Ben Cherington has been the General Manager of the Pittsburgh Pirates for nearly five years.
The five years under Cherington have been highlighted by a tanking period where they tore down the Major League roster, followed by a slow progression toward contending for the long-term. If the 2024 trade deadline is a sign, we’re now in the era of the Pirates pushing toward contending status.
There were plenty of trades that took place during the last five years, and if you look closely, you can see that the Pirates have gone through some eras under Cherington.
It’s difficult to provide an objective evaluation of any individual trade, or even a group of trades. Rather than focus on trade grades, I’m going to be focusing on those different eras of this rebuild, with the Pirates hopefully moving into a time where they can compete, evermore.
THE FIRST ERA: FOLKLORE
Back when the Pirates were still changing for the better, wanting was enough. Pirates fans lived each year for the hope of it all, but August always slipped away like a bottle of wine.
The idea of trading all of your established players for prospects who can help in the future can sound like folklore.
Under Neal Huntington, the Pirates did the same thing during the first five years. Those trades did land players who would help the team contend in 2013-15. Their rebuilding trades at the time led to Josh Harrison, Charlie Morton, Jeff Locke, Joel Hanrahan (later traded for Mark Melancon), Jeff Karstens, and Jose Tabata. They also landed a few players who had success elsewhere, like Brandon Moss and Hunter Strickland.
The 2013-15 teams weren’t built on those rebuilding trades, but those winning teams were supported by the returns.
The first two years under Cherington saw the Pirates take a similar rebuilding approach, as they traded away all of their established players for the potential of future help.
Cherington was gathering stones, never knowing what they’ll mean. Some were thrown, and some could make a diamond ring.
Below are the trades made during this tear-down era of Cherington’s rebuild with the Pirates.
STARLING MARTE
The Return: INF Liover Peguero, RHP Brennan Malone
The Timing: Marte was dealt almost immediately into Cherington’s time as the GM, getting moved on January 27, 2020, right as a pandemic was starting to sweep the globe. The Pirates had options for the 2020 and 2021 seasons on Marte, and he was coming off a 3.6 WAR season.
Current Status: Peguero is currently in Triple-A, batting .254/.314/.403. He’s fallen on the depth charts for second base, which is his most likely path to the big leagues. He’s in his age-23 season this year, and his first full year in Triple-A. Malone has been limited by injuries, and pitched most of this season in the FCL, with a lot of control problems in his age-23 season.
Chance to Improve: There’s a chance that Malone could stay healthy and figure out his control, but that’s looking unlikely at this point. He’s pitched 27.2 innings since the trade, and stalled this year in the rookie leagues. Peguero could turn things around in Triple-A, with the chance to be a future starter in the majors. This might not happen with the Pirates, as they have several options ahead of him right now, and into the 2025 season. Peguero’s future value to the team could come as a trade chip for a team hoping to benefit from a change of scenery.
Outlook: Marte was the biggest trade chip the Pirates had, and it’s unlikely that this deal will result in anything significant for a future Pirates winner. Peguero is still young enough that he could turn things around, but you’d hope for a better return by this point for a 3-4 WAR outfielder with two years of control remaining.
JOSH BELL
The Return: RHP Wil Crowe, RHP Eddy Yean
The Timing: Cherington didn’t make another trade until after the 2020 season, and after the MLB Winter Meetings. Bell was traded on Christmas Eve 2020, coming off the worst season of his career, with two years of control remaining.
Current Status: Crowe is currently pitching in Korea, after the Pirates let him go last summer. Yean has taken a step forward this year in his jump to Altoona. The 23-year-old has a 3.17 ERA in 54 innings, while showing significant improvements to his control.
Chance to Improve: Yean is emerging as a guy who could be a future reliever in the majors, arriving in the next two years.
Outlook: The Pirates sold low on Bell, and the return was disappointing. There was a time when Crowe looked like he might have been a quality reliever in the bullpen, but that quickly faded. Yean could give the Pirates some value going forward. In hindsight, the Pirates would have been better off keeping Bell and hoping for a rebound in 2021, which he had for another team.
JOE MUSGROVE
The Return: RHP David Bednar, C Endy Rodriguez, LHP Omar Cruz, RHP Drake Fellows, OF Hudson Head
The Timing: Musgrove was traded at the end of January 2021, which really signified the tear-down era of the rebuild. He was coming off an improved season in the shortened 2020 campaign, and had two years of control remaining.
