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.