Pirates' Trades Under Ben Cherington

Grading the record.

Endy Rodriguez Photo Credit: WTM

Inspired by an article grading Ben Cherington’s trades while GM of the Red Sox, I decided to do the same with his trades for the Pirates. Obviously, it’s pretty early with some of these; I’m sure everybody can keep that in mind. I’m including every one I can find, so there’ll be a bunch of nothingburger deals that aren’t worth grading. If I don’t add any comments on a trade, nobody involved did anything afterward.

2020

OF Starling Marte to Arizona for RHP Brennan Malone, SS Liover Peguero, and international slot space. Marte has put up 11.2 bWAR since then. Malone and Peguero are both gone, having provided no value to the Pirates.
Grade: F

Cash to the Mets for RHP Tyler Bashlor. Bashlor got bombed in a handful of games.

RHP Joel Cesar to Philadelphia for LHP Austin Davis. Davis had a 4.73 ERA in 15 games for the Pirates, then went on to pitch badly for Boston. Cesar never got past AA.
Grade: C-

OF Jarrod Dyson to White Sox for international slot space. Dyson was awful before and after the trade.

1B Josh Bell to Washington for RHPs Wil Crowe and Eddy Yean. Bell’s been an oddly every-other-year sort of player, but he has hit 107 home runs since the trade. Crowe had a 5.03 ERA with the Pirates, and Yean is gone now without having reached the majors.
Grade: F

2021

In a three-team trade, sent RHP Joe Musgrove to San Diego, and received RHPs David Bednar and Drake Fellows, LHP Omar Cruz and OF Hudson Head from the Padres, and C Endy Rodriguez from the Mets. Musgrove went 37-24, 3.20 for the Padres. Bednar became a very good, at times elite, closer. Rodriguez remains in the “you’re-saying-there’s-still-a-chance?” category. The others did nothing.
Grade: B

RHP Jameson Taillon to the Yankees for RHPs Roansy Contreras and Miguel Yajure, IF Maikol Escotto, and OF Canaan Smith-Njigba. Taillon’s been a good starter for five years. The Pirates got nothing from the trade beyond a lot of false hope with Contreras.
Grade: F

Cash to Oakland for OF Dustin Fowler. Fowler hit .171 in 18 games with the Pirates.

IF Shendrik Apostel to Cubs for RHP Duane Underwood, Jr. Apostel, a rookie-level player, disappeared almost immediately after the trade. Underwood had a 4.49 ERA in 114 games as a reliever with the Pirates.
Grade: C+

Cash to Angels for RHP Kyle Keller. Keller was terrible over 32 games with the Pirates.

RHP Edgar Santana to Atlanta for cash. Santana had a 3.59 ERA in 41 games for the Braves in 2021, then got hurt and pitched only in foreign leagues after that. The Keller and Santana deals were four days apart, so if you count the two deals as Santana-for-Keller, you have an F.

OF Jose Berroa to Baltimore for C Taylor Davis. Davis played in two games for the Pirates.

RHP Jandel Gustave and OF Troy Stokes, Jr., to Milwaukee for C Samuel Escudero. Gustave pitched decently in 41 games for the Brewers. Escudero is still in rookie ball.
Grade: D

Cash to St. Louis for 1B John Nogowski. In 33 games with the Pirates, Nogowski had an OPS+ of 84. These nothingburger deals were seemingly the only thing going on with the Pirates for a long time.

IF Kevin Kramer to Milwaukee for LHP Nathan Kirby. And another one. Neither guy played in the majors afterward.

IF Adam Frazier to San Diego for RHP Michell Miliano, IF Tucupita Marcano, and OF Jack Suwinski. Frazier declined quickly after the trade, but he had good value at the time. Still, for a bit, Suwinski made the trade look like a win, but he’s been a burden for the last two years. Marcano played badly in the majors, then got banned for gambling. Miliano never got past AA.
Grade: C

RHP Clay Holmes to the Yankees for IFs Hoy Park and Diego Castillo. Park and Castillo both flopped with the Pirates. Holmes has been a very good pitcher, first as a closer and then as a starter.
Grade: F

LHP Tyler Anderson to Seattle for C Carter Bins and RHP Joaquin Tejada. Anderson pitched OK for Seattle as a rental. Bins never reached the majors and is out of baseball. Tejada has mostly been hurt and has only three appearances above rookie ball.
Grade: D

RHP Richard Rodriguez to Atlanta for RHPs Bryse Wilson and Ricky DeVito. Rodriguez had been a very good reliever with the Pirates for three and a half years, and pitched well the rest of that year for the Braves. He then got a PED suspension and suddenly disappeared. DeVito never reached the majors. Wilson pitched badly for the Pirates for about a year.
Grade: D-

LHP Braeden Ogle to Philadelphia for C Abrahan Gutierrez. Neither reached the majors.