Current Status: Bednar is the Pirates closer, and has been one of the best relievers in the game since the trade. Rodriguez was added as a secondary part of the deal, with the Pirates acquiring LHP Joey Lucchesi from the Padres, and flipping him to the Mets for Endy, who will return next year as the likely starting catcher. Fellows has been injured for most of his time since the trade, but has a 3.95 ERA in 43.1 innings with Altoona this year, in his age-26 season. Head has stalled in High-A the past three seasons, and will be entering his age-24 season next year. Cruz was lost to the Padres in the minor league phase of the 2023 Rule 5 draft. He’s since made improvements to his control and strikeout totals, reaching Triple-A this year.
Chance to Improve: This deal is all about Bednar and Endy right now. There’s a chance the Pirates could get relief depth from Fellows. Bednar also will be a free agent following the 2026 season, so the long-term impact from him might come from a future trade. Rodriguez could be the starting catcher beginning next year, with a chance to be an above-average player.
Outlook: This is one of the best deals Cherington made during the tear-down era. Musgrove continued his 2020 breakout, but the Pirates got two players who can help them during their contending years. Getting a starting catcher and a closer from one trade is the goal of these types of deals.
JAMESON TAILLON
The Return: RHP Roansy Contreras, RHP Miguel Yajure, OF Canaan Smith-Njigba, INF Maikol Escotto
The Timing: Taillon was traded less than a week after Musgrove. He was set to return from his second Tommy John surgery, and had two years of control remaining.
Current Status: The Pirates cut ties with Contreras earlier this season. He’s since shown improvements with the Angels, but nothing that would make him more than a middle reliever. Yajure is out of baseball this year, after the Pirates cut ties with him following the 2022 season. They also cut ties with Smith-Njigba this year, and he’s yet to catch on with a new team. Escotto is in his third season in High-A, batting .208/.257/.382 in his age-22 season.
Chance to Improve: Unless Escotto massively turns things around, the Pirates will get nothing from the Taillon trade in their contending years.
Outlook: This deal is looking like a bust. The Pirates could have held onto Taillon to see how he returned from Tommy John. He eventually made a good return, which shouldn’t be a surprise for anyone who knows Taillon’s work ethic and drive to get better. It’s unlikely that the Pirates get anything significant from this deal, outside of hope in 2022-23 that Contreras could have been part of the long-term rotation.
ADAM FRAZIER
The Return: OF Jack Suwinski, INF Tucupita Marcano, RHP Michell Miliano
The Timing: Frazier was traded at the deadline in 2021, in the middle of the best season of his career. He had two years of control remaining, and hasn’t repeated the success from that season.
Current Status: Marcano was banned from the game for betting on baseball last season. Miliano was released after last season, and is out of the game. Suwinski hit 45 homers between 2022-23, but has taken a step back this year, and is currently in Triple-A.
Chance to Improve: If the Pirates can turn Suwinski around, they could have an average outfielder capable of playing all three spots. He’s in his age-25 season right now, and can be optioned to the minors in 2025 to serve as depth until he figures it out. The Pirates just added Bryan De La Cruz at the 2024 deadline, so the opportunities for Suwinski will likely come as a depth piece.
Outlook: The Pirates sold high on Frazier, showing the benefits of keeping a guy around to watch his value rise. The return of Suwinski could help a future winner. He’s only a year removed from an above-average season in the majors, and could be a valuable part of the future contending years.
JACOB STALLINGS
The Return: RHP Zach Thompson, RHP Kyle Nicolas, OF Connor Scott
The Timing: Stallings was coming off the best season of his career in 2021, putting up a 3.1 WAR and winning the NL Gold Glove behind the plate. The Pirates traded him following the 2021 season. He had three years of control remaining, and has yet to repeat that performance over the last three years.
Current Status: Thompson and Scott are both out of the organization. Nicolas is in the Major League bullpen, and has been one of the best relievers on the team over the last month and a half.
Chance to Improve: Nicolas has a lot of upside as a potential closer, and is starting to settle in at the Major League level. He’s in his age-25 season, and will have six more years of control following this year.
