Pittsburgh Pirates: Ben Cherington’s Yearly Report Card

Mandatory Credit: Charles LeClaire-USA TODAY Sports
Mandatory Credit: Charles LeClaire-USA TODAY Sports /
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PITTSBURGH, PA – OCTOBER 01: Michael Chavis #31 of the Pittsburgh Pirates in action during the game against the Cincinnati Reds at PNC Park on October 1, 2021 in Pittsburgh, Pennsylvania. (Photo by Joe Sargent/Getty Images)
PITTSBURGH, PA – OCTOBER 01: Michael Chavis #31 of the Pittsburgh Pirates in action during the game against the Cincinnati Reds at PNC Park on October 1, 2021 in Pittsburgh, Pennsylvania. (Photo by Joe Sargent/Getty Images) /


The first major trade Cherington made dating back to the beginning of the 2020-2021 offseason was Josh Bell. Bell was coming off a poor season and had been an extremely inconsistent batter throughout his time with the Pittsburgh Pirates. Not only could he ever find consistency, but he was also one of the worst defensive first basemen in baseball. The Bucs dealt him to the Washington Nationals for two prospects, that being Wil Crowe and Eddy Yean.

Crowe pitched 116.2 innings in the major leagues with the Pirates this year but had a poor 5.48 ERA, 5.67 FIP, and 1.569 WHIP. While the expectations for Crowe as a starting pitcher weren’t high, he could still develop into a back-of-the-rotation arm or swingman type reliever.

Yean spent the season at A-Ball Bradenton where he put up a 5.27 ERA, FIP, and 1.43 WHIP. While he did have a solid 23.3% strikeout rate and 1.08 HR/9, walks were his main issue (13.2%). Though he did have a strong 52.6% ground ball rate and displayed some solid stuff at Bradenton which gives hopes that he can rebound in 2022.

Yean will be 20 for about half of the 2022 season, so he still has time to figure things out. Bell turned things around in DC having a quality 118 wRC+ and 27 home runs. But he continued to display below-average defense at first base and only had a 1.4 fWAR.

The next major trade was Joe Musgrove to the San Diego Padres. Musgrove showed the talent to be a good starting pitcher but consistently ran into some bad luck, mainly because of poor defense on the Pirate end. The Pirates ended up getting back a four-player package for the right-hander.

While Hudson Head was considered the headliner at the time of the trade, you wouldn’t have guessed that based on Endy Rodriguez and David Bednar’s performances this year. The switch-hitting catcher, Rodriguez won the Low-A Southeastern League MVP after posting outstanding numbers.

Bednar, the Mars native, looks to open 2022 as the major league team’s closer. Head showed a strong ability to draw walks and hit for some power, but his swings and misses stood in the way of a good season. Though he’s still fairly young and is considered a high-ceiling, highly athletic outfielder. Omar Cruz pitched mostly at Double-A this year where he put up solid results. He’ll likely start 2022 at Triple-A Indianapolis and could make an impact at the major league level in 2022. The fourth and final player was Drake Fellows, who only pitched 11.2 innings between the FCL and Bradenton. He’s a forgotten man in the draft, but still a player to keep watch on in 2022.

The next big trade was when they sent Jameson Taillon to the New York Yankees. Despite Taillon coming off his second career Tommy John surgery and not pitching more than 150 innings just one time throughout his career up to the trade, the Pirates were still able to get back a four-player prospect package, one that could be a franchise changer.

The headliner at the time was Miguel Yajure. A control/command-oriented pitcher, Yajure showed off some solid stuff in the major leagues. He did have one big blow-up outing at the end of the year, but had it not been for an injury, he would have likely gotten an extended look in the major leagues this year. Roansy Contreras has developed into one of baseball’s most notable pitching prospects. The right-hander saw a huge uptick in velocity, going from the low-to-mid-90’s to the upper-90’s this year. Plus with a strong breaking ball, above-average change-up, and good command, he could be one of the Pirate standout starting pitchers.

Outfielder Canaan Smith-Njigba had a good season at Double-A and was promoted to Triple-A at the tail-end of the season. He could make an impact on the Major League team next season. Finally, there’s Maikol Escotto. The infielder showed off some promise at Low-A Bradenton, but only had a 100 wRC+. Still, he’s only 19-years-old and won’t turn 20 until next June. Escotto has very good power potential and has shown off a strong ability to draw walks. He just needs to strike out less and lower his ground ball rate. Taillon would go on to have just a 100 ERA+ and 2.0 fWAR. While not awful, he wasn’t any better than Tyler Anderson.

