There’s a reason that I’m still here.

It’s not entirely money.

We all need to make a living in this Capitalistic hellscape, and I’m very fortunate that I’ve been able to make a living for a long time writing about sports without a boss. It’s allowed me to write in a way that I never could if I worked for anyone else. To be honest, this site gives me the chance to be the highest paid baseball writer in Pittsburgh — though I don’t care about money, so I take what I need and tend to spend the excess on more writers for the site.

I became a sports writer at age 23, and started this site at age 25. Sports — not just baseball — was a huge part of my life.

I’m now 39, and if I’m honest, I can’t remember the last sporting event I watched. That includes baseball, where my work on this site has transitioned to more of an editor role since covering games in early September, and less the main analyst covering the team for this site.

If I left this site today, there would probably be a long period of time where I didn’t have anything to do with the game of baseball before I could get back in it again.

A big credit there goes to what Rob Manfred and the MLB owners have done to this game to decimate the small market fan experience.

It’s not that I don’t love the game of baseball. I would love to love the game of baseball again.

To be completely honest, the current state of Major League Baseball makes it difficult to enjoy the sport in the traditional way — you know, cheering for one team to win a World Series year after year.

If the Pirates eventually win a World Series, it would be cool to cover and write about. It would also do nothing to advance my personal life, other than to make me happy that so many Pirates fans I know are happy (along with the players and personnel who achieved the success).

I think the game of baseball, and all sports, provide us with the chance to project ourselves out into the world and live vicariously through a bigger entity that can only reflect our lives, but not impact it in a serious way. Sports are a simulation.

It can be extremely frustrating when you are looking for this escape in life — pinning your hopes for momentary happiness on something bigger than yourself — only to have that escape be just as frustrating as real life.

Or, sometimes for Pirates fans, the escape can be worse.

PROVIDING AN ESCAPE

There’s a reason that I’m still here.

It won’t bring me excessive joy when the Pirates win a World Series, but I know that there are a lot of people who read this site who will experience a once-in-a-lifetime joy when that happens because they’ve invested so much time into this organization. Their joy will bring me excessive joy.

Until then, one of the things I’ve realized in recent years is how many people rely on this site and other Pirates sites just to get through the day/week/month/year.

I’ve appreciated how many people use this site to escape their daily lives, but also to connect with Pirates fans all over the world over a shared interest: Dreaming of a future where the Pirates are once again World Series champions.

It’s difficult to imagine that future right now.

The Pirates have been one of the worst teams in baseball the last few seasons, and while things look to be changing, it’s not like flipping a switch. The Pirates will likely lose in 2023. They could trade one of their best players in Bryan Reynolds, and that could happen this week. It’s difficult to see the light at the end of the tunnel right now, and I don’t blame skeptical fans for questioning whether there is a light at all.

For the last two seasons, I’ve been building up this site’s content plan to what you see today — which still isn’t where I want it to be, but is a content plan I’m proud to produce. If you love what you’ve seen, please smash that “Contribute” button to keep our efforts going!

I’ve also been watching closely what the Pirates have been doing in their farm system and organization, to see if there are actual changes being made that will lead to a World Series.

ARE THE PIRATES REALLY CHANGING?

There’s a reason that I’m still here.

I think the Pirates are doing something really special right now.

It’s difficult to describe what that is, especially without results to back it up. It’s easy for me to see the differences, because I practically lived at Pirate City for a decade.

It took me one conversation with Mike Burrows to see how much things had changed.

I only needed to watch Endy Rodriguez play on the field once — and I’m talking a year before his breakout 2022 season — to see how the organization had shifted.

Anyone who read this site from 2009-2019 knows that I respected the hell out of Neal Huntington and the job he did, even if I was very critical of his direction in the final years. Despite that, he left the organization in amazing condition for Ben Cherington to do what he’s been doing.

It didn’t take me many conversations with Cherington to realize that what he’s been doing the last few years is building a bigger, modern-day organization.

Neal Huntington was trying to win after 2015 with a classic baseball organization. You’ve got your General Manager, who reports to the team president, who reports to the owner. There are a few other department leaders, but the entire operation seems small compared to what we see in corporate America today.

My read on the situation is that Cherington is in complete control of the baseball side, with President Travis Williams only focusing on making the Pirates money. This is a shift from Frank Coonelly, who had oversight of Huntington’s moves, and that was a negative.

Cherington is modeling modern organizations with endless compartmentalization that allows organizations to isolate and perfect every single facet that leads to success.

The biggest thing that hampered Huntington in the end, in my opinion from seeing things closer than anyone on the outside, was that he was trying to win consistently with an organization that wasn’t big enough to sustain both winning now and winning later.

Perhaps just as equally important, their approach toward the players and personnel was bad, with too much oversight, and too little automation from each individual departments.

