Ben Cherington has been the General Manager of the Pittsburgh Pirates since 2019. He has failed at almost every trade he has made since being hired.

Let’s breakdown and grade some of his big trades throughout his tenure.

Starling Marte Trade

When Ben Cherington was hired as general manager back in 2019, he immediately started to trade off all of the his assets to rebuild and construct his own roster. His first trade he made as GM came on Jan 27th 2020 when he traded one of the Pirates best players in most recent memory, Starling Marte. He was traded for RHP, Brennan Malone and SS, Liover Peguero from the Arizona Diamondbacks. Since the trade, Marte has a combined 11.1 bWAR while Peguero has a  -0.3 bWAR and Malone has not even reached High-A ball due to injuries and struggles in the lower level minor leagues. Liover Peguero has shown some flashes as of late, but overall the trade has been a massive disappointment to the organization. Grade: D-

Josh Bell Trade

His next big trade was when he sent 1B, Josh Bell to the Washington Nationals in exchange for RHP, Eddy Yean and RHP, Wil Crowe. The Pirates have not had a true first baseman since this trade. The failures at that position for the franchise since this trade is what makes it even worse for fans. As of today, Wil Crowe is not even in Major League Baseball anymore and Eddy Yean has been with the organization for 5 years and has yet to make his major league debut with the team. Josh Bell has had double digit home runs every year since being traded and even though he is not a good defender, the Pittsburgh Pirates could have used his power these past 6 years. Grade: F

Joe Musgrove Trade

On January 19th 2021, Ben Cherington traded away one of his best pitchers in the Pirates starting rotation, Joe Musgrove. In return they got C Endy Rodriguez, RHP David Bednar, RHP Drake Fellows, OF Hudson Head, and LHP Omar Cruz in the three team trade that involved the San Diego Padres and The New York Mets. This trade was not as bad of the previous ones just because David Bednar has been one of the best closers in the game of baseball and Endy Rodríguez has shown promise and was once ranked the 55th best prospect according to MLB Pipeline. The big problem with this trade is only getting a closer in return for a talented top of the rotation starter. Many consider this a failure because of that reason. Grade: D+

Jameson Taillon Trade

A few days after he traded Joe Musgrove to the San Diego Padres, Ben Cherington then traded away home grown pitcher, Jameson Taillon to the New York Yankees. In return, the Pirates received RHP, Roansy Contreras, SS Maikol Escotto, LF Canaan Smith, and RHP Miguel Yajure. At first, this seemed like a good trade for Cherington. Roansy Contreras was showing a lot of promise in the minor leagues and looked to be part of the future for the Pittsburgh Pirates. However, he eventually flamed out with the organization and was DFA’d in 2024. None of the other players in this trade has had any success with the Pirates. Canaan Smith is no longer in baseball, Miguel Yajure is now pitching overseas, and Maikol Escotto is still in the farm system, but has not progressed passed Double-A. Cherington traded away 2 quality starting pitchers in the organization in the matter of days for essentially nothing in return but a closer. Grade: F

Adam Frazier Trade

Ben Cherington’s next big move was on July 26th 2021 when he traded 2B Adam Frazier to the San Diego Padres for SS Tucupita Marcano, RHP Michell Miliano, and OF Jack Suwinski. At the time of the trade, Frazier was in the prime of his career. He was slashing .324/.388/.448 with the Pirates and was one of the hottest trade pieces at the deadline. The headliner for the trade was Tucupita Marcano. He was the Padres’ #6 prospect and there were rumors that Cherington was wanting to trade for him during the offseason before the season started. He eventually got his guy, but it did not pan out well for him. Marcano had a combined -1.0 bWar in two seasons with the Pirates and was eventually banned for life from playing MLB for gambling on games. Miliano never passed Double-A with the Pirates an has not been in professional baseball since 2023. However, Jack Suwinski started off very hot with the organization. In his first two seasons with the Pirates he had 45 home runs in his first 250 games. In 2022, he slashed .202/.298/.411 with an OPS of .709 and the nest year he followed that up slashing .224/.339/.454 with and OPS of .793. The Pirates thought they might have found a hidden gem with Suwinski but unfortunately that was not the case. In 2024, he struggled mightily finishing the season slashing just .182/.264/.324 with only 9 home runs. He had bWar of -1.7 and showed no power at the plate. This year he hasn’t improved at all and has actually gotten worse. He is slashing .103/.247/.163 with only 1 home run in 30 games. Grade: D-

