Williams: Are the Pirates Headed in a Positive Direction?

The Pittsburgh Pirates are headed in a positive direction.

Some nights, it’s difficult to see that trend.

If you look at the long-term, it’s easier to see.

A year ago at this time, Oneil Cruz was injured in Double-A Altoona. Today, he’s got a .681 OPS in Pittsburgh, largely fueled by his power.

Where is he going to be next year, after getting a full year of experience in the majors?

A year ago, the Pirates hardly had any prospects in the majors. This year, they have Cruz, Roansy Contreras, and a large group of players making their MLB debuts. That group has led to the breakout performance of Jack Suwinski, along with a few other 45+ grade prospects who are trending toward being players who can fit on a contender.

You can already anticipate the potential 2023 arrivals of top prospects like Mike Burrows, Quinn Priester, Liover Peguero, and maybe Henry Davis. Aside from them, the Pirates are set up to have another Suwinski type breakout next year with all of the 40-45+ grade prospects in the upper levels.

It’s easy to see how the talent is stacking up over the last year. The draft gave a huge boost to the lowest levels, while the trades boosted that 40-45 grade depth in the upper levels.

I would expect a similar outcome this year, meaning that next year this system will still look stocked, even after more prospects arrive.

The thing about heading in a positive direction is that it’s difficult to find hard evidence of that fact. It’s impossible to really know what direction — positive or negative — any team is trending in the long-term. We mostly only care about now.

The Pirates are a losing team right now.

They want to be a winning team.

Every move they make is to advance their organization in that direction, piece by piece.

So, how can we know if they’re heading in a positive direction for sure?

The simple answer is that we can’t.

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I’ve been asking a lot of my friends what Positivity means.

The most common response centers around positivity being a mindset. Having a positive attitude, even in the face of negative events. This mindset usually expanded to a strategy in how to use that mindset — actively convincing yourself that things are better than they seem.

I think that Positivity is a lifestyle. I think what most people perceive as positivity is actually a symptom of the lifestyle.

Positivity is a routine that encompasses your entire life, with a goal of moving everything forward in a positive direction over the long-term, and trust in yourself to achieve this progression. In the short-term, there will be speed bumps and setbacks, but the self-trust gets you through the unknown.

If you’ve ever met a truly Positive person, they don’t greet problems with false positivity. They analyze the entire situation, recognize the overall negative, extract the positive lessons to take forward — and then they move forward.

It’s the Negative person who greets problems with false positivity and a “Good Vibes Only” attitude. The Negative person projects out a positive vibe, but makes no effort to address a negative situation. As a result, the negative repeats, as it is never recognized as a negative. The positive lessons within the negative go unnoticed — or perhaps noticed but with the belief that those positives can’t exist without the negative approach.

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You can’t just become the Rays.

It takes more than an attitude.

It takes planning. It takes a strategic mindset that permeates through your entire organization. It takes an ability to adapt to all of the variability that will hit any plan — especially one designed for Major League Baseball.

Small market teams can fake a positive organization with temporary surges and windows of contention.

We know from the Oakland Athletics and the Tampa Bay Rays that small market teams can contend in the long-term.

We know from Neal Huntington that the Pittsburgh Pirates can contend in the short-term.

I have no doubt that Ben Cherington can get the Pirates back to the playoffs for a similar window. From my perspective, Cherington is trying to build something bigger — a small market team that can contend on a long-term basis.

The Rays/A’s of the NL.

Neal Huntington built the Pirates to the point where they can contend. Turning the organization into the NL version of the Rays/A’s would be the logical next step for Cherington.

That’s probably the only way the Pirates contend long-term in a division with big budget teams like the Cubs and Cardinals, along with the Brewers — who are arguably already the Rays/A’s of the NL.

It would have been easy for someone to come into this organization and attempt a quick turnaround to reach the playoffs.

That would have resulted in another quick window.

What I’ve seen from Cherington is building the foundation of this organization. He’s building a larger organization, which should be capable of maintaining winning long-term through talent acquisition, strategy adaptation to a changing league, and process management for the plan in place.

In 2022, it’s no longer on the General Manager alone for all of this. The best organizations have multiple General Managers running their departments.

The Rays are a model organization, not just a team, for this reason.

The Pirates can’t win as a team like the Rays until they build an organization like the Rays.

Between Cherington’s approach to expand the organization, and farm director John Baker’s focus on mindset and building up the self-esteem of players, I see a comprehensive plan that will send the Pirates in a positive direction.

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Maybe I’m aware of this because I went through a similar process recently.

In 2015, I switched this site to a subscription model. We had over 5,000 subscribers in the first year. For three years, I used that revenue to try and run a small media outlet, while also trying to be a full-time reporter.

By 2018, I had added a house with way too many problems to fix, and was in the start of a serious relationship that would eventually have way too many problems to fix. I was also starting to realize that I couldn’t be both a reporter and the manager of a media outlet.

I had a very positive site, but my overall life was Negative.

I ran into the issue of Volume, where I didn’t have enough time to do all the things I needed to or wanted to do in my life. I needed better time management and better executive decisions to figure out what I wanted to do in the time I had, while living a life outside of work that would be healthy and positive.

So, for three years I worked on building up the new plan for the site in my mind, while also going through therapy and removing negative influences from my life.

This year, I’ve been implementing the new plan, with a better foundation to the site, a better mindset on how to manage things when everything spirals, and a better routine to always be advancing the plan in a positive direction, regardless of if the short-term feels negative.

The therapy I went through to remove the constant self-doubt I had was probably the biggest improvement. I didn’t have a good support system growing up, and have always had self-doubt. If anyone is looking for the cure, roughly an ounce of marijuana will do the trick.

Perhaps that’s why I was on board with this plan when John Baker was added — not because of weed, but because he was bringing psychology and a better mental health approach to the player development side.

When I left the reporting side in 2018, most of the calls I got from scouts were asking more about the mindset and personality of the players, rather than what they could do on the field.

This is where the game was trending before Cherington took over.

And Cherington’s old organization, the Toronto Blue Jays, were one of the most aggressive in this approach of adding people, not players.

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John Baker is just part of a trend of this growing organization.

He’s got ideas on how to make the organization better from his department, and the freedom to implement those ideas.

Cherington has been pretty hands off each department, instead running the overall organization and trusting the people in place. The departments have grown, with smaller departments growing within each system.

The biggest negative I see with this organization is that we’re in year three under Cherington and the Pirates are one of the worst teams at the MLB level.

However, I see a lot of positive trends at the big league level, along with a lot of positive growth in the minors. A lot of that is natural. It’s not forced. It’s just the plan slowly playing out.

Eventually, I think those positive trends will lead to a contender in Pittsburgh. And I think the wait will allow for that contender to stick around for longer than three years.

I don’t think this organization could have been built to a potential Rays/A’s level without such a deliberate approach.

Right now, I think we’re in the point in time where it’s hard to see positivity from this approach, especially when the negative is so obvious at the highest level.

The most difficult thing when looking for positivity from a previously Negative approach is that you only have proof of the negative.

Ben Cherington ultimately has the daunting challenge of turning the Pittsburgh Pirates from a Negative organization to a Positive one.

I think that has already taken place.

I just don’t think we’ve seen the positive returns at the big league level yet.