Ben Cherington has been building a bigger organization, but also one that isn’t run on micromanagement, and one that treats employees better.

Ben Cherington’s Past, Present, and Future

When the Pirates hired Ben Cherington, I was skeptical, but optimistic.

I was optimistic, because Cherington has won a World Series.

Granted, that came in the large baseball market of Boston, where there are more resources to work with than in Pittsburgh. Cherington did win using methods to find value — most notably finding value in mid-tier free agents. That focus on value will play in any MLB market, including a Pittsburgh market where Bob Nutting is the owner.

Cherington took over a Red Sox organization that needed a shift from a relaxed, and almost non-caring attitude toward the game. Starting pitchers were playing video games, drinking beer, and eating fried chicken in the clubhouse on non-start days — this is the most commonly described microcosm of the problem.

Cherington unloaded a lot of big contracts in his first year in 2012, then brought in an all-grit team of guys like Shane Victorino, Mike Napoli, Jonny Gomes, Stephen Drew, Koji Uehara, and other players who positively impacted the clubhouse atmosphere to a 2013 World Series.

After finishing last place in the AL East over the following two seasons, the Red Sox brought in Dave Dombrowski to oversee Cherington. This was during a period when MLB teams were starting to shift to bigger organizations, which typically include a President of Baseball Operations overseeing a General Manager. One focuses on the big picture, while the other focuses on the day-to-day to carry out the big picture.

Cherington resigned and left the game briefly, rather than working in the reduced role. What really stood out to me was that he became a professor at Columbia, teaching a course on Leadership and Personnel Management in the Sports Industry. You can read more about this in Stephen Nesbit’s outstanding article in The Athletic from January 2020. A lot of the raw honesty from Cherington and about him in this article is what initially sold me, as I was going through my own self-exploration at the time, trying to find the ways I had mismanaged my own company, and identified with a lot of what was expressed.

In his course at Columbia, Cherington assigned a few books from his personal library to students, including “Work Rules!” by Laszlo Bock, which details the workplace atmosphere in Google. Cherington cited it as the “evolution of how (a company) tries to hire and develop people and innovate.”

I haven’t finished reading Work Rules!, but everything I read reflects what I’ve seen implemented in the Pirates’ organization under Cherington. The biggest impact is how he’s given autonomy to each department head. This means that John Baker as farm director has more control over his department than Larry Broadway or Kyle Stark previously had in their roles under Huntington.

Baker is one of the people I’ve talked to the most the last two years, and is a big reason why I feel the Pirates are heading in the right direction from a development standpoint. That autonomy that Cherington is giving to department leaders is being passed down throughout the organization.

Baker has created a development system where the players are in control of their development course, and where the organization’s role is providing support in as many ways as possible, to maximize the chance that one of those ways will click. He’s also put more of a focus on developing coaches and giving support to managers.

The old organization was building toward this total collaborative nature, but needed a shift in attitude.

The old development system was widely seen and described as “militaristic”. This basically stems from the Navy SEALs training they had their players undergo in 2012. That training was optional, but the Pirates had a culture at the time that tacitly made it known that nothing was really optional if you wanted to advance your career.

I use the term “militaristic”, because for years I saw coaches acting like drill sergeants. I saw coaches with stop watches, telling hitters they only had 15 seconds of batting practice remaining before they had to run in cleats to the next practice station to maintain the all-important schedule. I can’t imagine those players were learning anything in those final swings. I saw, on a few occasions, coaches absolutely dressing down players in public.

I once stood five feet away as a minor league manager screamed at a pitcher on a bench in a public area, with fans standing and walking in the area. Now, the rules that are posted say that I can’t report on anything said outside of an interview, which allows everyone to operate in their work space in a comfortable way. I can tell you that this wasn’t comfortable, even to be around.

That player was eventually released. I couldn’t have even posted an article about the incident, because it would have inevitably led to someone commenting that the player deserved it due to his ERA in rookie ball. But, can you imagine ever building the confidence to be good on the mound after you’ve been chewed out in front of random fans and a credentialed reporter?

The manager was a mixed bag, and treated at least one of my writers like shit on one occasion. I never had an issue with this particular manager, but had incidents of my own with other development personnel. I also had a lot of good experiences with good people who worked for the organization then, and a lot of them still work for the organization. When I saw who Cherington retained, it was telling.

Overall, my experience with the old development group was positive, and I think Huntington, Stark, Broadway, and everyone else involved did important things that Baker is building upon today. A lot of what Baker is doing was expressed in a blog post he did for Gabe Kapler’s site back in 2015, if you want further insight into Baker’s mindset. I’m sure things have shifted, but the general concept of individualized approaches remains strong.

There was a thread of insecurity that ran through the old development system, and with that insecurity came an almost abusive streak toward anyone who was deemed less and who had the gall to challenge authority. In my experience, people who view themselves as above others for whatever reason, and who use that status to punch down on people they see as deserving of that treatment, are ultimately just insecure with their position.