Clay Holmes Trade

On the same day, Ben Cherington also traded relief pitcher, Clay Holmes to the New York Yankees. The Pittsburgh Pirates got SS, Hoy Park and SS, Diego Castillo in return. I wont go into much detail about these two players because there is not much to say. Park is no longer in Major League Baseball and Castillo has been with many other teams playing in the minors since the trade. Clay Holmes was a great closer with the Yankees and had a combined 5.1 bWAR with them before signing with the New York Mets this year to become a starting pitcher. As of today, Holmes is in the Mets starting rotation where he has a 3.45 ERA and currently a 1.2 bWAR in 22 games. Grade: F

Jacob Stallings Trade

We now move to November 29th 2021, where Ben Cherington makes another trade involving Gold Glove catcher, Jacob Stallings. Stallings was traded to the Miami Marlins for RHP Zach Thompson, RHP Kyle Nicolas, and OF Connor Scott. Stallings was coming off a stellar year slashing .246/.335/.369 with 8 home runs and a 3.0 bWar while also winning a gold glove award for his impressive defense that season. The trade package itself is what really bothers most fans. Stallings was still in Arbitration with a few more years of team control. He was one of the best defensive catchers in the game at the time and Cherington did not get enough for him. Thompson was eventually DFA’d by the Pirates in 2023, Scott was released in 2024 and has bounced around with some other teams and hasn’t reached the major leagues. Kyle Nicolas has shown the most promise, but has struggled for the most part and hasn’t reached his full potential due to command issues. He is still with the organization, but only getting Nicolas back in the trade makes this another failure. Grade: F

Quinn Priester Trade

On July 29th 2024, Ben Cherington traded RHP Quinn Priester to the Boston Red Sox for 2B Nick Yorke. At the time, most fans were fine with the trade because Priester struggled most of the time while here in Pittsburgh. In 2023, Priester pitched in 10 games with the Pirates and had an ERA of 7.74 with a 1.70 whip. The following year he had a 5.04 ERA before he was traded away to Boston. Nick Yorke was the Red Sox #8 prospect and was playing well in AAA before getting traded. He was slashing .310/.408/.490 in 38 games with Worcester. As of today, Yorke has yet to see action with the big league team this season after a short stint in 2024. He has struggled in AAA this season while Priester was traded into the division to the Milwaukee Brewers and has a 10-2 record with a 3.27 ERA. Talk about adding more salt to Pirates fans wounds. Grade: D

Bryan De La Cruz Trade

The next day, Cherington traded for OF Bryan De La Cruz from the Miami Marlins in exchange for RHP, Jun-Seok Shim and 3B Garret Forrester. Shim was the Pirates #18 prospect while Forrester was their #19 prospect during that time. The problem with this trade wasn’t the players he traded away, it was trading for De La Cruz when the team needed a better bat to stay in contention for the playoffs. The Pittsburgh Pirates were 55-52 at the time of the trade and needed to add a good bat to solidify the middle of the lineup. De La Cruz was coming to the Pirates with only a .289 OBP which was not good enough keep this team afloat. He played 44 games with the Pirates after being traded and slashed .200/.220/.294 and only had 3 home runs. A lot of fans thought Cherington could have traded for a better bat that could have helped the team possibly make the playoffs. He failed to do so and at the end of the season, De La Cruz elected free agency. Grade: F

David Bednar and Bailey Falter Trade

Now we come to the most recent trade deadline. Ben Cherington made some puzzling decisions to say it lightly. He traded star closer, David Bednar to the New York Yankees and in return got back their #8 prospect, C/1B Rafael Flores, C Edgleen Perez, and LF Brian Sanchez. Cherington later admitted their were better ranked prospects on the table for a trade, but decided to go with this package because he liked the players being brought back to the Pirates. He then traded LHP Bailey Falter to the Kansas City Royals in exchange for LHP Evan Sisk and 1B Callan Moss. Falter still had multiple years of team control left and was pitching very well on the season. Before being traded Falter had a 7-5 record with a 3.73 ERA and a whip of just 1.18. Sisk is a 28 year old reliever that has only been in 5 major league games while Moss was an undrafted free agent pick up last year for the Royals. Moss was slashing .268/.370/.412 with 9 home runs before being traded. Grade: D-

All of these trades throughout the years have pushed the Pittsburgh Pirates more in the depths of baseball hell. The fans have had enough of the incompetence and lack of awareness from ownership and this general manager. They need to right the ship and start making moves to help bring back hope to the fanbase. Many fans think Ben Cherington should not be back and it is hard to blame them. There hasn’t been many positive things for this franchise as of late and it seems like that’s continuing after this past trade deadline as well. Looking back at all of these trades, its clear Ben Cherington has hurt this organization more than he has helped it.

He has failed Pirates fans.