Williams: This All Certainly Feels Familiar, in a New Kind of Way

I’ve been here before.

It’s August 1st and it feels like there’s nothing to do for the rest of the year.

The Pirates have drafted and signed the players they will draft and sign this year.

They have traded MLB players for prospects at the deadline.

The final two months of the season will feature this MLB team and this MiLB system.

The MLB team? A losing one. A team that will likely finish with one of the worst five records. Yet, still a team that manages to provide a surprising amount of hope for the future.

But we’re not here to talk about the current MLB team.

This is a space to discuss the minor league system.

Welcome to Pirates Prospects.


I’ve been here before.

The Pirates are a losing team, and yet there is hope rising from the farm system ranks.

They just completed a draft that brought in a haul of talent. The Pirates had the number one overall pick, and took the fourth best prospect in the draft, per Baseball America rankings. With the savings from that, and other day two picks, they landed three more players in the top 32, plus a day three pick ranked inside the top 100.

Over the last eight months, the Pirates have also traded away Josh Bell, Joe Musgrove, Jameson Taillon, Adam Frazier, Richard Rodriguez, and others, getting over 20 prospects in trade returns since the start of this trading cycle. Several of the prospects added in the early moves have already taken big steps forward this year.

Pirates’ General Manager Ben Cherington has massively boosted the farm system in the last year, taking the organization from middle-of-the-pack range to one of the best systems in the league.

The MLB team is still one of the worst in the league, but the first two drafts under Cherington have been well-regarded, and there’s a trend starting to develop on the trade front where this organization can spot players who have taken a step forward, before that step is considered in their national prospect rankings.

These are signs that you want to see from a front office. These are trends you want to see from a losing MLB team’s farm system.

They all lead to one thing: Hope.

Hope that things will turn around in the majors one day soon.


I’ve been here before.

I’ve covered a losing Pirates team with a top farm system and plenty of hope for the future.

For that matter, I’ve covered a winning Pirates team with a top farm system and plenty of hope for the future.

That losing team became a winning team, though not entirely because of the farm system.

That winning team became a losing team once they started banking entirely on the farm system.

From a larger scale, this organization overhauled their scouting department and process under Neal Huntington, and started getting better prospects than ever before in the system.

Unfortunately, their development system needed work. That was feared to be a problem during their 2013-15 winning seasons, when they were winning largely with help from shrewd MLB additions like A.J. Burnett, Russell Martin, and Francisco Liriano. Sure, they had help from the farm system with guys like Gerrit Cole and Starling Marte playing big roles, along with guys like Josh Harrison and Jordy Mercer filling starting spots with league-average production for a few years.

The Pirates had the best system in the league in 2014, per Baseball America. Here was that top ten, and how it turned out:

1. Gregory Polanco – Had a few 2-2.5 fWAR years, but has been replacement level under his extension since 2018.
2. Jameson Taillon – Posted a 3.9 WAR in 2018, then underwent his second Tommy John in 2019. Was traded to the Yankees in January for Miguel Yajure, Roansy Contreras, Canaan Smith-Njigba, and Maikol Escotto
3. Tyler Glasnow – Traded for Chris Archer at the 2018 trade deadline.
4. Austin Meadows – Traded for Chris Archer at the 2018 trade deadline.
5. Nick Kingham – Replacement-level for the Pirates over two seasons, now pitching in Korea.
6. Alen Hanson – Barely got time in Pittsburgh in 2016-17. Career highlight was an 0.5 WAR season in 2018 on the Giants’ bench.
7. Josh Bell – Spent the first two years being a sub-1.0 WAR player, then posted a 2.4 WAR in 2019. Was traded for Wil Crowe and Eddy Yean last Christmas eve.
8. Reese McGuire – Traded in 2016 to the Blue Jays, packaged with Francisco Liriano for salary relief.
9. Harold Ramirez – Traded in 2016 to the Blue Jays, packaged with Francisco Liriano for salary relief.
10. Luis Heredia – Released after topping out in Double-A in 2017.

This group hasn’t led to horrible results. The expectations obviously weren’t met for various reasons. What’s worse is that after 2015, the Pirates didn’t really have a clear plan for these guys, or other guys who joined them at the top of the system.

Reese McGuire and Harold Ramirez had both seen a decline by the time they were traded with Francisco Liriano, though you never want to see a small market team trading prospects for money. You want to see the opposite, such as the recent Adam Frazier trade, where the organization is spending to make sure they get the best prospects possible.

