Williams: Ben Cherington’s Pittsburgh Pirates Trade History

Another trade deadline has passed, and for the fourth season in a row, the Pittsburgh Pirates were sellers at the deadline under General Manager Ben Cherington.

When Cherington took over, it was obvious that this team needed a complete tear-down rebuild, and a new focus. This week, I’m going to be evaluating the results so far from this rebuild.

That process begins today with a look at Cherington’s trade history with the Pirates. I won’t be looking at minor moves, but the ones aimed at impacting this rebuild process.


I’ll be breaking this article up into three sections. The first group of trades looks at guys who were expected to get a bigger return. These were the guys who the Pirates had to give their farm system a boost. It wasn’t a big group.


The trade that started the rebuild sent Starling Marte to the Diamondbacks for Liover Peguero and right-handed pitcher Brennan Malone. Marte had two years of control remaining, and went on to sign a four year, $78 million deal in 2022.

Current Status: Peguero is now in the majors in his age-22 season. He only has 30 plate appearances this year, but has three homers in that stretch, including a big one in Tuesday night’s win. It’s too early to say what Peguero can do, but he’s got some of the best talent and upside in this system. He should be given regular playing time going forward.

Chance to Improve: Malone has dealt with injuries, and has only pitched 19 innings since the trade. This deal will rely on the production from Peguero. He’s the type of player who can singlehandedly turn this into a win. The Pirates also received international money in this deal, which allowed them to sign outfielder Solomon Maguire. I wouldn’t include him in the return, but he’s adjacent to the return.


On Christmas eve, after not really making many moves the first season under Cherington, the Pirates traded Josh Bell to really begin their rebuild. Returning from the Washington Nationals were right-handed pitchers Wil Crowe and Eddy Yean. Bell’s value was low at the time, coming off a replacement level performance.

Current Status: The Pirates designated Crowe for assignment on July 21st this year. He combined for a 5.03 ERA in 202.1 innings as a swingman pitcher. Bell followed the trade with back-to-back 1.9 fWAR years, and signed a two-year, $33 million deal last offseason.

Chance to Improve: Eddy Yeah is currently in High-A Greensboro for the second year. He has a 5.55 ERA in 35.2 innings as a reliever in his age 22 season. Outside of an extreme revival for Yean, this deal is going to go into the books as a loss.


This deal might end up being the best one that Cherington made. It also was what really kicked off the rebuild. The Pirates traded Musgrove to San Diego, receiving David Bednar, Omar Cruz, Drake Fellows, and Hudson Head from the Padres. They also received Joey Lucchesi, a 27-year-old lefty pitcher at the time. He was flipped to the Mets for Endy Rodriguez, wrapping up the three team deal.

Current Status: Bednar is the closer in Pittsburgh, and one of the best in the game right now. Rodriguez has emerged as the starting catcher in Pittsburgh. Similar to Peguero, it’s very early in his MLB career, but the results have been promising.

Chance to Improve: This trade has the makings of an easy win. Bednar has been a lights out closer. Endy emerged as the top prospect in the system, and could be an essential spark in the 2024 and beyond seasons. Cruz might have a chance to make the majors as a lefty reliever, but has a 5.33 ERA in 27 innings in that role with Altoona. Fellows has been rehabbing an injury in the lower levels. Head is in his second season as an outfielder for Greensboro, and while he’s shown the best remaining potential of the group, he’s currently injured. The Pirates could get another 40-45 grade guy in this deal, but Endy/Bednar give this a chance to be an easy win.


Following the Musgrove trade, the Pirates dealt Jameson Taillon to the Yankees, getting four players in return. The most notable is Roansy Contreras, who has pitched in the majors, but is currently in the FCL doing development work after struggled in the big leagues this year. They also received right-handed pitcher Miguel Yajure, outfielder Canaan Smith-Njigba, and middle infielder Maikol Escotto.

Current Status: The best chances for production right now come from Contreras and Smith-Njigba. It’s only the age 23 season for Contreras, and he’s got the stuff to be a starter in the majors. In 166.1 innings in the majors, he has a 4.87 ERA. Smith-Njigba could factor into the outfield mix, with a chance to eventually developing into a role off the bench, with occasional starts.

