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Grading Pirates General Manager Ben Cherington’s Trades So Far

Pittsburgh Pirates general manager Ben Cherington was hired after the 2019 season and went right to work making trades. He had the unenviable task of turning around a team that had just finished 69-93 and had a depleted farm system. Now in year five of this latest rebuilding program, the major league record, which stands at 21-26 as of this writing, should be better. On the other hand, the 2024 edition of the Pirates has more talent than the one Cherington inherited. Gone are the days when Colin Moran manned third base and Cole Tucker patrolled the outfield. The jury is still out on the trades made by Cherington in 2022-23. But we’re far enough along where we can evaluate his “rebuilding” trades of 2020-21 with the benefit of hindsight.

Grading the Trades of Pirates GM Ben Cherington

Cherington Trades the First of Pirates Stars

January 27, 2020: OF Starling Marte to Arizona Diamondbacks for P Brennan Malone and SS Liover Peguero. At the time, Marte was the Pirates’ best player. In eight years with Pittsburgh, he hit .287/.341/.452 with 108 home runs and 420 RBI. He’s the proverbial five-tool player, with speed and a strong arm. He was an All-Star in 2016 and a two-time Gold Glove Award winner. But he was reportedly unhappy in Pittsburgh and his occasional mental lapses were frustrating, as was his 2017 suspension for PEDs. Marte is now on his fourth team since the trade.

Malone was Arizona’s No. 9 prospect at the time. He’s been unable to stay healthy since he was acquired and hasn’t pitched since 2022. Peguero is currently at Triple-A Indianapolis. He’s had a taste of the majors and shown he can play good defense in the middle. He hit .239 with the Pirates with surprising power (7 homers in 201 at-bats). There’s no reason to think the bat won’t eventually come around. Grade: B-.

For Whom Bell Tolls (Not the Pirates)

December 24, 2020: 1B Josh Bell to Washington Nationals for P Wil Crowe and P Eddy Yean. Bell had a breakout season in 2019, hitting .277/.367/.569 with 37 home runs, 116 RBI, and a 142 OPS+. However, Cherington’s thinking was that by the time the Pirates were good, Bell wouldn’t be around anyway, and it was a good time to sell high. Since the trade, Bell has played for four teams in four years. Over that time, he’s hit .254/.341/.428 with 71 HR and 253 RBI as of this writing. Crowe wasn’t effective as a starter in 2021. Converted to the bullpen in 2022, he proved to be a reliable workhorse. Appearing in 60 games, he was a good eighth-inning option and often pitched multiple innings. His ERA was 3.12 as late as August 28, before he tired and saw it balloon to 4.38.

The Pirates quickly soured on Crowe in 2023 after just 9 2/3 innings. He now toils in Japan. Yean is still in the minors, where he has yet to distinguish himself. In the end, the Pirates should have gotten more for Bell. Better yet, they could have kept him. While he’s never matched his 2019 production, four more years of Bell would have been preferable to the Pirates’ revolving door of one-year rentals at first base. If the following grade seems generous, it’s because Crowe had the makings of a good reliever. We’re evaluating what the Pirates got, regardless of whether they foolishly gave up on him too soon. Grade: C.

Five For One

January 19, 2021: P Joe Musgrove to San Diego Padres for P David Bednar, P Omar Cruz, P Drake Fellows, CF Hudson Head, and C Endy Rodríguez. When the Philadelphia Phillies traded five players to get Von Hayes in 1982, Pete Rose nicknamed him “Five For One.” One could give Musgrove the same moniker. Of all the trades Cherington made for the Pirates, he had to hate this one the most. Musgrove is a solid starter and an all-around good guy. The Padres have since rewarded him with a long-term contract.

However, in Bednar, the Bucs have a two-time All-Star closer and a popular local product who’s active in the community. In Rodríguez, the Pirates have their catcher of the future, although he’s out for 2024 after undergoing offseason surgery. Cruz, Fellows, and Head have yet to play in the majors. Cruz is back in the Padres system. Fellows and Head are not highly ranked prospects, although Head once was. Bednar and Rodríguez were more than adequate as the return for Musgrove. Grade: A+.

Cherington Trades a Pirates Fan Favorite

January 24, 2021: P Jameson Taillon to New York Yankees for P Roansy Contreras, SS Maikol Escotto, OF Canaan Smith-Njigba, and P Miguel Yajure. Taillon was the Pirates’ No. 1 pick in the 2010 MLB June Amateur Draft. He’s an easy guy to root for. He’s a cancer survivor and has also had Tommy John surgery. Since leaving the Pirates, he’s pitched well, although more like a No. 3 starter than a first-round draft pick. Yajure was a highly regarded prospect who was thought to be the key to the deal. However, he floundered in brief trials in 2021 and 2022 with the Pirates. Today he pitches in Japan.