LHP Austin Davis to Boston for IF Michael Chavis. Both were bad after the trade, Chavis a bit worse.
Grade: C-

IF T.J. Rivera to Philadelphia for cash.

C Jacob Stallings to Miami for RHPs Zach Thompson and Kyle Nicolas, and OF Connor Scott. Stallings fell off sharply both offensively and defensively after the trade, although as a Gold Glover with a passable bat he had significant value. Thompson was terrible, and Scott flopped. Nicolas still looks like he could be a late-inning reliever if he just throws a few more strikes.
Grade: C+

2022

RHP Listher Sosa to Arizona for IF Josh VanMeter. VanMeter was awful. Sosa never reached the majors, which was a much better outcome than giving VanMeter 192 plate appearances.
Grade: F

RHP Adonis Medina to the Mets for cash.

Cash to Cleveland for IF Yu Chang. Chang hit .167 in 18 games.

Cash to Cubs for LHP Eric Stout. Stout had a 5.79 ERA in 18 games. More and more nothingburgers.

LHP Anthony Banda to Toronto for cash. Banda wasn’t good for the Pirates and did little for a year and a half after this deal. Then he emerged as an effective reliever for the Dodgers in 2024-25, which is the sort of random thing that happens with relievers. (See Santana, Dennis.)

Cash to Yankees for RHP Manny Banuelos. Banuelos had a 4.96 ERA in 31 games for the Pirates.
Grade: C-

Cash to Cleveland for RHP Yohan Ramirez. His first go-round with the Pirates, Ramirez had a 3.67 ERA over 48 games. He’s had a very erratic career, but most of his better pitching has come with the Pirates.
Grade: B

1B Dan Vogelbach to the Mets for RHP Colin Holderman. Vogelbach had a big couple of rental months for the Mets. Holderman had some very good stretches for the Pirates, but couldn’t stay healthy, then mysteriously just lost it in 2025.
Grade: B+

C Michael Perez to the Mets for cash.

Cash to Toronto for RHP Jeremy Beasley. Beasley never pitched for the Pirates.

LHP Jose Quintana and RHP Chris Stratton to St. Louis for RHP Johan Oviedo and IF Malcom Nunez. Quintana was great as a rental for the Cards and has continued to pitch very well when healthy. Stratton also pitched very well for the Cards. Nunez hasn’t reached the majors and is now gone. Oviedo missed a ton of time with two injuries, but looked very promising as a starter, enough to get the Pirates Jhostynxon Garcia and a very interesting, low-level pitcher. This and the Vogelbach deal were the rare rental-for-prospects trades that seem to have gone well for both sides.
Grade: B+

Cash to Philadelphia for IF Drew Maggi.

RHP Jack Hartman to Tampa Bay for 1B Ji-Man Choi. Choi hit some home runs but was mostly hurt. Hartman is in AA and looks like a possible prospect.
Grade: D+

IF Kevin Newman to Cincinnati for RHP Dauri Moreta. Newman has been a decent utility IF. Moreta pitched well in 2023, had TJ and missed 2024, then pitched pretty well after returning in 2025. Oddly, the Pirates seemed to lose interest in him even though he pitched better than relievers they hung onto. The trade gets a good grade, the team’s handling of Moreta after his return gets an “F.”
Grade: B+

IF Hoy Park to Boston for LHP Inmer Lobo. Lobo is a low-minors version of Jamie Moyer. He gets good results and is amusing to watch if you have gun readings, but I don’t know how he’ll do past class A.

RHP Nick Garcia to Colorado for UT Connor Joe. Garcia has pitched well at times in the minors, but struggled in AAA in 2024 and got hurt in 2025. Joe had a 99 OPS+ in 256 games with the Pirates, which would have made him their third-best hitter in 2025.
Grade: B-

IF Diego Castillo to Arizona for RHP Scott Randall.

2023

RHP Bryse Wilson to Milwaukee for cash. Wilson had a very good year as a reliever for the Brewers in 2023, then a decent season in 2024.
Grade: F

RHP Zach Thompson to Toronto for OF Chavez Young.

