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Many fans have mixed emotions about Pirates General Manager Ben Cherington. He obviously hasn't been perfect during his tenure in Pittsburgh, but no one in that role can boast perfection.
Right now, he is in his fifth offseason in that position, making this the perfect time to reevaluate his debut offseason and determine how well he performed.
Grading Ben Cherington's first offseason with Pirates: How does it look now?
All of his major league signings were all pretty mediocre, but that's somewhat expected when trying to start a rebuild. The shortened 2020 season didn't help either, but it also benefited the Pirates in a way.
Luke Maile: F
The Pirates signed Maile to a major league contract, and he was having a poor spring training before the delayed season. He ultimately did not play in 2020 after undergoing surgery on his finger. Either way, it was likely that he would not have been very productive after his spring showing, as well as the body of work he has provided in his entire career. Since he did not play in Pittsburgh, the move gets an F.
JT Riddle: D-
JT Riddle represented another one-year signing. He served as a utility option for the Pirates, and did not do well offensively or defensively. He had a wRC+ of two. The league average is 100. Yup.
On top of that, Riddle had an OPS of .398 and a batting average of .149. The only thing preventing him from an F grade was saving one defensive run across 48 innings in the outfield. This signing really did not bring any positives.
Guillermo Heredia: D
The last one-year deal that didn't make much of an impact was given to Guillermo Heredia. He played in just eight games with the Pirates, posting an OPS of .465 with a wRC+ of 36 and an fWAR of 0.1. That value came from solid defense in the outfield; he saved two defensive runs and produced a fielding run value of +1. He was designated for assignment for Carson Fulmer, who the Pirates just got back again, after that quick showing, but did leave Pittsburgh with a positive fWAR, giving him a grade of D.
Jarrod Dyson: C+
The only other major league free agent signing that offseason was Jarrod Dyson, and he made more of an impact to the Pirates organization than any of the other additions. His play on the field didn't exactly provide positive value, as he put up a .375 OPS and a wRC+ of six, but the White Sox decided to snag him off of the Pirates hands at the 2020 trade deadline.
What the Pirates got in return was international bonus pool money, which was used to help get one of the most underrated prospects in Pittsburgh's farm system in Po-Yu Chen. The right hander had a great year in Double-A, posting an earned run average of 4.03 with a WHIP of 1.29 and a walk rate of just 7.5%. Chen makes this signing worth it, despite Dyson's very poor showing in Pittsburgh, earning a grade of a C+.
The first offseason also included Ben Cherington's first big trade with the Pirates.
Starling Marte to Arizona for Liover Peguero and Brennan Malone: C
The only trade Cherington made during the 2020 offseason was sending Starling Marte to the Diamondbacks for a package of two prospects. This trade did not really work out for either team, as Marte played in just 33 games for Arizona before being sent to Miami at the ensuing trade deadline
The players the Pirates received in return have yet to make a significant impact on the organization. Liover Peguero has appeared in the major leagues for three straight seasons, belting seven home runs, producing a wRC+ of 73, and posting an OPS of .650. He still has a chance to compete for the starting shortstop job, but he struggled in Triple-A in 2024.
The other player was Brennan Malone, who has not pitched higher than Bradenton, as injuries have prevented him from pitching consistently. He was once a highly ranked prospect, but he has fallen due to his health.
Overall, Cherington's first offseason in Pittsburgh was not great, but it did result in a few players that could make an impact down the road. His free agent signings all ended up among the worst hitters in the league, and the big trade turned out mediocre.