Pittsburgh Pirates: Ranking Ben Cherington’s Trades

Ben Cherington has made a multitude of trades since taking over as Pittsburgh Pirates general manager. Let’s rank his biggest trades he’s made so far.

The Pittsburgh Pirates have been in a rebuild since the beginning of the 2019-2020 off-season. The rebuild started with multiple coaches and front office personnel being fired. The big moves were replacing former longtime manager Clint Hurdle with Derek Shelton, pitching coach Ray Searage with Oscar Marin, and the most notable, letting go of general manager Neal Huntington in favor of Ben Cherington.

Coming into the organization, Cherington had a very good resume on hand. He was one of the main driving factors who put together the Boston Red Sox World Series winning cores in 2013 and 2017, as well as the Toronto Blue Jays’ core that won 91 games this past season.

Cherington started the rebuild by trading off many of his veterans for top prospects, many of whom are considered top prospects, not just in the Pirate system, but in all of baseball. This has helped give the Pirates a very bright future. So which of his trades was the best?

To determine this, I narrowed it down to just the big trades. So while trading Jarrod Dyson for international bonus pool money from the Chicago White Sox ended with them signing Po-Yu Chen, I wouldn’t really classify this as a major trade. The main criteria for a ‘major trade’ is they played at least one full season in a Pirates’ uniform.

I’m also looking at trades that were given at least half of a season to develop. For example, after Adam Frazier was traded to the San Diego Padres, he struggled a lot having just an 85 wRC+ and 0.5 fWAR in 211 PA’s, but only in 211 plate appearances. Tucupita Marcano, the prospect who was considered the headliner in the deal, went straight from A-Ball to the major leagues. He likely needs more than just 50 plate appearances in the major leagues, or 412 plate appearances above Low-A to know what he is capable of. So far, the trade has looked like a complete wash.

I’m also taking into consideration how good the player who was traded performed after the swap. So if the player the Pittsburgh Pirates traded struggled post-trade, that would help the Pirates in their side of the swap.