RHP Ricky DeVito to Texas for IF Mark Mathias. Mathias had a 74 OPS+ in 22 games with the Pirates.

C Tyler Heineman to Toronto for IF Vinny Capra. Heineman put up a .777 OPS as a backup catcher for the Jays in 2025. That was after going to Boston and then back to the Jays, playing little in between, so it doesn’t go on the ledger for this deal. Capra went 3-for-18 for the Pirates.

RHP Robert Stephenson to Tampa Bay for IF Alika Williams. The Pirates totally misevaluated Stephenson. He immediately emerged as an outstanding reliever for the Rays for most of 2023, although he missed 2024 and part of 2025. Williams is a glove-only, AAA depth guy whom the Pirates just released.
Grade: F

Cash to the Dodgers for RHP Andre Jackson. Jackson pitched passably over the rest of 2023, then moved on to Japan.

1B Carlos Santana to Milwaukee for IF Jhonny Severino. Santana hit well as a rental for the Brewers. Severino has shown power potential, but can’t make contact nearly often enough. I’m not inclined to be too harsh about a trade involving a non-first-tier rental for a lottery ticket because that’s just how it goes.
Grade: C-

1B Jiman Choi and LHP Rich Hill to San Diego for OF Estuar Suero, 1B Alfonso Rivas, and LHP Jackson Wolf. Choi and Hill were terrible for the Padres and have since done nothing. Rivas was just a placeholder. Wolf was a prospect who flopped surprisingly quickly. Suero is a very toolsy outfielder who struggled at the plate for two years in rookie ball, then suddenly (like, very suddenly) started to hit late in 2025. Maybe the weirdest of all these trades, this one turned into a giant sinkhole apart from one still unexpired lottery ticket.
Grade: B-

IF Rodolfo Castro to Philadelphia for LHP Bailey Falter. Castro went 3-for-30 with the Phillies. He’s now heading overseas. Falter went 17-16, 4.32 for the Pirates in 296 innings.
Grade: A-

RHP Cody Bolton to Seattle for cash. Bolton pitched passably in 17 games for the Mariners.

Cash to Atlanta for LHP Marco Gonzales. This was a salary dump for the Braves, who’d just gotten Gonzales in a salary dump. He pitched not very well in seven starts for the Pirates and was mostly hurt, which, given his history, was easily predictable.
Grade: D-

Cash to Yankees for OF Billy McKinney. McKinney went 5-for-25 for the Pirates.

IF Deivis Nadal to Kansas City for OF Edward Olivares. Nadal was a low-level UT player who lasted only one more year in class A. Olivares had a 75 OPS+ and was well below replacement level for the Pirates.
Grade: D-

2024

RHP J.T. Brubaker to Yankees for IF Keiner Delgado. The Yankees took a chance on Brubaker’s health. He returned in 2025 and pitched decently, but in only 17 games, the last five with the Giants. Delgado’s shown a lot more swing-and-miss than expected, but he had a 124 wRC+ for Greensboro in 2025, and has both defensive and baserunning value.
Grade: B+

RHP Austin Strickland to San Francisco for C Joey Bart. This was functionally the equivalent of a waiver claim after Bart had been dfa’d. Strickland hasn’t distinguished himself in class A. Bart, meanwhile, had a surprising surge for the Pirates in 2024 and, despite a puzzling loss of power, still put up average hitting numbers in 2025.
Grade: A

LHP Jackson Wolf to San Diego for IF Kervin Pichardo. Wolf has struggled in AAA. Pichardo is a AA UT guy who’s moved on. Of the two, Wolf has the better, albeit limited, chance of ever doing anything.
Grade: C-

RHP Colin Selby to Kansas City for LHP Connor Oliver. Selby moved on to Baltimore and pitched decently in 11 major league games in 2025. Oliver appears to be a low-minors UT pitcher, which the Pirates needed due to pitching shortages in the system the last couple of years.
Grade: D

IF Sergio Alcantara to Arizona for cash.

OF Rodolfo Nolasco to San Francisco for RHP Daulton Jeffries. Jeffries threw a few innings for the Pirates.

RHP Roansy Contreras to the Angels for cash. Contreras has been doing the waiver pong thing since then.

Cash from Minnesota for Yoyner Fajardo. Fajardo hit .300 for Altoona, but he’s in Indy ball now.

Cash from Dodgers for LHP Jose Hernandez. Hernandez didn’t pitch well for the Dodgers in AAA.

Cash from Cubs for OF Gilberto Celestino. Celestino is a AAA depth guy.

