triple-A last year. He had an .804 OPS in a small sample in the Majors at the age of 26, but has yet to repeat that success in the years since.

For anyone banking on the small sample of success from Horwitz at 26-years-old, there is no better disclaimer for reserved projections than his potential replacement in Hall.

Stewart has over 1,000 plate appearances in the Majors, with a .729 OPS. He can put up an .800 or higher OPS in a season, but his production typically comes as a bench outfielder.

Triolo would be great, defensively, but lacks power from his tall frame. This comes from a reactive, contact-focused approach at the plate. The same mindset and reactions that make him so great defensively are what hold him back from tilting into his larger frame for power at the plate.

The most intriguing internal option would be Billy Cook, who was acquired by the Pirates last year at the deadline. Cook is in his age 26 season, and unproven, so he merely adds to the depth of intriguing options.

Horwitz could be back in early April. He comes with questions about his productivity over a larger sample size, and now increased questions about his health and durability. The appeal is the classic “if he does work out, the Pirates have him for five years of cheap control” — with the caveat that “if he does work out” is the most important and hardest part of that dream. “If he does work out” is also not something you want to be saying about the team’s biggest offseason addition at this stage in their rebuild.

Last year, I wrote that the Pirates were failing, in large part due to their lack of urgency to make the moves necessary to contend.

The move they needed to make, in order to save last season before it got out of hand, was replacing their hitting coach. They didn’t make that move until the offseason.

They spent most of 2024 with a question mark at first base, and journeymen with non-starter upside as their replacement hopes in the minors. This year, they’re already relying on the journeymen, before position players have even reported.

And who knows how long they’ll stick with Horwitz if he’s struggling? Especially with his years of control, and the leeway he will be given following his wrist surgery. The Pirates traded Luis Ortiz and two prospects to get him, so Horwitz would likely get a longer leash than Tellez. And Tellez had a leash that ran right up until the Pirates had to pay him for continued service.

If you’re a Pirates fan, there is genuinely a lot to be optimistic about on the team-level for the 2025 Pittsburgh Pirates.

They’ve got Paul Skenes.

You could get optimistic about the upside of Oneil Cruz in center; the health of Ke’Bryan Hayes; or the young group of second base options led by Nick Gonzales and Nick Yorke.

The rotation, even without Ortiz, is a bright spot, with several more top prospects slated to join Skenes this year.

All of that excitement fades when you realize that no urgency toward winning has been shown by this front office and ownership group.

Winning attitudes start at the top. If the Pirates’ offseason reflected the winning attitude from the front office, the trickle down to the team level doesn’t seem like it will be dripping with optimism for 2025.

This front office still focuses heavily on telling fans that they really do prioritize winning, rather than showing fans one bit of action or sense of proactive urgency over the last five years to back up that statement.

And their owner is the definition of cheap, due to his extreme aversion to risk.

BUSINESS OF BASEBALL (B.o.B.)

My plan was to begin writing for the 2025 season on the first day of Spring Training.

I have several recurring features that I want to write this year, with a few of those working toward book projects.

When I woke up on Wednesday morning, I had little desire to begin the content schedule I’ve laid out for the 2025 season. The lone desire I had was for a single project: B.o.B.

I didn’t go to school for journalism. I have a business degree, and have been studying and simulating businesses since the age of 13. Most of that time has included a deep study into the Business of Baseball, with a college course on the economics of sports. Then, there’s my 18-year history as a sports writer, with 16 of those years focused on the business of baseball from a small market perspective on this site. In that time, I’ve learned a few things about journalism.

The Pirates haven’t generated much excitement for their upcoming season. I wouldn’t be surprised if they make a late addition over the next month, as the economics of the game this year have led to a slower free agency period. This offseason reminds me of slower years like 2016, when the Pirates made their most significant additions in February and March.

By the start of this season, I’ll be writing about the minor leaguers in the system, the 2025 outlook of the Major League team, and a few other fun topics I’ve got planned.

Last night, I decided that I didn’t want to proceed into any discussion about the 2025 Pittsburgh Pirates until I completed my first featured subject this year: Business of Baseball.

My original plan was to run the B.o.B. feature every Thursday during the 2025 season, as part of a larger content schedule.

I don’t have plans for live coverage this year.

Live coverage costs money, and as I pointed out in TWOWAADOS, I’ve had a long history of paying to create unique content, only for that content to be instantly replicated or stolen by the Pittsburgh media.

My plan this year largely involves writing from my knowledge and research, and because the Pirates have nothing exciting going on at the moment, I’m skipping Spring Training coverage this year.

In place of those 2025 Spring Training articles will be the B.o.B. project.

This project is meant to look at the economics of Major League Baseball, from a small market perspective. Obviously that perspective will be heavily focused on the Pirates. This project will take the deepest dive possible into the full operations of the Pittsburgh Pirates, and how they compare to other teams around the game.

I’ll be publishing my research on Pirates Prospects, daily throughout Spring Training. I’m also going to have a few articles where I combine the research into a column for better perspective and understanding.

At the end of my research and writing, my intention is to compile all of this information into a book, which will explain the MLB economic scene in full.

The goal with B.o.B. is not to individually condemn Pirates owner Bob Nutting.

At the outset, I’m going to let you know that there will be times where it looks like I’m defending Bob Nutting during this project. There will also be times where he looks like the Scrooge McDuck villain. I don’t think he’s an evil guy by any means, and I’ve heard repeatedly that he treats his people well. The purpose of this project isn’t to put Nutting on trial, but to describe that aversion to risk that I often speak about.

