Grading the Pirates' trade deadlines under Ben Cherington

For the first time during Ben Cherington's stint in Pittsburgh, he is looking at being a potential buyer at the MLB trade deadline. In all of his seasons as the Pirates' general manager, he has instead been tasked with selling, stripping a roster down to its parts for the opposite of a second-half surge.

As it stands right now, Cherington must instead fuel a successful stretch run, and in order to improve the team, he needs to acquire major league talent. Acquiring talent has been the goal at past deadlines, too, but Cherington has looked to infuse the system with minor leaguers instead of win now. Even though this deadline is set to be different from all his previous work, it's worth grading every trade deadline that Cherington has managed during his time in Pittsburgh to see if he's successfully executed his vision.

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Based on Ben Cherington's past trade acquisitions at the MLB trade deadline, can the Pirates successfully buy?

2020: A

There was not much of a trade deadline in 2020 for the Pirates. The only trade they made was sending outfielder Jarrod Dyson to the White Sox for international bonus pool money. This helped the Pirates sign Po-Yu Chen, who has been one of the Pirates' better pitching prospects this year on an elite Altoona pitching staff.

With the Pirates in 2020, Dyson had a batting average of .157 with five runs batted in. He also had an OPS of .375, which includes an on-base percentage of .218 and a slugging percentage of .157. He was one of the worst hitters in the league at that point, but the Pirates were able to get something out of him, which resulted in signing one of the most underrated prosepcts in the organization in Chen. Since Cherington got that pool money out of a very poor Dyson, this deadline is safely graded an A.

2021: D

The 2021 trade deadline did not turn out well for Pittsburgh despite the Bucs getting back 10 players in five trades. Only two players the Pirates acquired from that trade deadline remain in the organization, and both have not exactly been successful.

The biggest trade from that deadline involved sending Adam Frazier to the Padres in exchange for Tucupita Marcano, Jack Suwinski, and Michell Miliano. Frazier was excellent in the first half, which got him into the All-Star Game, allowing him to be maximized and dealt for this package. Marcano is no longer in the league after gambling on games, and Miliano was released from the Pirates and remains a free agent.

Suwinski is the only player in this deal that has made a signifcant impact on the team, which really has saved this deadline from being an F. He had his best year in 2023 with an OPS of .793 and a wRC+ of 112, but has struggled to find a groove at the plate in 2024. His career is far from over, but he needs to develop still. He is the best addition from this deadline, but for now, this trade doesn't represent success, either.

Another trade that involved multiple players was sending Clay Holmes to the Yankees in exchange for Hoy Park and Diego Castillo. When the Pirates traded Holmes, it looked like a fleece. He had a 4.93 earned run average and a WHIP of 1.43, which were both career highs, but Cherington somehow got two prospects out of him. Unfortunately, it did not work out as planned.

As soon as Holmes joined the Yankees, he turned his career around by becoming a dominant closer. With the Yankees, Holmes has a 2.56 earned run average with a WHIP of 1.09, striking 211 batters in three years. He's also made it to two All-Star Games in three full seasons with the Yankees. The Pirates may have gotten rid of him too early, but they thought they were getting two solid prospects in return. That was not the case, and he has since been unlocked.

Castillo was very good during 2022 spring training, but as soon as he got called up, his bat cooled off, which resulted in him being designated for assignment after the season. He had a .633 OPS with 11 home runs and 29 runs batted in during his time in Pittsburgh. Park's time with the team was very similar; he posted an OPS of .637 with five home runs and 20 runs batted in during two seasons in Pittsburgh.

Park was designated for assignment and eventually traded for a young pitcher in Inmer Lobo, who has been lights out for the Pirates' Single-A affiliate in Bradenton. He is 20 years old with a 1.50 earned run average in 30 innings pitched and has struck out 39 batters. Opponents are batting .163 against him and his WHIP sits at 0.77. This is a sneaky solid arm in the organization, which came courtesy of Park, but ... it's hard to credit Cherington's 2021 deadline for that directly.

