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.


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.


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.


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.


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.

That could look different this time next year.


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Tim started Pirates Prospects in 2009 from his home in Virginia, which was 40 minutes from where Pedro Alvarez made his pro debut in Lynchburg. That year, the Lynchburg Hillcats won the Carolina League championship, and Pirates Prospects was born from Tim's reporting along the way. The site has grown over the years to include many more writers, and Tim has gone on to become a credentialed MLB reporter, producing Pirates Prospects each year, and will publish his 11th Prospect Guide this offseason. He has also served as the Pittsburgh Pirates correspondent for Baseball America since 2019. Behind the scenes, Tim is an avid music lover, and most of the money he gets paid to run this site goes to vinyl records.

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Harold Blumenfeld


Have the Pirates changed ownership? Do they have competent front office and field manager? Has their payroll risen above the embarrassment level? Despite all of their recent high draft picks, are there any budding stars on horizon? Have they stopped their tendency to fill their roster with other team’s failed prospects and mediocre veterans? Is their record trending in a positive direction? Will they trade off more of their best assets this month for more spare parts from real professional baseball organizations? So, no I just see a continuation of the same. Exhibit A….Marisnick and Yoshi are in Pittsburgh and Swaggerty and Bae are in Indy wasting yet another season.


Thanks for this positivity article. It’s really really easy to find negatives when it looks negative. It’s really really hard to find positives when it looks negative.

I have no clue if the Pirates are on the right path or not, but I will continue to be an optimist. I’m a big fan of creating as much of a positive attitude in athletes as possible. It worked with our NCAA athlete kids; emphasizing a positive attitude and strong work ethic with a little bit of a chip on your shoulder. Then, even if there is failure, you come away with a positive experience knowing you tried your best and enjoyed the ride.

If the Pirates fail, I will have enjoyed the ride because I was an optimist. Yeah it’s weird but works for me.

Last edited 6 months ago by mehutch

I agree with you Tim in that I really think BC is building something sustainable for the long term rather than just trying to catch a dash of good luck as a few good prospects emerge at the same time. We should be having waves of talent hitting each of the next several year with likely a good amount of impact talent in each wave


Good point about the waves of talent. Right now the Pirates have excellent pitching talent at MLB, AAA, and AA. Then down the road we have the likes of Chandler, Solometo, and Jones. In the draft, do we take a flyer on the best HS pitcher in 2022, Dylan Lesko? He is out until mid-2023 due to TJ surgery and rehab. Most drafted pitchers lose the whole MiLB season in the year of their draft, so all we would be missing is 3 – 6 months in 2023.


This GM has done an excellent job of placing this franchise in the position to take the next step forward. Like a previous writer, I think the decisions that will be made over the next 2 or 3 weeks will define whether we are doing something positive or not.

We have to unload the veteran players who have already been replaced in the lineup. The injuries of earlier in the year forced some young players to get to MLB quicker than originally planned, but those youngsters have proven themselves to be quite capable of playing well at the MLB level. Therefore, going back to AA or AAA for “more seasoning” will not serve any positive purpose.

We started 2022 with leaders like Reynolds, Hayes, and R Perez and we now have seen players like Suwinski and Cruz come up and take leadership roles as well. In the past week we have seen Jason Delay come up from AAA and become a solid receiver and leader for this team, and there are others at AAA who could also be in MLB shortly.

Our Rotation struggled early, but improvements by Q, Bru and Keller, and adding Contreras have this group seeing more positive results. Our bullpen is the strength of the team with Bednar leading the way, and newcomers Crowe and now De Los Santos strengthening the youth and depth of this group. And, I cannot remember a time when we had the numbers of young and very talented SP’s and RP’s at the upper two levels of the minors.

Give them wings!


I’m going to pass on this question today. I might have more of an opinion after July 17 draft and Aug 2 deadline.


Long, slow, tanking rebuilds are not only disastrous for the game of baseball, they have a way of disassociating us from the reality of competition.

Results are ignored, expectations obliterated, and bars lowered for the few remaining diehard fans who stick through them.