Approaching this year’s deadline, Cherington took advantage of Adam Frazier’s hot streak. Frazier was having a strong season at the time, but Frazier was showing signs of slowing down at the time of the trade with a .730 OPS and 100 wRC+ in the month leading up to the swap. Plus he had a high batting average on balls in play. The Bucs decided to deal the utility man to the San Diego Padres for a three-player prospect package.

The best prospect to come out of the deal was a utility prospect by the name of Tucupita Marcano. Marcano went directly from Low-A all the way to the major leagues from 2019 to 2021. He didn’t play at any other level before making his Major League debut, so it’s understandable why he struggled in his small sample size of plate appearances (50).

Still, Marcano has been highly praised by scouts for his hand-eye coordination and his ability to put the bat to the ball. He’s also shown a good ability to draw walks, along with avoiding strikeouts. Plus he’s athletic and can play multiple positions. Jack Suwinski is a power-hitting outfielder but does have his struggles when it comes to strikeouts. He has some sneaky athleticism which lets him move around well in the outfield while also having a strong arm. The last player involved was Michell Miliano. The right-handed relief prospect has a big fastball but struggles greatly with command. Though the Padres saw Frazier hit for just a .662 OPS and 85 wRC+ so far.

The other big trade around the deadline was Richard Rodriguez. Rodriguez, like Frazier, had a great start to the 2021 season but was showing signs of slowing down. He was one of the main pitchers affected by the crackdown on sticky substances, so with that, the Pirates moved him at the deadline for two pitching prospects; Bryse Wilson and Ricky DeVito.

Wilson was once one of Atlanta’s top 10 organizational prospects, even before the likes of Ronald Acuna Jr., Austin Riley, Mike Soroka, and Ian Anderson would graduate prospect status. Wilson showed some potential as a solid #4 starter during his time with the Pittsburgh Pirates so far but needs to show a better ability to go deeper into games. Ricky DeVito on the other hand had a good start to the 2021 season at Low-A but was held to just 20.1 innings because of an injury.

While DeVito doesn’t project as a top-of-the-line pitching prospect, there’s still a solid pitcher in the right-hander. Whether or not he’ll work out of the rotation or bullpen will remain to be seen, but he has shown off some good stuff, including an impressive splitter. Rodriguez post-trade saw a huge decline in effectiveness. While he did have a 3.12 ERA, that was supported by an extremely unsustainable .200 batting average on balls in play. He gave up 6 long balls in just 26 innings (2.08-per-9), walked 5, only struck out 9, and was even left off the Braves’ postseason roster.

The team also made a handful of smaller deals around the deadline. This included sending Tyler Anderson to the Seattle Mariners for Joaquin Tejada and Carter Bins, trading Austin Davis to the Boston Red Sox for Michael Chavis, and then moving Clay Holmes to the New York Yankees for Diego Castillo and Hoy Park.

While the Josh Bell trade doesn’t look good so far, the Joe Musgrove trade looks like it could be a win-win trade. The Taillon trade has the potential to be the Pirates’ version of the Archer trade (knock on wood). While I also think the Adam Frazier trade is blown way out of the water by some fans, it still feels like the team could have foregone either Suwinski and/or Millano for a slightly better headliner. The Rodriguez trade may be more of a forgotten deal, but the Pirates got two pitchers who have some potential for a reliever who’s struggled with command since losing the sticky stuff. I also think Cherington did well in the smaller trades. Getting anything for Austin Davis was a plus and Diego Castillo looks like he could be a starting infielder for the Pirates next season.

If you want a different prespective from the trades, the only player of high value that was traded (ie Bell, Musgrove, Taillon, Frazier), only Taillon’s team, the Yankees made the playoffs, albiet in the second Wild Card spot and lost to the Red Sox (unless you consider Rodriguez and the Braves who are on their way to the ALCS, but with him not part of the roster).

Grade: B
While he seems to have done very well on some trades, others have given the Pirates a less-than-favorable return so far. But none of the trades have been downright awful.