Chance to Improve: Yajure is already gone, after combining for an 8.69 ERA in 39.1 innings. Escotto has a lot of raw power, but has yet to show an ability to hit, with a .208 average and a .266 OBP in High-A this year. He’s only 21, Contreras is 23, and Smith-Njigba is 24. This trade doesn’t look good right now, but there’s enough youth and talent to revive it, mostly from Contreras.


The Pirates dealt Adam Frazier to the Padres — a favorite trading spot for Cherington — getting Jack Suwinski, Tucupita Marcano, and Michell Miliano. The Pirates sold high on Fraizer, dealing him in a 3.6 WAR year. He’s followed with 1.5 WAR so far since the start of the 2022 season.

Current Status: The development of Suwinski might make this deal one of the best under Cherington. Suwinski has emerged as a starter the last two seasons, putting up a 1.7 WAR in his rookie year in 2022, and already a 2.4 WAR this season. He’s hit 40 homers in those two years, and could very well reach 30 this season. Marcano has also shown the ability to be a bench player in the majors, but is currently out for the year with a knee injury.

Chance to Improve: This trade is already a win, due to Suwinski. He’s also in his age 24 season, and continues showing signs of improvement. Marcano can give the Pirates a 45-grade bench player who can start on occasion all over the field. Miliano is pitched in High-A as a reliever in his age 23 season. He has a 3.86 ERA in 44.1 innings, with a 12.4 K/9 and a 5.3 BB/9.


The Pirates also sold high on Jacob Stallings. Following a 2.5 WAR season where he won a Gold Glove, he was traded to the Marlins for Zach Thompson, Kyle Nicolas, and Connor Scott. He’s since been below replacement level for Miami.

Current Status: Thompson pitched 121.2 innings last year in the majors, posting a 5.18 ERA. He was released at the start of this season. Nicolas and Scott are the drivers of this deal going forward. Nicolas is currently pitching in Triple-A, showing starter potential held back by control issues. Scott is in Double-A for the second season, batting .201/.256/.328.

Chance to Improve: Nicolas and Scott could both emerge as long-term 45+ grade players in the majors. Nicolas could be a swingman pitcher and Scott could be an outfielder off the bench who can play all three spots. 


This group of players provided that 40-45 value range. You’re not going to get a lot in return for this level of player. The Pirates have been hit or miss so far in this level of move, with the return values being low across the board.


The Pirates sold low on Clay Holmes, sending him to the Yankees, where he has since been a successful reliever. They received Diego Castillo and Hoy Park, who each had bench upside at the time.

Current Status: Castillo and Park aren’t in the system, and Holmes has a 2.21 ERA in 40.2 innings with the Yankees, making $3.3 million in his second year of arbitration. The Yankees have him for one more season.

Chance to Improve: None. I didn’t understand this trade then, and it makes less sense now.


Richard Rodriguez had a 2.98 ERA in 196.1 innings with the Pirates across four seasons. The Pirates dealt him to the Braves for Ricky DeVito and Bryse Wilson, and he hasn’t pitched since the end of the 2021 season.

Current Status: Neither Wilson nor DeVito are in the system. The Pirates traded DeVito for Mark Mathias, lost Mathias on waivers, and Mathias was just traded again yesterday in the A.J. Pollock deal between the Giants and Mariners.

Chance to Improve: None. DeVito was a live arm with good stuff, but the Pirates used him to get a bench infielder for a few months.


The Pirates tried to get Abrahan Gutierrez in an earlier deal, which fell apart. They went back to the Phillies and swapped minor league reliever Braeden Ogle.

Current Status: Ogle and Gutierrez are both playing for Altoona right now, after the Pirates re-signed Ogle. Gutierrez is currently on the injured list.

Chance to Improve: Gutierrez has a chance to be an MLB backup catcher. Getting him for essentially nothing in the long run was a small gift.


Signaling a future change for the middle infield, the Pirates dealt Kevin Newman last offseason for reliever Dauri Moreta. This move could make up for the loss of Holmes, with Moreta looking like he’s got the potential to be a shut down reliever.

Current Status: Moreta has a 3.50 ERA in 46.1 innings with the Pirates, along with a 12.2 K/9 and a 3.9 BB/9.

Chance to Improve: The Pirates have Moreta under team control through the 2028 season. Newman wasn’t going to be part of this team’s future, but Moreta could be a late inning reliever on the next winning team.


The Pirates didn’t add much to their team in 2020. They started adding free agents who could be flipped at the deadline in 2021. As a rebuilding team, they had the opportunity to add value free agents and flip them for players with long-term value. A few of these moves are looking more promising than the fringe section above.