Are the Pirates heading in a positive direction?

Of course they are!

It would be practically impossible not to after intentionally dismantling the organization.

If the question changes to “Are the Pirates trending better than their competition?”, the answer gets exceptionally more complicated.

The Huntington rebuild succeeded by exploiting undervalued assets, and the organization’s success stalled when the league got smarter and opportunities dried up.

The biggest criticism I have of Cherington is that he doesn’t even appear to be trying.

If you follow baseball broadly across the league, it becomes clear that this iteration of Pirate Hope isn’t based on anything anyone else isn’t already doing. This version is based on doing them better than orgs who are ahead of them in time and resources.

As much as I like John Baker’s attitude, the most concerning thing about the organization right now is not the big league record but lack of results at what they MUST do exceptionally better.

Players are still leaving and getting better. Players are still failing to reach their upside. There’s no explicit improvement in number of prospects getting notably better.

The modern game is all about roster churn. Neither the A’s, Rays, or Brewers succeed by taking on these long, slow rebuilds that bank a war chest of “core” prospects that then get ridden into the sunset.

The Brewers represent everything I wish the Pirates chose to emulate. Instead, we’re left hoping the mid-teens playcard, but better, is worth all this pain.

Last edited 6 months ago by NMR

This sounds like exceptionally wishful thinking.


^ This. Spot on


I think they are headed in the right direction for sure. The brief youth movement we saw the last month or so was a great start. Unfortunately, the IR guys came back and set back the movement. Now we have to struggle again to watch has/neverbeens fail until they can be dumped. Hopefully after the trade deadline most of the deadweight is gone and they can start auditioning the kids again.


Yes, in my opinion, the Bucs are heading in the right direction. Many of the acquisitions made over the last 4-5 years (Damn it’s hard to believe it has been 5 years this month that they acquired Cruz) are just getting old enough and experienced enough to start hitting the Show. Losing the 2020 season probably kept this from starting last season. With the promotions arriving and several more soon to follow by early to mid next season, I am looking for the Bucs to add a couple of higher quality FAs than they have been signing and look for a trade or two bringing in a couple quality players to help fill the holes that they will have, namely pitching and a bat. They should be in position to be competing with the league by this time next year. It has been a fun ride to watch these kids grow and the acquisitions being made so far. Looking forward to this offseason to see where it goes.


What really surprises me is that a lot of teams, like the Reds, Angels, Tigers, etc, seemed to still be based on an old-school approach to baseball, where the writing is on the wall based on what the A’s did over 10 years ago with Moneyball. Like you said, it really does take a complete organizational change to put in that kind of institution; and like Danatur108 said in a previous comment, a lot of patience, since it is really, really hard to produce a consistently winning team.


weed cures most problems, glad you got to a good spot Tim.

As frustrating as it is that the current team isn’t winning more, a quick look at LA Angels record (only 1 win better than bucs), & realizing they have 2 of the best players in the game & an unlimited payroll, is an reminder that it’s really hard to be a winning team in the MLB.


The Angels gave Albert Pujols the richest contract in baseball, and for most of that time he was paired with one of the two best young players in the game, and for that ten year commitment, they got exactly ONE post season appearance, where they got swept 3-0! Didn’t win one post season game. Just throwing money at it is not the answer.


No, you need to spend, but wisely – at least the small market teams. That 10-year pact was an albatross almost from the start. The Pirates will need to add payroll to supplement this team in order to contend for the postseason. I am not saying Pujols money, but a $100+M payroll nonetheless.


I’m glad you found ways to take care of yourself because in the long run that’s what really matters. I hope you’re right about the direction the Pirates are headed. Some positive changes have already occurred. Let’s hope that trend continues.

As always the problem has been and will continue to be the willingness of ownership to care enough to share some of the profits with the team and fans. We’ll see. Keep thinking good thoughts.


Who knows, maybe mid-year 2023 we will have a much clearer picture…or not…


Gotta get a RH hitting 1B with power, bullpen depth and a solid No. 2 starter for this to happen, Tim, IMHO


Ivan Melendez?


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