Outlook: Once again, the Pirates sold high on a player who didn’t repeat his value at the time of the deal. Nicolas has the chance to be a late-inning reliever for a contending team, and seems to be settling into that role in 2024.
CLAY HOLMES
The Return: INF Diego Castillo, INF Hoy Park
The Timing: Holmes was traded at the 2021 deadline, after struggling in his move to the bullpen. He had 3+ years of control remaining. The Yankees adjusted his pitch usage, and he’s been one of the best relievers in the game over the last three years.
Current Status: Castillo and Park were used as MLB depth, and were both traded. Castillo brought back Scott Randall, who has been a depth option in A-ball. Park brought back Inmer Lobo, who is a soft-tossing lefty having success in Single-A, but without a lot of positive projectability in the upper levels.
Chance to Improve: It’s very unlikely that Randall or Lobo make the majors.
Outlook: This deal has been a bust, but it may have revealed some flaws that the Pirates could learn from in future years. There was no reason to trade Holmes at that point, especially for two players who profiled as bench depth. The adjustments Holmes made after the trade were to simplify his arsenal and use his best pitches, which is something the Pirates could have done. He dropped his curveball, settling on a simple approach of a sinker and slider. He then added a slower variation of the slider with a sweeper, which has been a plus offering. To their credit, the Pirates have since seemed more comfortable with some pitchers taking a simplified approach, while working to develop more pitches in the majors.
RICHARD RODRIGUEZ
The Return: RHP Ricky DeVito, RHP Bryse Wilson
The Timing: Rodriguez was dealt at the 2021 deadline, and his career collapsed after the move. He had a few years of control remaining.
Current Status: DeVito was traded for 2023 bench infielder Mark Mathias. The Pirates traded Wilson for cash ahead of the 2023 season, after he struggled in the rotation. He’s since found success in the Milwaukee Bullpen, with replacement-level performances.
Chance to Improve: This deal is done, unless they invested the cash from Wilson into Gamestop as a long-term hold.
Outlook: The Pirates sold high on a set-up man, and sold low on their best chance of a return from this deal. If they had kept Wilson, he’d be another middle relief option on a good pitching staff. This deal was pretty insignificant compared to others of this era, and won’t have any long-term impact.
KEVIN NEWMAN
The Return: RHP Dauri Moreta
The Timing: Newman was traded following the 2022 season, after a 1.2 WAR season. It was the best year he had since 2019, and the infielder had two years of control remaining.
Current Status: Moreta is out for the 2024 season with Tommy John, but was looking like one of the more promising relievers the Pirates had before the injury.
Chance to Improve: With four years of control remaining, Moreta could emerge as a late-inning reliever, or at the least, a reliable middle relief option. He’ll be returning next year during his age-29 season.
Outlook: With so many middle infield options pushing Newman, the Pirates traded an expensive player when his value was high, getting a controllable reliever with upside. I think Moreta could play an impact in the bullpen during future contending years, which will make this deal stand out.
BRAEDEN OGLE
The Return: C Abrahan Gutierrez
The Timing: The Pirates were trying to get Gutierrez at the 2021 deadline in another trade. When that fell through, due to an injury to a second player in the deal, they sent Ogle for Gutierrez straight-up.
Current Status: Gutierrez is in Double-A for his age-24 season. He’s batting .233/.270/.318 and has seen his power drop this year.
Chance to Improve: Gutierrez has the defense and power potential to be a depth option behind the plate, but will need to make it past Double-A first.
Outlook: This is a very minor deal, but I do like the potential of Gutierrez to eventually become a depth option out of Triple-A. That will be valuable in one of the inevitable years where the Pirates get crushed by inevitable injuries behind the plate.
THE TEAR-DOWN ERA
The Pirates currently have David Bednar as their closer. Endy Rodriguez looks like the best catching option going forward. Kyle Nicolas and Dauri Moreta could be impact relievers on a contending bullpen. Jack Suwinski could turn things around and get back to above-average play in the outfield. They also have some potential depth options in Liover Peguero, Eddy Yean, and Drake Fellows, with Peguero having the biggest chance of breaking out and providing an impact to a future contender.