After trading for Endy Rodriguez at the start of the year, and drafting Henry Davis first overall, the Pirates continued their catching focus with the Tyler Anderson trade. After seeing a deal fall apart with the Phillies involving Abrahan Gutierrez, they dealt the rental Anderson to Seattle, getting back Carter Bins and Joaquin Tejada.

Current Status: Bins is a solid defender and has a chance to be an MLB backup. Tejada has been pitching in the FCL this year, showing extreme control issues out of the bullpen in his age 20 season.

Chance to Improve: The hope here would be that Bins develops into an MLB backup. That’s a low return, and lower than what the Pirates got in following years.


Like the Newman trade that would follow, this deal could end up being shrewd. Daniel Vogelbach filled the first base hole in Pittsburgh for a few months in 2022, then was dealt to the Mets straight up for Colin Holderman.

Current Status: Holderman has a 3.57 ERA in 35.1 innings in relief this year, mostly working as David Bednar’s setup man.

Chance to Improve: Like Moreta, Holderman could be one of the shutdown relievers for a future winning team.


Jose Quintana was brought in as a rental pitcher in 2022, and put up strong results at PNC Park. Chris Stratton was thrown into a deal, and the Pirates received Johan Oviedo and Malcom Nunez from the division rival Cardinals.

Current Status: Last night’s game really underscored this move. Oviedo has a 4.42 ERA in 124.1 innings, which is league average production. He allowed one run in seven innings last night, showing an ability to be better than average in his age 25 season.

Chance to Improve: Oviedo is under team control through the 2027 season. Malcom Nunez could factor into the first base mix during the final two months of the season.


For a recap of this year’s moves — which saw Carlos Santana, Rich Hill, Ji Man Choi, Austin Hedges, and Rodolfo Castro traded — check out today’s Pirates Prospects Daily.

Pirates Prospects Daily: Recapping the Pirates Trade Deadline Moves

Check back later this week for part two of the rebuild evaluation, as I review the Pirates’ MLB draft history under Cherington.

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Tim is the owner, producer, editor, and lead writer of PiratesProspects.com. He has been running Pirates Prospects since 2009, becoming the first new media reporter and outlet covering the Pirates at the MLB level in 2011 and 2012. His work can also be found in Baseball America, where he has been a contributor since 2014 and the Pirates' correspondent since 2019.

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Generally , rebuilds return mediocre results. And it appears this rebuild will too. We are 4-5 years in and there is no sure end in sight. The cost is years and years of awful baseball and last place finishes.


I’m not sure how in aggregate these trades can be considered as anything other than mediocre. Cherrington had a fair amount of ammunition to deal in my opinion and the overall return is middling at best.


At the very least, it’s extremely hard to say how this success rate demonstrates any amount of tangible player dev improvement.


Maybe I’m being too hard(and heaven knows I’ve tried to be optimistic) but the development looks somewhere in between bad and terrible to me.


I tend to think these things fit into a Bell curve. Relatively few clubs are truly terrible, and relatively few clubs are exceptional.

The Pirates were firmly in the middle under Huntington – his developmental failures were not at all remarkable relative to the league, just far from exceptional – and Cherington certainly has done nothing to push them ahead of that range. Which was the entire reason he was hired and allowed a disastrously long teardown and rebuild.


The Peguero for Marte trade has a long, long way to go and its doubtful that it’ll be a win. Marte is one of the best players that the Pirates produced all time from their system. Long, productive career. This trade will go down as a loss.


Really depends on how you define win. If by win you simpmly mean got the better end of the deal I think the Pirates have a reasonable shot at getting that.

Diamondbacks got 33 games from Marte, Caleb Smith, Humberto Mejia and Julio Frias.

Its not unreasonable to think Peguero will be more valuable than that combination.


That’s really not how trades work. It’s value lost vs value received.

At the time of the trade Marte had 2 years of control left and amassed 6.6 fWAR during his final 2 years of control. If Peguero is worth more than 6.6 fWAR during his time with the Pirates, it’s a win.


They traded Marte with 2 years left.
As long as Peguero exceeds the fWAR Marte gained in years that the Pirates would’ve had control that’s a win, right?


Just me but I always hated this silly exercise because I think it understated how valuable 4+ WAR players are and how much they can impact a team.