And I’m sad to say that I’m saying this as an insecure person in recovery, who feels for all of the people still infected, and hates that I was once insecure and punching down like so many in this world.

What I’ve seen from Baker is the establishment of a system that will allow players to gain individual security in who they are as players and that what they can do on the field is enough, but always capable of improvement under a growth mindset. This system is meant to build confidence, by allowing people to succeed as themselves.

When a player gets drafted, I tell you what I think he could be on draft day — based on what scouts think he could be and based on his physical skills and stats at a meaningless level. This doesn’t mean the player sees himself in that same way inside his head.

It’s hard to be yourself when you know there’s the fear of retribution from a random amateur drill sergeant who might be having a bad day, and might want to take it out on your individuality.

Fortunately, that insecurity has been largely removed from this development system. Being around teams now, under the new group, is like a breath of fresh air.

When Mike Burrows told me last year in Greensboro just how much the old group negatively impacted him, I was shocked simply to hear a Pirates prospect emboldened to speak as an adult and say that his career had been negatively impacted by the direction of the organization. No one in the old system would have been able to speak so openly. Burrows was speaking about people and a process that weren’t in the organization any longer, but he was speaking with more confidence than you’d hear an A-ball player express in the past.

When I saw Endy Rodriguez and the entire 2021 Bradenton team celebrating in the dugout and showing emotion on the field, it reminded me of my trip to the Pirates’ Dominican facility in 2015.

There, I saw the most lively, animated, exciting baseball I had seen in the Pirates’ system. When I returned to the boring, “militaristic” approach with the US affiliates, I asked around why Latin American players didn’t show emotion outside of the DSL.

The answer I got from Latin American players? They were told that this wasn’t how professional baseball was played.

In a way, the Pirates played themselves by turning a game into something bigger. To put it in development terminology: “They were trying to do too much.”

They removed the fun for the players, but then also removed any sense of autonomy in the development process to allow for a sense of personal comfort. I might be more of a weed-smoking-artist-hippy, but that isn’t the type of organization I would ever work for, as I would never have success in such an environment. And I’m someone who has had over a decade of success in the booming field of journalism.

It makes me wonder if someone like Rodriguez — one of the most animated and charismatic players I’ve seen on the field — would have had this same level of success in a more restrictive environment. It makes me wonder how many of those players in the Dominican in 2015 might have gone on to the majors — I don’t think a single one did. We already know that Burrows wasn’t performing well under the old group, because he explicitly explained why, before becoming a top prospect in the organization.

These are two cases that give me optimism that the Pirates have solved their development issues. Almost.

They still need to change the culture in Pittsburgh, so that these players can maintain this growth mindset vibe into the big league clubhouse. That will need to change internally before the fans fully start to notice the change externally — though based on our traffic numbers lately, fans are starting to notice.

It seems to me that Cherington is currently taking a page out of his Boston playbook. He’s already brought in Carlos Santana and Ji-Man Choi. I wouldn’t be surprised if we see an influx of veterans added to this team, creating the pillars of the MLB atmosphere that Cherington wants to establish — right at a crucial time when so many young players are entering the majors.

We’ve already seen why that is important. Bryan Reynolds is currently disgruntled. He wants a trade, and the Pirates say they want to build around him.

It would not surprise me if Reynolds just can’t see the change yet. The Pirates haven’t cared much about the area where he’s been playing the last three seasons. They’ve been doing great things to grow their organization to a modern-day MLB organization, but the MLB team in Pittsburgh has been treated like MLB Extended Spring Training, to say the least.

For Reynolds to see the change, he would need to see more than just Santana and Choi added. He would need to see a true influx of talent into Pittsburgh, and not from the farm system. Veterans who know how to win. This is a good time to remind you that, while Reynolds is a great player, he’s mostly only played on the worst team in baseball. He needs to be led just as much as Endy Rodriguez.

I could see the Pirates trying to keep Reynolds, adding around him, and hoping that he has a change in heart when he sees more of their plan. I could also see them trading him this week while his value is high. We’re still in the point where their direction hasn’t become fully obvious to outsiders. It’s just becoming easier to see where the Pirates might be going.

Regardless of whether Reynolds is on the team in 2023, I expect Cherington to start adding to the majors this offseason. That’s not based on any inside knowledge, but based on what I see unfolding based on Cherington’s history, and what I’ve seen with how he’s been building this organization from the ground up.

They also have a plethora of prospects who are about to make the jump to Pittsburgh, who could push them to contending status sooner, than later, with the right MLB atmosphere in place.

There’s a reason that I’m still here.

I think the Pirates are heading in the right direction to have a real chance to win a World Series.