Guys like Gregory Polanco, Jameson Taillon, and Josh Bell showed flashes of their potential. Ben Cherington was able to salvage value from Bell and especially Taillon, with Roansy Contreras looking like an easy top ten prospect in the system heading into 2022.

Austin Meadows and Tyler Glasnow were traded with 2017 first rounder Shane Baz for Chris Archer in a deal that could haunt this organization for years. It was the move that ultimately ended Neal Huntington’s tenure as the General Manager, with Glasnow and Meadows immediately having success in Tampa, and Archer declining rapidly after the deal.

The damning thing is that the Pirates had the top farm system in 2014, and the only player from this list who contributed to any contending Pirates teams was Polanco in his debut years in 2014-15, with his highlight then being a 2.2 WAR in 2015. The later positive results from guys like Taillon and Bell led to lowered draft positions in years when the Pirates were, at best, an 82 win team.

Ben Cherington appears to have a plan to rebuild this organization.

That plan isn’t much different from the plan Neal Huntington had. Spend big in the draft, trying to get as many talented players as possible with over-slot deals. Trade players who won’t help your big league team win for prospects who might one day help your big league team win. Add low-cost talent through any means necessary, trying to find a sleeper to boost your MLB team in addition to those future prospects.

Huntington overhauled the scouting department during his time with the organization, with a massive change in the amateur scouting department between the 2009 and 2011 drafts. The player development system saw a lot of changes from where it was left with Dave Littlefield, becoming a more cohesive unit that worked together. However, the development of prospects was lacking, with most prospects in the system falling short of even 50th percentile projections.

Cherington’s plan can work. He will just need to improve the development system in the same way Huntington improved the scouting system.


I’ve been here before.

This is my 13th season covering the Pittsburgh Pirates and their farm system.

I’ve been called many names during that time.



He Who Remains.

An asshole.

But, it’s not as simple as a name.

The prospect landscape is a landscape of failure. The odds of making it to the majors for any prospect is ridiculously low. The odds of a top prospect becoming a top major league player are also low.

You could look at the struggles from that 2014 top ten list above and chalk it all up to “Prospects will break your heart.” You could probably find worse outcomes from a top ten list that year. You could go lower in the system and find players who worked out better than some of those top ten guys.

My job here has always been to sift through tons and tons of data, live reports, and project out the future physical and mental development of every player in the system.

It’s a job that leads to a ton of failure. No prospect prognosticator avoids it.

That top ten list from 2014 was from Baseball America. It wouldn’t have mattered much if I picked any other outlet, including this one. We all had the same top ten, with a few players flipped among the ranks. We all saw the same potential in those players, and we all saw the same loaded system.

My job here isn’t to tell you which prospects will become MLB players.

I mean, technically, that’s part of my job. It’s the biggest draw to a prospect site.

Except, I’m going to be wrong most of the time, because these are human beings, and it’s very difficult projecting out human behaviors and accomplishments.

No, my job is to tell you how.

How will these players reach the majors? How will the Pirates eventually win with these prospects?

Those questions are answered by assembling a massive puzzle. Each prospect is a piece of that puzzle, and their development plan is what shapes them.

It’s my job to describe the shape of the pieces, tell you how they fit in to the overall puzzle, and ultimately tell you if the puzzle is looking like the cover of the box that you purchase any time you say that Ben Cherington has this organization on the right path.

I think he does.

Perhaps that’s just the prospect analyst in me. You’re surrounded by so much inevitable failure that your only choice is to seek out signs of hope and optimism.

It’s why I can tell you how every player could reach the majors, with different probabilities on each guy.

It’s why I could say a decade ago that Neal Huntington had the team headed in the right direction, be correct about that statement, but still be wrong about the how.

I think Ben Cherington will get the Pirates back to being contenders, and the “how” involves more of what he’s already done. It involves more drafts like this one, more scouting success stories in trades like with Roansy Contreras, and a building plan that is obvious to everyone watching.

That “how” also involves improvements in the player development system.

I’m optimistic in that regard, based on conversations with new farm director John Baker, along with conversations with players who have been in the system since Huntington was GM and have noted the changes under Cherington.

The Pirates are a losing team right now, but they’re adding talented prospects in bulk, they’re addressing the player development shortfalls from the past, and they’ve got a General Manager who has shown an ability — past and present — to find talent at a discount for the MLB team, beyond just prospects.

Fix the development system, and this team could be fun to watch over the next decade. For more than three years this time.


I’ve been here before.

I’m so glad to be back.

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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