Today at 6:00 PM EST is the MLB trade deadline.
The Pirates have already made probably their biggest move in dealing Jose Quintana and Chris Stratton last night. They also traded Daniel Vogelbach for Colin Holderman. I’d expect more moves today before the deadline passes.
As we wait for the moves to be finalized, I wanted to take a look back at the trades made under Ben Cherington in the two years leading up to this season. It’s still early for results, but we have an idea of where some of the earlier deals are now heading.
Starling Marte for Liover Peguero and Brennan Malone
This was the first deal under Ben Cherington, made before the 2020 season and before the pandemic shut things down. Marte had two years remaining on his contract, and his value was lower at the time than it was after the 2021 season, when he signed a four year, $78 million deal. Cherington was dealing with a common problem where Pirates players were essentially worth less than their names. Arizona traded for Marte because of his potential to be better than what he had been with the Pirates leading up to the trade. They were hoping that the real Starling Marte would show up, and he did in 2021.
The Pirates had too many players who were underperforming in Pittsburgh, only to go elsewhere and get back on track. Cherington went more for upside in these trade returns, as seen here. Peguero and Malone were both in short-season ball at the time of this deal. Peguero has the highest upside, ranking as one of the best prospects in the system. He’s in Double-A during his age 21 season. His stats haven’t shown the upside, and he will need to gain consistency in applying his tools on the field to reach and stick in the majors. Malone has dealt with injuries and control issues, limiting him to only 5.2 innings above the Complex League.
The jury is still out on this deal, and it mostly relies on Peguero living up to his potential. Without that, this looks like a very bad return for one of the best players the Pirates had.
Joel Cesar for Austin Davis
The first year was quiet for the Pirates, with the minor addition of Austin Davis being a highlight of the 2020 deadline. COVID played a big role in altering that season, and we know that the Pirates got busy blowing up their roster after the season. I’m not highlighting every minor move, but this one led to a positive chain in additions.
Josh Bell for Eddy Yean and Wil Crowe
Josh Bell was a replacement level player in 2020. He was worth 2.9 fWAR in 2019 and 1.3 in 2018. Since this deal, he’s been worth 1.9 and 2.5 WAR the last two seasons with the Nationals. The Pirates traded Bell when his value was low. They received Wil Crowe for immediate help, and Eddy Yean for long-term help.
Crowe has emerged as a bullpen option who can pitch leverage innings. Yean is a big pitcher who has had control issues, and is getting hit a lot in Greensboro’s bullpen this year — both home and away. At best, this deal could give the Pirates a pair of relievers, but it looks like Bell for a set-up man at best.
Like the Marte deal, the Pirates were selling low on a player with two years of control remaining.
The Joe Musgrove Trade
A month after trading Bell, the Pirates moved Joe Musgrove in a three-team deal. They received David Bednar, Hudson Head, Drake Fellows, and Omar Cruz from the Padres. They also added Joey Lucchesi, before flipping the left-handed pitcher to the Mets for Endy Rodriguez, which really sealed this deal.
Bednar has provided the immediate return here as an All-Star closer. The Pirates could probably deal him at this point and get a similar return as the Musgrove trade — perhaps better. Endy Rodriguez leads the way for the rest of the group as one of the top ten prospects in the system. He’s currently hitting the ball well in Greensboro. Fellows has been limited to 11.2 innings by an injury. Cruz has a reliever profile, but is currently injured in Double-A. Head has raw power, but a long swing with holes gives him a three-outcomes approach in High-A at the age of 21.
This isn’t a bad deal so far. Musgrove has been outstanding, looking exactly like he did in 2018-2019. He has since signed a five year, $100 million extension. The Pirates traded him with two years of control remaining. Bednar is making this deal right now, and if Endy Rodriguez works out, this will easily look like one of the best moves for Cherington.
The Jameson Taillon Trade
The Taillon trade was made just after the Musgrove deal, with the Pirates getting Roansy Contreras to highlight the move. Contreras was a good scouting find as a lower level guy who advanced during the pandemic. He has since emerged as one of the top long-term pitching options for the Pirates’ rebuild. That’s what you want when you’re trading a previous long-term pitching option for a previous Pirates’ rebuild. Contreras is still an unknown, so this deal isn’t quite a win.
The Pirates also got Canaan Smith-Njigba, Miguel Yajure, and Maikol Escotto. The rest of this deal has taken a hit. CSN made the majors this year, but is currently out with an injury. He still factors into the outfield mix with the current upper level group. Yajure has struggled in the majors and in Indianapolis. Escotto has a lot of raw power, but struggled at a young age in Greensboro and was sent down to Bradenton again.
Taillon was coming off Tommy John surgery, with two years of control remaining. His value was low, but there were reports that Gerrit Cole lobbied the Yankees to pay up for him. I don’t think they regret the deal right now. I don’t think the Pirates do, either, but they need Roansy Contreras to work out.
Shendrick Apostel for Duane Underwood Jr.
The Pirates got a middle reliever with control for a prospect who hasn’t played in 2022. This is very similar to the Austin Davis deal, where they got a Major League talent for a guy in the lower levels of their system who was almost out of the game. The Pirates have Underwood Jr. under control for three more seasons.
