Grading the Pirates' trade deadlines under Ben Cherington

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.