3 trades the Pirates wish they could do over in the Ben Cherington era

During Ben Cherington's tenure as general manager of the Pittsburgh Pirates, he has made a handful of questionable trades. While some may have turned out to positively impact the team in the end, most of them have not.

There are so many to choose from over the past five years, but let's go over three trades from the Cherington era that the Pirates wish they could do over.

Which three trades under Ben Cherington do the Pirates wish they could do over?

Trading Jameson Taillon to the New York Yankees

One of the big trades after Cherington's first season with the team was sending Jameson Taillon to the New York Yankees. The return was a package of four prospects, none of whom have benefited the Pirates in any way.

Miguel Yajure joined the Pirates first out of the four and did not perform well at all. In 2022, he posted an 8.88 earned run average in 24.1 innings pitched and had a WHIP of 1.93. He was later designated for assignment.

Two other players in this deal were also designated for assignment in 2024. Canaan Smith-Njigba had an OPS of .674 and hit two home runs in Triple-A before leaving the Pirates organization. Roansy Contreras was the other. He looked good in 2022, posting a 3.79 earned run average, but after the year, he was not effective, resulting in the Pirates moving on.

The only player still with the Pirates from this trade is Maikol Escotto, but he has not shown any upside in his three seasons in High-A Greensboro. He has been stuck in High-A and 2024 was his best season, batting .215 with eight home runs and a wRC+ of 73.

This trade turned out to be a complete failure. Trading Taillon was not a bad idea at the time as it benefitted the Pirates' rebuild, but the return did nothing to help the team improve.

Acquiring Jalen Beeks from the Colorado Rockies

For a rental, Jalen Beeks was a solid target to add another left hander to the bullpen, but he did not work out. On top of that, the prospect the Pirates gave up for made had a really strong first impression with the Colorado Rockies.

After joining the Pirates, Beeks threw 20.2 innings and posted an ERA of 3.92. Although that is not terrible, his WHIP was very high at 1.79, along with an opponent batting average of .311. He was completely ineffective at limiting baserunners, which defeated the purpose of acquiring him in the first place.

Luis Peralta, the player the Pirates sent back to Colorado in this deal, was much more productive at the Major League level down the stretch than Beeks. In 12.1 innings with the Rockies, Peralta delivered a 0.73 ERA with a WHIP .97 of and a FIP of 2.60. He was really impressive and could have benefited the Pirates more in not only 2024, but in the long run.

Trading Josh Bell to the Washington Nationals

Similarly to Taillon, the Josh Bell trade made a lot of sense for the Pirates organization at the time, but the players they got in return did not turn out at all.

Bell has not really had a season like his 2019 excellence, which made it the right time to move on after the 2020 season. In return, the Pirates got Wil Crowe and Eddy Yean from the Washington Nationals.

Crowe made his debut quickly but fizzled out and went to play overseas, and Yean spent three years in the lower levels of the Pirates' farm system and pitched badly in each of them. He did have a great turnaround in 2024, posting a 3.45 earned run average and a WHIP of 1.33 in Double-A, which is making this trade look a little better, but still is not good enough.

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