The last player the Pirates traded in exchange for multiple pieces in return was Richard Rodriguez, who went to Atlanta in exchange for Bryse Wilson and Ricky DeVito. Rodriguez was a very good reliever for Pittsburgh, but he'd reached peak value, so Cherington took advantage. This trade would have been a big win for the Pirates ... if either pieces of the return could have been productive in Pittsburgh. Rodriguez did not even make the Braves' playoff roster and has not pitched in the majors since 2021.

DeVito pitched a season in Greensboro and struggled, becoming a minor league free agent after the campaign. Similarly, Wilson did not perform well with the Pirates, posting a 5.37 earned run average in 156 innings pitched with a WHIP of 1.37. That was not the last the Pirates saw of Wilson, as they traded him to an in-division rival (the Brewers). He has been a great arm in Milwaukee, as he has posted a 3.38 earned run average and a WHIP of 1.17.

The next three trades were all one-for-one deals, headlined by rental left-hander Tyler Anderson. If there was one thing Cherington excels at, it's finding soft-tossing southpaws to thrive in the Pirates' rotation. Anderson posted a 4.35 earned run average in 103.1 innings pitched and he had a WHIP of 1.20. In return, the Pirates got a young catcher in Carter Bins from the Mariners.

Bins has not done much in his career in the minors. He is now 25 years old and remains in Double-A. In his minor league career, he has a .215 batting average with an OPS of .723 and has hit 35 home runs. He has not been very productive, but the Pirates took a chance on him with this trade.

Another one-for-one deal involved sending Austin Davis to the Red Sox in exchange for Michael Chavis. Davis pitched 9.2 innings with the Pirates in 2021 and generated a 5.59 earned run average. The fact that the Pirates were able to get a former top-100 prospect out of Davis was incredible.

Chavis was a former top name, but did not do much with the Pirates. He hit 15 home runs and posted an OPS of .673, reaching free agency silently after the 2022 season.

2022: A-

The 2022 trade deadline was excellent for the Pirates. They only made two trades, but both deals worked out well. They traded three total players, all veterans with expiring contracts.

The first of the two deals involved sending designated hitter Daniel Vogelbach to the Mets in exchange for Colin Holderman. Holderman developed into one of the best relievers in the Pirates' bullpen, and all it took to obtain him was someone who couldn't play the field.

With the Pirates, Vogelbach had an OPS of .768 with 12 home runs and 34 runs batted in. He also had a solid on-base percentage of .338 and hit 10 doubles. He did even better with the Mets, increasing his OPS on the year to .793 with 18 total home runs. Although he did well for the Mets in 2022, he followed it up with a tough year in 2023; Vogelbach was not re-signed when he reached free agency.

The Pirates won this trade handily, as they received a solid reliever in return with lots of control on his contract. Holderman quickly became a setup man to David Bednar and is also having his best year in 2024. This season, Holderman has a 1.72 earned run average with a WHIP of 1.20 in 36.2 innings pitched and has struck out 45 batters. This was an excellent acquisition in 2022.

The other trade at the 2022 trade deadline was sending Jose Quintana and Chris Stratton to the Cardinals in exchange for Johan Oviedo and Malcom Nuñez. The Pirates found success with Oviedo, but Nuñez has not really developed and remains in Triple-A.

Quintana was very good with Pittsburgh prior to being dealt. Quintana had a 3.50 earned run average and a WHIP of 1.27. Stratton, on the other hand, had an earned run average of 5.09 and a WHIP of 1.55. The Pirates packaged these arms together to get two new players.

Oviedo was a great pickup by Cherington, as he was one of the best pitchers for the Pirates in 2023. He went 9-14 with an earned run average of 4.31 in 177.2 innings pitched and struck out 158 batters. After the season, he did have to get Tommy John surgery, which represents a big loss to the Pirates in 2024.

Nuñez, the second player in this deal, hit 17 home runs in the first half before coming to the Pirates, but has yet to hit double-digit homers in a season in the Pirates' organization. This year in Triple-A, Nunez has a .256 batting average with nine home runs and 43 runs batted in.

Overall, this trade deadline was very good for the Pirates. Holderman and Oviedo are big pieces to the Pirates' future, and all they cost were rentals.