This isn’t the type of return you’d hope for from a rebuild that sent away two years each of Starling Marte, Joe Musgrove, and Jameson Taillon, while also selling high on Adam Frazier and Jacob Stallings. Selling low on Clay Holmes really highlighted that the Pirates didn’t know the potential value of the players they inherited. That also raises the question of whether they knew the potential value of the players they acquired.
Without the side deal with the Mets for Endy Rodriguez, this batch of trades would look like a disaster, with the Pirates essentially using all of their tear-down trades to build a future bullpen. Marte, Bell, Musgrove, Taillon, and Holmes combined for 26.3 WAR during their remaining years of control. That should have resulted in close to $235 million in trade value. That amount should have landed the equivalent of two elite prospects, along with a top 100 guy, with a good chance for one future impact starter emerging from the group. All of those eggs are in the Endy Rodriguez basket at this point.
THE SECOND ERA: SPEAK NOW
The Pirates have long been experts at sorry and keeping lines blurry. And all the fans they’ve run dry have tired lifeless eyes, because they burned them out. Every offseason, the Pirates would paint a blue sky, and every trade deadline they’d go back and turn it to rain. Fans lived in the chess game, wondering which version they’d get on the phone each night.
Following what was a disappointing tear-down era, the Pirates started creating their own value for the future.
They would add rentals in the offseason with a chance to rebound, only to flip those players at the deadline. This was mixed with giving opportunities to a lot of the players in the tear-down era trades, while also giving opportunities to players who shouldn’t have been given so much big league time. Josh VanMeter is the Joe Alwyn to the Tortured Poets Department known as Pirates fans.
The tear-down era and the creating-value era have some overlap. By the 2022 season, the Pirates were pushing more toward an era where they were starting to actually adding big league talent, after three offseasons of inaction. Their focus still remained on the future by every trade deadline.
Years from now, we might look back at this era and regret ignoring when some fans said “run as fast as you can”. There’s also the chance that this creating-value era helped to boost a disappointing tear-down era. The goal of this era from 2022-23 was largely still about creating future value.
TYLER ANDERSON
The Return: C Carter Bins, RHP Joaquin Tejada
The Timing: Anderson was a rental for the 2021 season. The Pirates seemed set on finding a catcher, first trying to deal him for Abrahan Gutierrez. They eventually dealt him to Seattle for Bins and Tejada.
Current Status: Tejada had a good season in the FCL bullpen last year, but is out for the year this year after 4.2 innings in the lower levels. Bins is in his fourth year at the Double-A level, batting .207/.331/.387.
Chance to Improve: Bins has the defense and power potential to be a backup in the majors, or at least a depth option. He’s been used as upper-level depth this year, and could find it difficult to crack Triple-A with Jason Delay on the roster.
Outlook: This deal won’t amount to much, outside of potential catching depth. The Pirates were heavily investing in catching during the 2021 season. They made two trades at the deadline for future depth pieces, while drafting Henry Davis first overall. This was a few months after acquiring Endy Rodriguez. The Anderson trade gives them a boost in minor league depth for the future.
DANIEL VOGELBACH
The Return: RHP Colin Holderman
The Timing: Vogelbach was a one-year rental, and was dealt at the 2022 deadline.
Current Status: Holderman has emerged as a late-inning relief option this year, mixing in with Bednar and Aroldis Chapman in the 7th-9th innings. He’s struggled as of late, but is having the best season of his career, with a spike in strikeouts.
Chance to Improve: The Pirates have Holderman for another four seasons of control following this year. He will likely factor into the bullpen mix for at least the 2025-2026 seasons, if not longer.
Outlook: This has been a good deal. The Pirates have excelled under Cherington at trading for pitching, and acquiring sleeper relievers. Holderman can join Nicolas, Moreta, and Bednar from the tear-down era to give the Pirates an elite bullpen in the future contending years.
JOSE QUINTANA/CHRIS STRATTON
The Return: RHP Johan Oviedo, INF Malcom Nunez
The Timing: Quintana was a rental in 2022, and was paired with Stratton to bring back a promising return in Oviedo and Nunez.
Current Status: Oviedo is currently out with Tommy John, but looked like one of the best starters on the team during the 2023 season. The rotation has improved since then, but Oviedo looked good enough that he could have a spot when he returns. Nunez has spent most of the last two seasons in Triple-A, and is hitting .267/.330/.406 with ten homers this year.