The goal of this project is for you to get an accurate layout of the entire MLB economic landscape, so that you know exactly where Nutting is being cheap, and where Major League Baseball makes it nearly impossible to contend, even if Nutting wasn’t cheap.

Check back every day throughout Spring Training for updates on this project.

PIRATES PROSPECTS IN 2025

I have three other baseball-related book projects that I’ll be working on throughout the year, in addition to the sci-fi/horror novel. Those other baseball books will be reserved for weekly articles throughout the season, and I’ll announce the topics later.

Here’s an early preview of what to expect this year:

  • One of my features is going to be more of a thesis in the field of performance psychology — which means the writing topics will range beyond baseball players and athletic performers.
  • There will be at least two days per week where I keep you updated on what is happening in the minor league system.
  • There will be at least one column about the 2025 Pirates each week, and there will be a weekly First Pitch, which is going to be a grab bag of recent topics and organizational results.
  • Aside from the book projects, I have some behind-the-scenes upgrades for the site, and you won’t be able to miss those updates when they arrive.
  • Because of my focus on site upgrades and larger book projects, I’m not going to be providing daily updates on the season as this site has done in the past.
  • This site is going to be treated more like a magazine than a newspaper. You won’t come here to find five different 350-500 word updates per day, but instead, a single long-form article.

At the end of my B.o.B. project this spring, I’m going to announce more details of the site’s in-season coverage.

SUPPORTING PIRATES PROSPECTS

I am just one person.

You might think to compare me with writers at bigger outlets, but those writers only have to focus on creating content. The reality of this site’s 16-year history is that creating content has been, at-most, 40% of my job.

There are costs to keep this site running, which need to be paid before I make any money. This site is constantly under threat of attack, especially around MLB draft and trade deadline time, when Pirates fans are more likely to be reading opinions, and when this site gets the most historical DDoS attacks to slow it down or knock it offline.

I own this site, 100%, with no investors or co-owners. In the age of angel investors and venture capitalist dreams, what I’m doing is extremely rare, and extremely difficult.

This year, I’m going to be putting some money into site upgrades that will prepare the site for the next phase of the internet.

From there, you are paying for my survival, while I try to produce daily baseball content to give you an escape. You’re also paying for my work and time dedicated toward serving Pirates fans such as yourself with unparalleled understanding of deeply complex subjects surrounding the team.

You’re also paying to provide real accountability to Bob Nutting.

On October 12th last year, Dejan Kovacevic announced a plan to provide similar accountability to the Pirates on his site. Their original plan had Connor Williams (no relation) from Bucs Dugout set up to do the research into operations, although those plans fell through when Williams and Kovacevic had a public falling out.

In that article, Kovacevic discusses how his day-one silent investor, Chris Hylen, was footing half of the bill for this coverage. Hylen’s intent, as described by Kovacevic, was to create a book from the writing of Connor Williams and others, while launching a campaign to raise money under potential phrases like “Sell The Team” or “Our Team Not His.”

One week later, Kovacevic reported on a new billboard campaign that started under the site OurTeamNotHis.com, with “Sell The Team” phrasing.

There has never been mention of Hylen being attached to this specific project, despite Kovacevic describing an almost identical plan from Hylen a week earlier. The plans for articles to study the Pirates operations have gone silent since the billboard campaigns began. The billboards have been covered by DKPittsburghSports more than any other outlet.

The billboards have raised over $31,000, which has gone to five locations around Pittsburgh. Two of those locations are on land owned by the city of Pittsburgh. Two of those locations are on land owned by Lamar Advertising, which handles the advertisements for this campaign. The final billboard is in a parking lot attached to Rosen Capital. All of that information was gained through public land ownership searches, and doesn’t suggest a connection to the billboard campaign.

From my research, the biggest thing this campaign has accomplished is driving tens of thousands of dollars into the city of Pittsburgh’s economy, through the local advertising industry. That’s not counting the shirts being sold by Pittsburgh Clothing Company. I don’t know of any affiliation between Kovacevic, Hylen, DKPittsburghSports.com and the billboard campaign.

These billboards will not change a thing with the Pirates ownership.

They’re just repeating a message that has been shouted on social media every day for years.

What might bring some change is a research project that details the obvious flaws in this system. The change I would like to see is not a forcing of Nutting to sell the team, but Major League Baseball creating a fair economic system in the next CBA discussions. In this project, I’ll detail how difficult that systemic overhaul would be for the league.

If you’d like to support this site and the B.o.B. project, there are three ways:

  1. Become a Patreon member. Your support helps keep this site fully independent.
  2. Read the site daily without an ad blocker, so that I get paid by the advertisements.
  3. Buy the books when they are released. The books won’t be available for ordering until they’re completed and printed.

This is the 17th MLB season that I’m running this site, with a combined 3.5 years of running a solo operation. This has always been a fully independent site, thanks to massive user support.

Your support this year will allow me to dive into the subject that got me into sports writing in the first place. I’m not doing this to sell t-shirts, and I’m producing a book only to compile the information together in the best way.

In the end, maybe Pirates fans will have more effective talking points than “Sell the Team.”

Tim Williams
Tim Williams
Tim is the owner, producer, editor, and lead writer of PiratesProspects.com. He has been running Pirates Prospects since 2009, becoming the first new media reporter and outlet covering the Pirates at the MLB level in 2011 and 2012. His work can also be found in Baseball America, where he has been a contributor since 2014 and the Pirates' correspondent since 2019.

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