Grading Pirates General Manager Ben Cherington’s Trades So Far

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.