Chance to Improve: Oviedo has three years of control remaining, and should be in the Pirates rotation mix in 2025 for his age-27 season. Nunez could emerge as a depth option. He’s only in his age-23 season, and has taken a step forward in a few key metrics this year, with a reduction in strikeouts, and slight increases in walks and power.
Outlook: This was the best trade of this era. Getting Oviedo could provide the Pirates with a long-term starter for their contending years. He’s not going to be a top starter, but he could be a reliable back-of-the-rotation option, similar to Jeff Locke/Charlie Morton under Huntington’s rebuild. Nunez also has the chance to be a depth option, or develop into a candidate for first base. The deal was made possible by the Pirates signing a good reclamation project in Quintana.
NICK GARCIA
The Return: UTIL Connor Joe
The Timing: The Pirates added Joe ahead of the 2023 season, trading away 2020 over-slot third rounder Nick Garcia.
Current Status: Joe has been a great addition to the bench over the last two years, putting up a combined 2.1 WAR. He’ll have three years of control remaining following the 2024 season.
Chance to Improve: Joe gives the Pirates a contending-level bench option, capable of playing infield and outfield. He’s entering his age-32 season, so the hope would be that he maintains the current production. He could also eventually bring someone back in a trade.
Outlook: This has been a great low-key deal. Joe has been one of the better performers on a bad offense the last two seasons. He’s 32 and still growing up, and the Pirates can use him in a bench role for a few more seasons beyond 2024. Garcia was taken in the first draft under Cherington, and is currently looking like a potential middle relief depth option in the San Francisco system, after being taken in the minor league portion of the 2023 Rule 5 draft. The Pirates used the early potential of a future prospect to get a reliable bench piece as they started to shift toward a contending era.
ROBERT STEPHENSON
The Return: INF Alika Williams
The Timing: The Pirates added Stephenson as a waiver claim in late 2022. They traded him in 2023, after 14 innings in the bullpen and a 5.14 ERA. He adjusted his pitch usage and instantly became one of the best relievers in the game following the trade, in a situation very similar to the Clay Holmes trade.
Current Status: Williams improved his hitting in Triple-A after joining the Pirates, but has yet to bring that up to the majors. Stephenson netted a three-year, $33 million deal over the offseason, but went down this year with Tommy John.
Chance to Improve: If Williams can figure out how to carry his hitting over to the majors, he could at least be a bench option with plus defense at shortstop. He should be a depth option out of Triple-A in 2025.
Outlook: Like the Holmes trade, the Pirates weren’t able to get the best out of a reliever who instantly found success elsewhere. That might not have been good for Stephenson, as his move to a cutter-heavy approach may have precluded his injury. This deal is pretty insignificant, as Stephenson didn’t have value until he left. Williams might be a depth piece only, or he could emerge as a future middle infield bench option on a contender.
CARLOS SANTANA
The Return: INF Jhonny Severino
The Timing: Santana was a rental at first base in 2023, and was traded at the deadline.
Current Status: Severino is in his age-19 season, and just finished hitting .291/.373/.545 with ten homers and 12 steals in the FCL. He has since moved up to Single-A for the remainder of the year, and should be in A-ball next season.
Chance to Improve: Severino has power/speed potential, with the chance to remain on the left side of the infield. He’s currently the number 22 prospect in the system, and could be a future starter in the big leagues.
Outlook: If this trade works out, it won’t be until 2027-28. Severino has shown promise in the low levels this season, and isn’t a bad long-term get for a first base rental with little value.
RICH HILL/JI-MAN CHOI
The Return: OF Estuar Suero, 1B Alfonso Rivas, LHP Jackson Wolf
The Timing: Hill and Choi were both added ahead of the 2023 season. Choi was actually acquired in a trade for RHP Jack Hartman, taken in the fourth round of the 2020 draft.
Current Status: Rivas was let go following the 2023 season. Wolf was traded back to the Padres this year for infielder Kervin Pichardo, who is batting .262/.315/.369 in Double-A during his age-22 season. This deal was always about Suero, who had a .625 OPS in the FCL during his age-18 season.
