Pittsburgh Pirates: Ben Cherington’s First Year As General Manager

OAKLAND, CA - MAY 11: General Manager Ben Cherington of the Boston Red Sox stands on the field prior to the game against the Oakland Athletics at O.co Coliseum on May 11, 2015 in Oakland, California. The Red Sox defeated the Athletics 5-4. (Photo by Michael Zagaris/Oakland Athletics/Getty Images)
OAKLAND, CA - MAY 11: General Manager Ben Cherington of the Boston Red Sox stands on the field prior to the game against the Oakland Athletics at O.co Coliseum on May 11, 2015 in Oakland, California. The Red Sox defeated the Athletics 5-4. (Photo by Michael Zagaris/Oakland Athletics/Getty Images) /

It’s been almost a full year since the Pittsburgh Pirates hired Ben Cherington as general manager. How did he fare in his first calendar year on the job?

Ben Cherington has been the general manager of the Pittsburgh Pirates for almost a full calendar year. Cherington was officially named the general manager of the Pirates on November 18th, 2019.

Cherington’s first year as the general manager of the Pittsburgh Priates was far from a normal year. Yet, despite the adversity he’s experienced, he’s done a fair job with the new position. Let’s take a look at his first calendar year as general manager of the Pittsburgh Pirates.

When Cherington was hired, the Pittsburgh Pirates were not in the greatest of shape. They were coming off a 63-93 season. Before being let go himself, former GM Neal Huntington had fired 10-year manager Clint Hurdle before the last game of the 2019 season and longtime pitching coach Ray Searage just days later. Although Huntington left the club in better shape than when he arrived, there were still many problems Cherington had to face.

One of which was the direction of the club. After the Bucs made it to three-straight playoff appearances from 2013 to 2015, they would play below-.500 ball in three of the next four seasons. However, the team never fully committed to either a rebuild, or full on competition.

Despite being in a constant race for the National League Central title in those three years, they never made any moves, whether that be in free agency or in the trade market, that gave them that over-the-top edge. After the 2017 season, the Pittsburgh Pirates traded Andrew McCutchen and Gerrit Cole. Although the return for Cole was middling, overall, the Pirates looked like they were going to accept a rebuild.

But this was short lived. After an 11-game winning streak, the Pittsburgh Pirates finally made a big splash, trading three top prospects, that being Austin Meadows, Tyler Glasnow and Shane Baz to the Tampa Bay Rays for Chris Archer. The main issue wasn’t that the Pirates overpaid for Archer, although that did set them back a handful of years, but decided to go all in after trading Cole and Cutch and banking on a hot streak rather than talent like they had in ‘13-’15.

Still, between 2016 and 2018, they only won between 70-80 games. This essentially put them in a limbo-state of being not good enough to really compete and not bad enough to get a high draft pick.

Another issue that Cherington faced when taking over the club was development, especially of pitchers. Cole and Charlie Morton had finished 2nd and 3rd in Cy Young voting in 2019, and the only piece they had to show for the two trades was just Joe Musgrove. Tyler Glasnow, although unhealthy for most of 2019, likely would have also been a Cy Young finalist if he stayed healthy.

When Cherington was hired, the Pirate farm system was ranked at a solid 9th place by FanGraphs. They also were given four  top 100 prospects. These prospects were pitcher Mitch Keller, infielders Ke’Bryan Hayes and Oneil Cruz, and outfielder Travis Swaggerty.

So far, the biggest thing that Cherington has to be commended for is essentially laying out a plan for the Pittsburgh Pirates. He is wanting to take the franchise down a rebuilding path, which seems like the right move. His first big moves as GM was trading Starling Marte, and hiring Derek Shelton as manager and Oscar Marin as pitching coach.

So far, the Marte trade has looked like a massive success. One of the main criticisms many had of the old regime is that when they did trade players like Cole and Cutch, they went for quantity over quality, and pieces who might not have been exactly fantastic, but MLB ready. This time around, the main focus is talent.

Liover Peguero, the headliner of the deal, is an extremely athletic shortstop who’s seen as an above average fielder with a 60-future hit tool. Brennan Malone is a first-round pick from 2019 and has four pitches that are considered average or better, and good command.

Another move that looks like a huge success is the 2020 draft. Cherington selected Nick Gonzales with the 7th overall selection in the draft. He already ranks as a top 100 prospect by FanGraphs and MLB Pipeline. Another first-round pick in Carmen Mlodzinski is considered their 13th best prospect by FanGraphs. Four of their six picks from 2020’s draft rank within the organization’s top 30 prospects.

Player development is very important for a team like the Pittsburgh Pirates, and Cherington has made many moves to help improve that. So far this off season, he has moved Larry Broadway out of the position of farm director, hiring John Baker to take his place. He has also made a handful of other moves to scouting, development and coordination. Cherington has stated that these are far from the last moves he’s making pertaining to the development of their prospects.

One thing that he did do that many weren’t a fan of is keeping pretty silent around the trade deadline this year. Although he traded Jarrod Dyson for international bonus money, he did not move anyone else.

Now sure, he wasn’t in a huge rush to move guys like Joe Musgrove and Adam Frazier given their affordable team control, but not moving Derek Holland was something that he should have done. Even if it was for as little as some cash in return.

However, the criticism that he stayed put for the deadline is a a small blip and I think Cherington has put this team in a good position. Marin has looked like a fantastic hire so far. Although we are looking at a small sample size, Musgrove, Chris Stratton and especially Steven Brault took steps forward in 2020.

Richard Rodriguez had a nice bounceback season as well. Nik Turley and Sam Howard also flashed some potential. With a new focus on using your strengths rather than the pitch to contact method the old regime to focus too much on, it seems the new regime is really putting that focus on pitching development front and center.

After Cherington’s Marte trade and the draft, the Pittbsurgh Pirates now own a top-5 farm system. FanGraphs ranks the team’s farm at number four with six top 100 prospects. Those being the aforementioned Hayes, Cruz and Swaggerty, joined by Tahnaj Thomas, Gonzales and Peguero.

Cherington seems to have his eyes set on getting this team back into contention around 2023, but given that a handful of their prospects like Swaggerty, Thomas, Cruz and Cody Bolton all are projected to be in the majors by 2022 or earlier and the high possibility of a form expanded playoffs, they could be back in contention by ‘22.

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Overall since taking over as the new general manager for the Pittsburgh Pirates almost a year ago, Cherington looks like he’s got a plan and is doing a lot to put it into motion. However, he’s far from done. Not only has he said he is going to continue to change the Pirates’ development, but also is looking to extend some of their younger players, something he got started on doing last off season before the shutdown in March. I think the Pirates are in a much better position now than they were in a year ago thanks to many of the moves Cherington has made.