The Adam Frazier Trade
The Pirates went back to San Diego six months after the Musgrove trade, sending Adam Frazier for Jack Suwinski, Tucupita Marcano, and Mitchell Miliano.
Suwinski has been the biggest standout here, leading NL rookies in home runs before being sent down to the minors. He’s going to need to hit more than homers to stick in the majors, but has shown average starter upside. Marcano has received a few shots, and shows some potential to at least be a bench guy. Miliano has been getting hit hard in Greensboro, with no control.
The Pirates weren’t selling low here. Frazier had a 2.9 WAR at the time of the deal, up from an 0.8 in 2020. He had a 2.7 WAR in 2019. The Pirates sold other players at a low value with two years remaining. They opted to keep Frazier, let his value increase, and dealt him at the deadline with a little over a year of control remaining. Suwinski has been more valuable than Frazier this year, in less time. This deal is looking good, and might be an argument against what the Pirates did with Marte and Bell.
Clay Holmes for Diego Castillo and Hoy Park
This deal I don’t understand. Holmes wasn’t pitching well for the Pirates, but was cheap with multiple years of control remaining. He’s got two more after this season with the Yankees. He’s emerged as a lights out reliever, with a 1.77 ERA and a 2.59 xFIP this year. That change happened almost immediately last year, following the trade. It’s another sign of the challenge that Cherington had with some players who may have never succeeded in Pittsburgh. That said, it doesn’t add hope that the Pirates couldn’t do anything with Holmes in a season and a half, only for him to immediately flip a switch elsewhere.
Castillo and Park both look like bench options. Castillo could develop into a starter, which would make this deal make sense. Otherwise, it’s a lateral move at best, and a still-existing red flag for the MLB development in Pittsburgh.
Tyler Anderson for Carter Bins and Joaquin Tejada
The Pirates tried to deal Anderson to the Phillies, before that deal fell through. That deal involved a catcher and a right-handed pitcher. They made the same deal with Seattle, adding Carter Bins and Joaquin Tejada. Bins is a solid defensive catcher who hasn’t been hitting in Triple-A, but has shown some power, with a .197 ISO. Tejada has thrown 19.1 innings in the Complex League, with a lot of strikeouts and a low average, but poor control.
Anderson was a rental, and lower value, so getting any potential MLB help is solid. Bins could be a backup catcher with power, and Tejada is a wild card.
Richard Rodriguez for Bryse Wilson and Ricky DeVito
Rodriguez had a solid 2021 season, and the Pirates definitely traded him at his highest value. Bryse Wilson has pitched 55.2 innings in the majors this year, showing the potential to be a reliever and spot starter. Wilson is coming off a month of July with a solid 3.27 ERA in 22 innings. If he can maintain this going forward, his contribution alone will make this deal look like a win. DeVito is a 23-year-old pitcher working in relief in Greensboro, with solid strikeout numbers and control issues.
Braeden Ogle for Abrahan Gutierrez
The Pirates tried to add Gutierrez in the first Tyler Anderson deal. They went back and got him by flipping minor league left-hander Braeden Ogle. Gutierrez boosts the catching depth, while Ogle has seen some improvements in Triple-A, but not enough yet to reach the majors.
Austin Davis for Michael Chavis
Remember that deal during a slow 2020 deadline? By this point, Joel Cesar wasn’t playing baseball. The Pirates flipped Austin Davis for Michael Chavis. This deal isn’t a monster. Chavis is replacement level and a platoon option. He is under control for three more seasons, and can provide power off the bench. Everything here is a bonus, as Davis and Chavis were essentially free players. These small moves don’t move the needle much, but they can find cheap talent to complement a team.
The Jacob Stallings Trade
The Pirates definitely didn’t sell low on Stallings. They traded the veteran catcher at a high point, getting MLB starter Zach Thompson, and minor leaguers Kyle Nicolas and Connor Scott. Thompson has back of the rotation potential. I think Nicolas could have a higher upside, either as a middle of the rotation starter or a leverage reliever. Scott has been inconsistent at the plate in Altoona this year. Stallings has struggled in Miami, with his offense cratering.
This deal is a perfect way to summarize the entire trade history of Cherington. The odds of a standout, impact player are slim. The odds of an average starter are higher. The odds of a 40-45+ player who will only serve as a complement to a contending team are more likely. It will all come down to the development.
It’s still very early for Cherington’s deals. That said, the Pirates traded Starling Marte, Josh Bell, Joe Musgrove, Jameson Taillon, Clay Holmes, Adam Frazier, and Jacob Stallings. Most of them had multiple years of control. That’s the start of a contending team. The downside the Pirates had was they didn’t have enough time to contend with these players, with some coming off down years, and some possibly never succeeding in Pittsburgh.
I’m not sure that the Pirates got equal long-term value in return. Which of the players above will make an impact on the next contender?
Peguero could be an impact player. So could Rodriguez. Contreras as an impact starter. Bednar in the bullpen.
As for average starters, Jack Suwinski leads the group right now, though no one has added comfort. There are some role players in guys like Wil Crowe and potential role players that will emerge from the group of Castillo, Marcano, and other 40-45+ grade players.
As long as there are question marks surrounding Peguero, Rodriguez, Contreras, and Suwinski, the Pirates will be working from behind on these deals. They have the potential to finish ahead, but will need to show that they can finalize the development of these players moving forward.