LHP Luis Peralta to Colorado for LHP Jalen Beeks. The Pirates should have just kept Peralta. He pitched better the rest of the year in the majors than Beeks did, although he fell apart in 2025. Beeks moved on as a free agent.
Grade: D

RHP Quinn Priester to Boston for IF Nick Yorke. Priester ended up with Milwaukee and had a big 2025 season. Yorke started a mystifying trend of the Pirates trading for hitters and immediately losing interest in them. He hasn’t done well in limited major league chances and had a 104 wRC+ in AAA in 2025, which is uninspiring for a bat-first player.
Grade: D

IF Charles McAdoo to Toronto for IF Isaiah Kiner-Falefa. McAdoo struggled in AA for a while with Toronto, but had a good second half in 2025. Despite being credited by some Pirate fans as being a solid pickup, IKF was replacement level in 2024 and ranked 30th of 31 MLB shortstops with 400+ plate appearances in fWAR in 2025. He also took up 9% of the Pirates’ puny payroll.
Grade: D

RHP Patrick Reilly to Baltimore for OF Billy Cook. Another acquisition in whom the Pirates immediately lost interest, Cook hasn’t hit as hoped in the majors or minors, and he’s now 27. Reilly pitched well in A+ and AA in 2024, then was hurt for most of 2025.
Grade: D

IF Garret Forrester and RHP Shun-Seok Shim to Miami for OF Bryan De La Cruz. Forrester is a non-prospect whom the Pirates overdrafted in the 3rd round. Shim had great stuff but has imploded due to shoulder problems. De La Cruz was Ben Cherington’s big attempt to add offense at the 2024 deadline, but he was MLB’s worst player after the trade, based on fWAR, and it wasn’t very surprising. Taking context into account, it was one of Cherington’s biggest blunders.
Grade: F

LHP Martin Perez to San Diego for LHP Ronaldys Jimenez. Another rental-for-lottery-ticket deal, Perez pitched very well for the Padres. Jimenez is a rookie-level lefty with great stuff who needs to throw more strikes. As these things go, it wasn’t a bad effort and could still bear fruit.
Grade: B-

LHP Nicolas Carreno to Mets for LHP Josh Walker. Walker pitched poorly in eight games for Indianapolis, then left as a free agent. Carreno pitched poorly in rookie ball for the Mets. It’s not terribly clear what the point was with this one.

Cash to Cleveland for RHP Peter Strzelecki. Strzelecki pitched badly in AAA and was released.

In a three-team trade, sent RHP Luis Ortiz, and LHPs Josh Hartle and Michael Kennedy to Cleveland, and got 1B/2B Spencer Horwitz from Toronto. Hartle and Kennedy still have promise. If not for Ortiz’s legal problems, this trade might favor the Guardians. Horwitz lacks standard 1B power, but he was easily the Pirates’ best hitter in 2025, in fact, their only good hitter.
Grade: B+

RHP Joe Vogatsky to Boston for IF Enmanuel Valdez. Valdez only had an 82 OPS+, but he just got into 31 games before getting hurt for the year. The Pirates, being the Pirates, miscast him as a 1B, replacing the injured Horwitz. He has a history of being a solid hitter, so he could be a useful bench bat. Vogatsky was just OK in his first pro season, but had a good K rate. Hard to say much about this one yet.
Grade: B-

2025

Cash to Toronto for RHP Brett de Geus. De Geus was lost on waivers a few weeks later.

Cash to Mets for OF Alexander Canario. This was a typically aimless Pirate episode. After Derek Shelton said Canario needed ABs against major league pitching, he apparently forgot Canario was on the team. Don Kelly gave him some playing time and he started to hit, then he had a stretch of 50 games in which he got just 25 ABs and one hit. The Pirates stuck with him all year while he put up a 70 OPS+, then non-tendered him. Baffling.
Grade: F

C Jason Delay to Atlanta for cash.

OF Bryce Johnson and cash to San Diego for C Brett Sullivan. Johnson, a career AAA depth outfielder, hit .342 in 55 games with the Padres, which clearly was a small sample size phenomenon. Sullivan, also a AAA depth player, got into three games with the Pirates.