Contreras looked to have the makings of a staff ace. He joined the Pirates rotation on May 24, 2022. By July 7, he was 3-2 with a 3.78 ERA after a strong start in Cincinnati. That’s when the Pirates decided to shut him down for a bit of rest – and he hasn’t been the same pitcher since. The Pirates tried to get him right by putting him in the bullpen. Finally, they needed a roster spot when Carmen Mlodzinski came off the injured list, and Contreras was traded on Thursday. Smith-Njigba has appeared in 18 games with the Pirates. He and Escotto remain in the Pirates system. Grade: D.

Cherington Trades a Pirates All-Star

July 26, 2021: 2B Adam Frazier to the Padres for INF Tucupita Marcano, P Michell Miliano, and RF Jack Suwinski. The first 2021 deadline deal enraged Pirates fans. At the time, Frazier was hitting .324 and was the starting second baseman for the National League in the All-Star Game. The numbers crunchers said his batting average wasn’t sustainable due to a low hard-contact rate. The geeks got this one right. Since the trade, he’s played for four teams and has hit .240/.305/.339.

In 295 games so far with the Pirates, Suwinski hit .208/.312/.413 with 48 HR and 124 RBI. A higher average would be nice, but he did lead the Bucs in homers in 2023. Marcano spent time with the Pirates in 2022-23 but was sinking on the depth chart and is back with the Padres. Miliano never made it and now plies his trade in the Frontier League. No matter, Frazier for Suwinksi was a good swap for Pittsburgh. Grade: A.

The Yankees’ Revenge

July 26, 2021: P Clay Holmes to the Yankees for INF Diego Castillo and INF/OF Hoy Park. Consider this one the Yankees’ revenge for the A.J. Burnett trade in 2012. In four years with Pittsburgh, Holmes had a 5.57 ERA, no saves, and a 1.638 WHIP. Since coming to New York, he’s blossomed into one of the better relievers in baseball. Now in his fourth year as a Yankee, he has a 2.22 ERA, 57 saves, and a 1.034 WHIP. His former Pirates teammates weren’t surprised. To a man, they were quoted as saying he always had the stuff to succeed. The Pirates surely screwed up somewhere. Castillo and Park played for the Pirates but weren’t the answers to anything and are with different organizations now. Grade: F.

Cherington Was Busy with Pirates Trades at the 2021 Deadline

July 28, 2021: P Tyler Anderson to Seattle Mariners for C Carter Bins and P Joaquin Tejada. When Cherington signed Anderson, he was the proverbial veteran pitcher who would mentor the youngsters for a few months, then be dealt for prospects. The two players obtained have yet to appear in the majors. At 25, Bins is probably a wash by now. But Tejada is only 20. Let’s give this deal more time. Grade: Incomplete.

July 30, 2021: P Braeden Ogle to the Phillies for C Abrahan Gutierrez. When this was the first of many Pirates deadline day trades announced by Cherington, the reaction by Pirates fans was, huh? Neither party has appeared in the majors yet. Ogle now toils in the independent Atlantic League. The Bucs think highly enough of Gutierrez that they included him on the Spring Breakout Game roster. Grade: A.

July 30, 2021: P Richard Rodríguez to Atlanta Braves for P Ricky DeVito and P Bryse Wilson. Rodríguez became the Pirates’ closer in 2021 and was traded after garnering 14 saves. He pitched well for the Braves for two months but hasn’t pitched in the majors since. The Pirates tried Wilson as a starter during 2021-22, during which he was 4-13 with a 5.37 ERA. They made the unusual move of selling him to a division rival, the Milwaukee Brewers, in 2023. DeVito is no longer Pirates’ property. He has yet to appear in the big time and might be running out of time. Although Rodríguez fell off the map after 2021, Cherington should have gotten more for his closer. Grade: D.

July 30, 2021: P Austin Davis to Boston Red Sox for INF Michael Chavis. Davis was a disposable left-handed relief pitcher. Chavis had been a No. 1 draft pick of the Red Sox in 2014 when Cherington was there. Whatever Cherington saw in him then, he didn’t see it in Pittsburgh. Both parties to the deal are now with different organizations in the minors. Grade: C.

Cherington Trades Pirates Gold Glove Catcher

November 29, 2021: C Jacob Stallings to Miami Marlins for P Kyle Nicolas, OF Connor Scott, and P Zach Thompson. Here was another instance of Cherington selling high on a player. This time it was a Gold Glove Award winner. Stallings is now with the Colorado Rockies. Thompson pitched 29 games for the Bucs in 2022, going 3-10 with a 5.18 ERA and a 1.512 WHIP, before they parted company. Nicolas is a hard thrower with a history of wildness. He’s currently with the Pirates as a middle reliever. Over 2022-24 with the Pirates’ Double-A Altoona, Scott is hitting .222/.284/.349. Nicolas may yet pan out, but Cherington should have received more for a Gold Glove catcher. Grade: D.

The Last Word

Despite so few of these trades yielding great returns for the Pirates, Cherington has strengthened their farm system through the draft. We’ll need some time before we can evaluate his 2022-24 trades on these pages. Bet you can’t wait.


Photo Credit: © Charles LeClaire-USA TODAY Sports


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