That being said, I would agree if Peguero has 2 season in which he accumulates over 6.6 WAR the trade is a win.

However if Peguero gives up 6 years of 1.2 WAR a year for 7.2 WAR in total I would not consider that a win.


I knew this wasn’t going to be objective, but it was worse than I thought. The apology tour continue…no wonder nothing changes…failure is accepted


not sure what this post shows more…..the amount of prospects that bust…or the spotty trade record of cherington

bit of both i suppose


I think if we looked at every team, the failure rate is pretty high on the side that trades proven mlb players for prospects. “Can’t miss” prospects fail a lot……or take years to actually meet expectations.


Agree it’s a bit of both. The failure rate is pretty high, though, which is why he grabbed several middle infielders and catchers. You hope you get lucky with one of them like we did with Endy.


took a quick look at the 40 man. its currently at 39 but will be at 40 once Cruz is healthy.

the rest of the 60 man IL is… Brubaker, VV (will be gone), Jarlin Garcia (will be gone), Kranick, Tucupita.

So if they want to keep Brubaker Kranick and Tucupita, theyre already gonna have to be dropping dudes.

And there’s less and less dudes who youd think they wanna drop. Andre Jackson i guess?

and thats before factoring in any guys to ADD to the 40 to avoid R5, any signings, etc.

I think it’s gonna be a pretty crazy offseason.


The bullpen isn’t exactly filled with must-keeps. Borucki and Jackson are excess. I’m not sure Kranick survives after basically 2 years of not pitching. There’s all that fringe at the end of the pen with de los Santos, Perdomo, Bolton and Yohan – they won’t keep all four, particularly if they sign a reliever or two.

Middle infield could use some thinning out. Capra’s a free guy. I wouldn’t give up on Bae yet, but it is harder to find space for him now that Gonzales is up.

In the OF Palacios is probably still just filler, a 5th OF playing 4th OF on a second division team.

That’s maybe 6 guys without having to make a really hard choice. You get emotionally attached to certain dudes, but in the end they’re 35s and 40s, and there are so many more of those on the market every day.


right. i know IM not really emotionally attached to anyone from this crew you mention, but it’s more about assuming that THEY are attached to them


You’re not wrong there.You could waste hours tracking Cherington’s fetishes for certain guys who remained on the roster far too long.


I think we have a roster crunch of mediocrity. I feel like Bae is perfect example. Worth being on a 26 man roster, but doesn’t really make sense with our best 26. Trading him to the Athletics for major league talent 0-1 war production for league minimum feels right, receiving a few 18 year olds or relievers in return.


overall the returns just feel so mid. just feels liek a total teardown shouldve returned just one more blue chip guy, but i dunno.


What total tear down? All of these players except Castro were going to be gone at the end of this year regardless. Getting anything in return for them has to be a positive and at least a couple of the new guys have a chance to be contributors in the near future and the other two teenagers might or might not become real players down the line.


I’m talking about the entire body of work going back to 2019.


The article covers Ben’s entire trade history with the Pirates and I agree with jaygray that the results have been pretty meh. The so-so returns have allowed the Reds to surge past us in their rebuild.


Their return is meh because the Pirates always trade for quantity instead of quality


The reds had the best draft this year in my opinion. There farm is loaded. We have an edge in pitching but they got a lot stronger with there first 2 picks. Still would take Skenes over their first 4 pitchers drafted and I really like Lowder and Floyd.


i guess the padres deals have tended to go at least relatively well.

bednar, endy (altho he was from the mets), Suwi is okay-enough for a few man-years of Musgrove and Frazier.

maybe we can imagine that endy was temporarily a Padre, as opposed to Lucchesi being temporarily a Pirate, in order to keep the “Padres deal go well” vibes going.

Lets go, Jackson Wolf and company!


After reading the breakdown of all these trades, count me as not impressed.


It always amazes me what I refer to as “The Love Song of the Yinzer Pirates fan” every August 1. The team is usually 10-30 games under .500 and not even close to contention, so they move a few of the guys who put them in that position and its like “They always trade away their good players!” I like to point out that the 2020 team in the shortened season did not even win 40% of their games, and who was on that team? Josh Bell, Jameson Taillon, Jacob Stallings, Joe Musgrove etc…..When all is said and done I like the talent that has been assembled in the last three years.


No one likes analyzing trades more than me. What a great read. Thans again Tim!

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