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Part 2: Jonathan Mayo continues to evaluate Pirates farm system turnaround

The Pirates have improved from a middle-of-the-road farm system to one of the best in baseball over the past two years

Mason Martin fields a groundball
Pittsburgh Pirates

An MLB farm system is just like any other land of crops, the more nutrients and fertilizing the land receives, the greater the product. The more players Ben Cherington continues to add to the Pittsburgh Pirates organization, the greater chance of a better future for October nights at PNC Park.

The system has been rebuilt from a middle-of-the-pack disappointment to a legitimate top-three ranking since organizational turnover shifted to Cherington in November 2019.

MLB Pipeline’s Jonathan Mayo is one of many farm system analysts to take note of the Pirates’ recent transactions, adding four of the draft’s top prospects with their first four picks to an already talented group of Minor Leaguers. The most noticeable players are all developing between A-ball and AA, displaying the Bucs’ focus on acquiring prospects with high-upside and trusting their pro scouting to identify players and staff to develop them internally. May said:

“I think some of what this group in Pittsburgh has done is identifying those lower-level guys who haven’t played in full-season ball yet but have interesting attributes. They’ve done a very good job of scouting those and bringing some of those guys into the system.”

The plan Cherington has put in place requires patience and trust in a better future, something tough for fans to live with due to past failures. Mayo said the revamped front office is looking to learn from those mistakes and identify solutions no matter the timeline.

“I think what Cherington’s been able to do is look at it from a long approach. This wasn’t a flip a quick switch and get guys who are as close to big-league ready. The years Neal (Huntington) was here and they were trying to maintain winning, they would often make trades for guys who were at AAA or had touched the big leagues with years of control so they could turn it over relatively quickly. They had mixed results with that.”

Mayo said that adding potential impact players was needed, but acquiring depth pieces that could surprisingly blossom into untapped abilities is worth the gamble.

“He realized that there was a need not just for quality but quantity. What they were able to do with some of those trades in targeting guys with high upside who are a little bit further away, we’re seeing some guys who were better than expected. Roansy Contreras is way better than expected so far.”

Contreras, acquired by the Pirates in the Jameson Taillon deal, is the biggest riser in the organization despite not pitching since June 30 with a forearm injury. In nine starts spanning 46 innings, the right-handed Contreras holds a 2.35 ERA with 11 walks and 65 strikeouts for the Altoona Curve (AA).

“In terms of what he’s been able to do, his stuff is all ticked up and he’s maintained his command so he’s probably the guy who I would point to first.”

The Taillon trade, consisting of Contreras, right-handed pitcher Miguel Yajure, outfielder Canaan Smith-Njigba, and shortstop Maikol Escotto has replenished the system in one transaction, with Mayo stating that Escotto, thought of as the last piece of the deal, could be the best played acquired for Taillon, with no clear picture painted for another four years.

The first impactful move Cherington made, dishing Starling Marte during the 2019 offseason to an Arizona Diamondbacks team currently last place in all of baseball, resulted in the acquisition of shortstop Liover Peguero and right-hander Brennan Malone.

Peguero has improved his swing path and has shown flashes of greatness for the Greensboro Grasshoppers (A+), while Malone has regressed and was demoted to the Pirates FCL Pirates Gold rookie team to refine his mechanics and control. Despite Malone’s struggles, Peguero could add subsequent value after being thought of more as a lottery ticket when acquired as an 18-year-old yet to play a full season of pro ball in exchange for the only 33 games Marte played in the desert.

“Liover Peguero is going to be really really good. That trade is going to end up being a very good trade for them. He’s (Malone) a project. Think of him as just having drafted a super projectable high school right-hander who is raw…. If he ends up not being anything and Liover Peguero is your starting shortstop someday… that’s a good trade.” -Mayo

One organizational focus Cherington’s staff has prioritized is not just improving players’ individual skills but also teaching them how to win ball games in preparation for pennant races a few years down the road. Playing against strong competition at AA has helped Curve players be prepared for AAA, with the two-class levels being discussed where the greatest level of development occurs. Mayo thinks the viewpoint of the two has varied throughout the years.

“I think for years and years if you can compete and succeed in AA, you can play in the big leagues. AA was always the best prospect league. When the men were separated from the boys. That jump from A-ball to AA was often the biggest. For the longest time, AAA was that place where the AAAA guys or the veterans would be in that holding pattern. Over the last several years, having guys stop for longer at AAA from a development standpoint has become more important.”

First base prospect Mason Martin has been one of the most dominant hitters throughout the Minor Leagues, punishing baseballs onto the roller coaster just outside of Peoples Natural Gas Field. Martin has ranked in the back half of the Pirates' top prospect lists despite owning the best power in the system as a true threat to hit the ball out of the yard and drive in runs. Part of the reasoning for his lack of acknowledgment is Martin’s high strikeout rate, defense, and inability to play another position.

“I think he’s always going to be streaky, he’s always going to strikeout… Mason Martin has some bat speed. Moving to AA is a big thing. How much is that strikeout rate going to be a problem? I don’t think it’s a problem. Everyone’s striking out now. He’s drawing enough walks to offset it, but to me, what he’s doing now means he’s going to do that in the big leagues at some point soon. But he’s first-base only, he’s turned himself into a capable defender there, but he’s never going to be one of these gold glove caliber first basemen… The limited profile does limit where he goes on a prospect list for sure.” -Mayo

With Altoona beginning to play home to the Pirates' best Minor Leaguers, the notion that 2023 could be the Bucs’ year to make a dent in another pennant chase is fueled by ETA’s listed by prospect sites. Mayo said that the ETA’s should be taken with a grain of salt, especially after no Minor League season in 2020 marking the first full year of baseball for numerous individuals, pointing to 2024 as a potentially more realistic answer.

“When we put those ETA’s I try to bridge, I don’t want to be too conservative and I don’t want to be too optimistic. I feel like ‘24 is more like it. ‘23 some of those guys get there and they’re the kind of team like the Padres were a couple years ago that no one wanted to play because they were getting better and had absolutely no fear because they were young. This year is such a weird year in terms of trying to figure out what it means because of the off-year. It wouldn’t surprise me if guys (like Quinn Preister) could take a huge step forward and be in the big leagues next year. Then 2023 becomes more feasible.”

Many fans and observers of the Pirates under Huntington continuously pointed out the GM’s lack of aggression in promoting top prospects to higher levels of the Minor Leagues, stressing the need for more seasoning before advancing forward closer to the big leagues. Mayo stressed that each situation can vary across the league and how the roster construction can balance.

“Sometimes it’s the Minor League system. There’s only so many places you can put these guys. There’s four affiliates and the complex league. You have to sink or swim some of them anyway and a lot of them are swimming so that’s a good sign.”

Mayo ranks the Pirates top 30 prospects for MLB Pipeline, with updated rankings being released in mid-August after the conclusion of the trade deadline and finalization of signing draft picks. With still work to do and the process only beginning, Mayo credits Cherington for getting off to a good start with player identification and trades to turn the Pirates into a winning organization.

“You can grade out a general manager now but the end result is ‘what is this team going to look like in three years.’ Everything is pointing in the right direction. I think he has done a very good job at getting returns for players.”