And as someone who felt the press box shaking during the 2013 Wild Card Game — the loudest event I’ve ever been to, concerts included — I want to be there when Pittsburgh celebrates a World Series.

LAST WEEK ON PIRATES PROSPECTS

I’ve been adjusting the amount of articles in Tuesday’s article drops. With all of the moves happening, and with my focus split right now between producing the site and finalizing the Prospect Guide, we’re going with a reduced schedule.

**Last week, I wrote about how the removal of defensive shifts might impact left-handed hitters at the plate.

**I also looked at how Carlos Santana gives the Pirates infield defense an important, yet subtle, upgrade.

**Anthony Murphy looked at Braxton Ashcraft, the 2018 second rounder who is returning from Tommy John surgery.

**We post our columns every Wednesday. This week, Wilbur Miller gave an early look at the top prospects at each affiliate in 2023. Meanwhile, I broke the space/time continuum.

**In last week’s Roundtable, we looked at whether the Pirates can have a winning season in 2023. Want to save yourself 2000 words of reading? The short answer from six writers: They can’t win in 2023. But, check out the article to read exactly why, and how they might be trending behind the losses. It’s my favorite article from last week, and a lot happened to bury it over the weekend.

**In Friday’s Pirates Discussion, Jeff Reed wrote about how there has been a refreshing change of pace. Of course, a day later the Reynolds rumors began.

**John Dreker wrote about the rough start this winter for Rodolfo Castro, and recapped the rest of the Pirates in winter ball in this week’s Pirates Winter Report.

**Ethan Hullihen wrapped up the week with a look at the history of Pirates Rule 5 selections.

**If you missed last week’s First Pitch, I dove into my view of the Pittsburgh Pirates universe. If you are wondering where the space and time travel writing comes from, check the Fuquay Vinyl section below.

THIS WEEK ON PIRATES PROSPECTS

I would expect the Pirates to be busy this week, and we’ll be busy covering all of the news and rumors that come out of the MLB Winter Meetings.

On Tuesday, we’ll have a smaller article drop, with some appropriate topics to read during the downtime from rumors.

I’ve got a Rule 5 themed column on Wednesday. Our Roundtable on Thursday will give our breakdown of whatever happens at the meetings.

Though the meetings end on Wednesday, I would expect the entire week to be busy. Check back each night for Pirates Prospects Daily to get the recap of everything that took place each day.

SUPPORT OUR WORK

Pirates Prospects has always been fueled 100% by reader support — whether through a high traffic site that relied on ads, or a full paywall that was supported by over 10,000 subscribers between 2015-2022. With no more paywall, the site is free for everyone. All I ask is that you Contribute at some point in the future to help support our work. We’re not going to impose any pricing limits, content restrictions, or timelines on anyone. We just hope that you enjoy the site and check back often!

FUQUAY VINYL PLAYLIST

What is Fuquay Vinyl?

At some point in 2020, I had a plan to open a record store in Fuquay-Varina, North Carolina. That got to the point where I had a wholesale account to buy records from the same distributor that supplies 98% of record stores. The plan involved me running this site from that store as I do now, but making my income from that store so that all of the money this site generates could allow it to grow to maximum effect.

My life blew up not long after that, and I eventually decided I needed to return to Pirates Prospects to get it where it needed to be before I venture out and one day leave this site to other writers.

At the moment, I kind of run a small record store, but that’s mostly to pay for the records I buy each year, which is a lot of records.

Fuquay Vinyl, meanwhile, is one of the big bad organizations in my “Time Travelers vs Vampires” series. That series is planned as ten novels in a multiverse following a group of time travelers who are trying to go back in time and re-write the World’s Biblical texts. My intention is to have the first book of that series released in 2024.

The book series will dive heavily into the lives of artists, with the project originally stemming from my love of 90’s Grunge artists. The main characters draw a lot of inspiration from Layne Staley, Chris Cornell, Kurt Cobain, and Eddie Vedder.

That said, the artist list I’m using for inspirations is vast, covering decades of music. Every week I create a playlist, and typically off of the vibe of that playlist, I will write something for the book series.

This week, I’m not doing any Time Traveler writing, as I’ll be busy with the site and finishing the Prospect Guide. As such, it’s a perfect week for some of my favorite 90s artists.

The Time Travelers vs Vampires project isn’t meant for Pirates fans, but right now this section is one of the few areas where I can talk about it like it’s real, and not just a collection of random writings that I’ve yet to string together into a story.

Eventually, I might use this space to preview some of my writing for that project, which will be massively different than any sports writing you’ve seen from me.

It is horror themed, so if you were around this site back in the day reading about the 2009-10 Pirates, the books might be up your alley.

WEEKLY PIRATES QUIZ

When in doubt, just start guessing former Pirates relievers. Post your score in the comments below!

HELP

Have any issues with the site or your account? Check out our Help page.