RHP Hunter Stratton to Atlanta for OF Titus Dumitru and cash. Dumitru put up a 117 wRC+ for Greensboro when he wasn’t busy defending the gates of Budapest from the Mongol hordes. Stratton pitched well in limited time with the Braves, both in AAA and the majors.
Grade: C

IF Adam Frazier to Kansas City for IF Cam Devanney. Frazier hit surprisingly well as a rental for the Royals. Devanney was yet another hitter the Pirates seemed to lose interest in as soon as they got him. He didn’t hit nearly as well in AAA as he had for the Royals, then looked very badly overmatched in 38 PAs in the majors. The Pirates released him after the season.
Grade: D-

3B Ke’Bryan Hayes and his salary to Cincinnati for SS Sammy Stafura, LHP Taylor Rogers, and cash. Hayes got off to a hot start with the Reds but quickly turned back into Hayes. Stafura looked good with the glove in class A, but not with the bat. The Pirates quickly ditched Rogers. This was a salary dump.
Grade: C+

LHP Caleb Ferguson to Seattle for RHP Jeter Martinez. A rental-for-lottery-ticket trade. Ferguson did what he does, pitching solidly in relief for the Mariners. Martinez didn’t pitch much for the Pirates as they worked with him on his motion. He has very good stuff and will either throw more strikes or not. Not much to say about this one yet.
Grade: B-

LHP Taylor Rogers for OF Ivan Brethowr. This trade was probably worked out before the Hayes deal. Veteran reliever Rogers didn’t pitch very well for the Cubs. Brethowr was in his first full season. He drew a ton of walks for Greensboro but, despite being a huge guy, didn’t hit for much power. If he and Dumitru both make the Pirates’ outfield, they’ll have the best-named outfield in MLB, no matter who else is in it.
Grade: C+

RHP David Bednar to Yankees for C/1B Rafael Flores, C Edgleen Perez and OF Brian Sanchez. Flores has power but questions about his contact ability and his chances of staying behind the plate. Perez is a young, athletic catcher, similar to Endy Rodriguez at the time except he hit just .204 with no power at all in class A. Sanchez was hurt at the time of the trade and didn’t play the rest of the year. He looks like he could potentially be a fourth outfielder. Given the prices that top relievers have been getting both at the deadline and in free agency, the Pirates should have gotten somebody with a higher ceiling in the deal.
Grade: D+

LHP Bailey Falter to Kansas City for LHP Evan Sisk and 1B Callan Moss. Falter was having a surprisingly good year for the Pirates, but got bombed in four games with the Royals and then went out with an injury. Sisk is a pretty fungible AAA reliever who reached the majors at age 28, but he pitched decently for the Pirates in 14 games. Moss really mashed with Greensboro after the trade, but as an undrafted college player, we need to see how he does in AA.
Grade: B-

C Eli Wilson to San Diego for cash.

RHP Johan Oviedo, C Adonys Guzman, and LHP Tyler Samaniego to Boston for OF Jhostynxon Garcia and RHP Jesus Travieso. No results yet from this one, but it looks like value for value, filling needs for both teams. Oviedo is a potential mid-rotation starter, but comes with health risks. Garcia is a potential power-hitting outfielder with some defensive ability and contact risk. Guzman’s defense is well regarded, and some scouts think he could be a latecomer with the bat. Samaniego could be a middle reliever as soon as 2026. Travieso is a lottery ticket, maybe a bit more promising than the usual. He has very good stuff despite a lack of size, and needs control improvements.
Grade: B+

RHP Tyler Baumler to Texas for RHP Jaiker Garcia. The Pirates arranged this before selecting Baumler in the Rule 5 draft. He doesn’t look like a great R5 candidate. Garcia is a lottery ticket. I’d probably rather have Garcia, but this could be a nothingburger deal.

In a three-team trade, sent RHP Mike Burrows to Houston and received 2B Brandon Lowe, OF Jake Mangum and LHP Mason Montgomery from Tampa Bay. This could be a very volatile trade. Burrows is a potential mid-rotation starter with injury risk. Lowe has power that the Pirates desperately need and will be a left-handed, dead-pull hitter in PNC Park, but he’ll be gone after a year, and he gets hurt literally every year. Mangum looks like an actual major league outfielder, nearly an unheard-of thing on a Cherington team. Hopefully, the Pirates will see him as a fourth outfielder and not a starter. Montgomery has control issues, but he has the ability to be a late-inning reliever and could conceivably make the trade from the Pirates’ standpoint.
Grade: B+

2026

RHP Chase Shugart to Philadelphia for C/IF Francisco Loreto. Shugart pitched well in 35 games for the Pirates in 2025, but for some reason got shuttled aside for Yohan Ramirez. Loreto is a low level lottery ticket who at least appears to have some power. No results yet, so standard lottery ticket grade.
Grade: C+