Chance to Improve: Suero is a 6′ 6″, 180 pound projectable outfielder with power/speed potential. He’s the number 27 prospect in the system on his potential alone, and could get another shot at the FCL next year at the age of 19. Pichardo looks more like an upper-level organizational depth option.
Outlook: Like the Santana trade, the Pirates added a few rentals, then flipped them for the chance to develop long-term value. If this deal works out, it won’t be until the end of this decade, and it all relies on the development of Suero.
AUSTIN HEDGES
The Return: International Money
The Timing: Hedges was a one-year rental, and was one of the worst offensive catchers in the league. The Pirates landed extra international money for their 2023-24 class.
Current Status: The Pirates signed five more international free agents following the Hedges trade: RHP Victor Trejo, RHP Daviel Castillo, RHP Jeremia Berroa, SS Jayden Kim, and RHP Emmanuel Chapman.
Chance to Improve: The most notable names on the above list right now are Jayden Kim, a shortstop out of Australia, and Emmanuel Chapman, a pitcher out of Cuba. They were also two of the final signings of the 2023-24 class, which means they liked used the Hedges money. The 18-year-old Kim is batting .259/.452/.296 in 74 plate appearances during his pro debut in the DSL. Chapman, a 25-year-old pitcher out of Cuba, has a 3.82 ERA in 35.1 innings with Altoona, along with a 32:14 K/BB. He was the last person to sign in last year’s class.
Outlook: Hedges had zero value, and it’s a bit of a stretch to attribute Chapman or Kim to this trade. Still, the Pirates turned a rental into long-term value, with Chapman having a chance to add to the relief depth over the next few years.
RODOLFO CASTRO
The Return: LHP Bailey Falter
The Timing: The Pirates traded Castro to the Phillies at the deadline in 2023, getting back Falter. Both players were set to finish the 2023 season with less than two years of service time, and neither had established themselves in the majors.
Current Status: Falter has stepped up in the Pirates’ rotation this year. He currently has a 3.95 ERA in 95.2 innings, with a 64:28 K/BB. Castro has been depth out of the Phillies Triple-A squad, but hasn’t been in the majors yet this year.
Chance to Improve: This trade is already looking like a win. Falter just needs to remain a Major League starter to keep the return going. With all the depth the Pirates have in the rotation, it’s possible they eventually flip Falter for a bigger long-term return.
Outlook: This has been one of the best trades of this era, due to Falter’s breakout this year. Credit to the Pirates for sticking with his potential, through some unimpressive MLB results. He could eventually be forced out of the rotation with all of the upper-level minor league talent they have, but the eventual return if he’s traded will be greater than Castro’s value.
JT BRUBAKER
The Return: INF Keiner Delgado
The Timing: Brubaker joined the Pirates’ rotation in 2020, but had Tommy John surgery heading into 2023. He was traded early in 2024 to the Yankees for Delgado, in a move that may have wrapped up the creating-value era.
Current Status: Brubaker has started his rehab with the Yankees, and has one more year of control beyond this season. Delgado is the number 23 prospect in the system, batting .227/.302/.371 in Single-A, with eight homers and 15 stolen bases in his age-20 season.
Chance to Improve: Delgado has potential from the middle infield, with power and speed. He’ll continue to develop in the Pirates’ system, giving them a chance for a future starter, or at least a bench option.
Outlook: Another trade where the potential for success in Pittsburgh is punted toward the end of the decade.
THE CREATING-VALUE ERA
You could argue that the Pirates had better results with their trades during this era, when they were adding rentals and flipping them at the deadline, versus the tear-down era where they had guys with years of control.
Johan Oviedo and Bailey Falter could open the 2025 season in the Pirates rotation, behind the trio of Skenes/Keller/Jones. Colin Holderman could help boost the late inning relief group. They also have a contender-level bench option in Connor Joe, and another potential option in Alika Williams.
Most of these trades created value for the end of the decade. Jhonny Severino, Estuar Suero, and Keiner Delgado are all top 30 prospects in the lower levels. The extra international money added a few lottery tickets to the system, currently led by Emmanuel Chapman in Double-A.
Overall, the Pirates did better in this era than their tear-down era. This could be due to an overhaul in the pro scouting department during the first two years under Cherington.
