Under Ben Cherington, Pirates Return To Extreme Risk-Reward Roadmap

Image credit: (Photo by Mary DeCicco/Getty Images)

Pirates general manager Ben Cherington and his baseball operations team are playing the long game. In fact, they are playing the longest game that’s been attempted in some time in Pittsburgh.

The Pirates last undertook a rebuilding effort with a distant time horizon a decade ago, when Jameson Taillon and Gerrit Cole were selected with top two overall picks in the 2010 and 2011 drafts.

Taillon and Cole headlined an historic expenditure of draft capital on pitchers. During spring training in the early 2010s, surrounded by the orange groves and citrus farms of Bradenton, Fla., the Pirates’ backfields were growing a seemingly endless crop of projectable, 6-foot-4 or taller pitchers. In three drafts from 2009 to 2011, the Pirates allocated 22 of their first 30 picks to pitchers, with the majority from the high school ranks. It was a rare and extreme long-view, risk-reward approach.

Some of those early first-round draft picks under former GM Neal Huntington, including Cole and third baseman Pedro Alvarez, helped the club end a 20-year playoff drought in 2013 and reach the postseason three straight years.

The Pirates also benefited from buying into pitch-framing and wide-scale defensive shifting before many clubs, and also enjoyed Andrew McCutchen at his MVP peak. But the Pirates’ long-term plan to grow a sustainable crop of power arms didn’t work out like the club had hoped. A retooling effort in 2016 designed to produce a quick turnaround failed. By the end of the 2019 season, Huntington, manager Clint Hurdle and club president Frank Coonelly were gone.


In their second full year of the Cherington era, the Pirates are rebuilding as aggressively as they have since the early 2010s, again pushing return-to-contention ETAs further out into the future, and accepting greater risk for prospects of greater upside.

Since the Pirates began dismantling by sending Starling Marte to the Diamondbacks in January 2019, they have flipped their top major league players in trades centered around teenagers. Since the start of 2020, a total of 22 teenagers have been traded, according to data shared by Baseball-Reference.com and analyzed by Baseball America. The Pirates acquired five of those players, the most of any team.

For Marte, the Pirates acquired a pair of then 19-year-olds in shortstop Liover Peguero, who received glowing reviews at instructional league in 2020, and righthander Brennan Malone, Arizona’s first-round pick in 2019.

In this winter’s trade of all-star first baseman Josh Bell to the Nationals, the headliner in the trade return was 19-year-old righthander Eddy Yean. In the Pirates’ most recent deal that sent righthander Joe Musgrove to the Padres, the top prospect in the return was 19-year-old center fielder Hudson Head.

“We tried to identify some players who we think have some of the raw athletic ingredients or skills to reach a high level of performance, and in doing so, in most cases, you are going to have to accept some risk,” Cherington said. “Often that risk is represented in how young they are and how far away they are . . . Over time, the portfolio will balance out some. It’s not all going to be teenagers.”

Since the start of 2015, there have been 122 teenagers traded between clubs. While most will never reach the majors, some of those prospects included Fernando Tatis Jr., Yordan Alvarez, Gleyber Torres, Jesus Luzardo, Jarred Kelenic and, in Pittsburgh, Oneil Cruz.


A number of those players have contributed to some of the most lopsided trades in recent memory. Since the start of 2015, three teams aside from the Pirates have acquired 10 teenagers in trades: the Rays, Brewers and Padres. All three teams reached the playoffs last year.

The Pirates also hold the No. 1 overall pick in 2021, their first time with the top selection since drafting Cole out of UCLA in 2011. They may very well contend for another top pick in 2022. Recent major league history suggests bottoming out—intentionally or not—is a viable, if not optimal, rebuilding path. Not only does the team choosing first hold the top pick in each round, but it also has at its disposal the largest bonus pool to sign amateur talent.

The Cubs and the Astros collected premium pick after premium pick in the early 2010s, and that approach helped those clubs win World Series titles.

The Royals used a collection of early draft picks and prospects acquired in trades to build one of the best farm systems of the century and ultimately deliver the 2015 World Series title.

The Giants’ three World Series titles teams were anchored by top 10 overall draft picks Buster Posey, Madison Bumgarner and Tim Lincecum.

“There was no particular team blueprint that we felt was perfectly replicable,” Cherington said. “Certainly you look at what everyone has done and try and learn from that, but every situation is going to be different, because every situation is starting with a different group of players, a different circumstance, different kinds of challenges and strengths. We need to work within that, something that’s custom and specific to the Pirates.”

Given the Pirates’ bottom-tier payrolls under owner Bob Nutting, the wanting major league roster, and the good-but-not great farm system Cherington inherited, the Pirates arguably needed as deep a rebuild as any of those aforementioned success stories.

Of course, while accumulating draft capital and promising prospects is one thing, executing on development is the other key.

Where the Pirates’ early 2010s plan faltered was arguably in the development stage. Cole and Tyler Glasnow have become more dominant after leaving Pittsburgh. Taillon was traded to the Yankees this winter after showing promise but also spending much of his time on the injured list. Outfielder Austin Meadows, a heralded top 10 pick, stumbled with the Pirates but blossomed into an all-star after being traded to the Rays.

A primary focus of Cherington’s has been revamping the Pirates’ player development processes, including embracing modern training techniques, theory and technology. An improved developmental system is particularly critical for the Pirates given the younger prospects they have acquired in the last year.

“I think it’s the mindset of practice,” Cherington said. “When we think about practice, whatever type of practice it is . . . the only thing that matters is that practice has a benefit and there’s reasons to believe it has a benefit. Doing things because they’ve always been done isn’t a good enough reason. Every team in baseball is thinking about development differently.”

Another element working in favor of Cherington and his staff is ownership’s demonstrated willingness to be patient. Huntington and his staff were in charge for 12 years. While they had successes like returning the team to the playoffs, they also tallied eight losing seasons and never advanced beyond the National League Division Series.

“I don’t spend a minute thinking about how long we have,” Cherington said. “But I’ve definitely thought about (continuity) in terms of getting to know Bob (Nutting) and (team president) Travis Williams. We share a vision on how we need to go about this . . . We understand some of the things we need to make it happen.”

Pirates fans have not witnessed a playoff series victory since the 1979 World Series and they are going to have to continue to be patient. But perhaps Cherington and his team have a vision that will be worth the wait. n

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