THE CURRENT ERA: 1989
Looking at it now, it all seems so simple. If you’re wondering whether the Pirates are out of the woods yet, the moves made in 2024 answers that question. The Pirates were built to fall apart and fall back together in the first four seasons under Ben Cherington. They’re now in the clear, with a focus on winning at the Major League level.
The trades made since the end of the 2023 season have mostly been about winning now, and in the near-future. They’ve all been relatively minor, with a few mid-level trades at the 2024 deadline. The Pirates have yet to make a big splash in free agency, or add an impact player at the deadline. They are shifting away from the rentals of the creating-value era, and adding potential reclamation guys who could have value for more than one season.
That’s how it works. That’s how you get the girl.
This is a similar approach to the one they took around the 1989 season, when they traded for Jay Bell and Don Slaught to provide a boost for their 1990-92 contending years. Perhaps some of these contending-era trades will work out just as well.
DEIVIS NADAL
The Return: OF Edward Olivares
The Timing: In December 2023, the Pirates traded lower level outfielder Deivis Nadal to get Olivares for their MLB squad.
Current Status: Nadal was a lower level organizational guy, and has remained in that role in High-A. There was hope that Olivares could maintain the power surge he showed with Kansas City at the end of 2023. He didn’t do that, batting .224/.291/.333, before being sent to Triple-A.
Chance to Improve: Olivares could be used as depth out of Triple-A for the remainder of the year, but he’ll be out of options next year. He is also arbitration eligible, so chances are he gets non-tendered in the offseason.
Outlook: The Pirates took a low-risk chance to get a power bat with a few years of control. That hasn’t worked, and it’s unlikely that Olivares remains in the organization beyond this season.
AUSTIN STRICKLAND
The Return: C Joey Bart
The Timing: Early in the 2024 season, the Pirates sent 2023 8th rounder Austin Strickland to the Giants for former second overall pick Joey Bart. The 27-year-old Bart had four years of service remaining, but was replacement level with the Giants across parts of four seasons.
Current Status: Bart has emerged as the starting catcher in Pittsburgh this year, batting .271/.358/.496 in 148 plate appearances, with his power finally emerging.
Chance to Improve: The Pirates have Bart for three more seasons, and he’s looking like a guy who could factor into the catching mix for at least the 2025 season.
Outlook: This is another deal where the Pirates traded a player drafted under Cherington to get a potential long-term option. This deal has worked out very well so far, albeit in a small sample. For all of the catching that they acquired during the tear-down era, Bart is currently the best option they have. He could split time with Endy Rodriguez starting next season, creating the best catching group in years.
RODOLFO NOLASCO
The Return: RHP Daulton Jefferies
The Timing: The Pirates added Jefferies in a trade in early May 2024, sending Rodolfo Nolasco to San Francisco. Jefferies was added as a depth option, and has pitched ten innings for the Pirates.
Current Status: Jefferies is currently on the 60-day injured list with an elbow injury. He missed all of 2023 after Tommy John and a thoracic outlet injury. Nolasco has been putting up numbers in High-A similar to what he did last year in Single-A, which is a three-outcomes approach in the lower levels.
Chance to Improve: Jefferies showed some promise as a depth option, but his injuries continue to pile up, and it’s unlikely he factors into the future mix.
Outlook: Like the addition of Olivares, this was a low-key depth move, and it hasn’t worked out. The Pirates are set on relievers and relief depth, so there isn’t a big loss with this deal if Jefferies amounts to nothing.
2024 TRADE DEADLINE
The recent trade deadline continued the trend of the Pirates shifting into contending mode. Most of their trades were either to add Major League options, or to add depth for the Major League roster over the next few seasons.
They traded four of their top 50 prospects to get outfielder Bryan De La Cruz, infielder Isiah Kiner-Falefa, left-handed reliever Jalen Beeks. These were the first deals under Cherington where they really started trading from their prospect depth.
The Pirates dealt Quinn Priester to get infielder Nick Yorke. They also had a prospect swap with Baltimore, sending 2023 5th round RHP Patrick Reilly for 25-year-old Triple-A super utility player Billy Cook. Both moves traded from the pitching depth the Pirates have accumulated throughout their organization, while boosting their upper-level hitting depth.
Martin Perez was a rental this year, who was dealt for DSL left-hander Ronaldys Jimenez. It was a deal very similar to the Hill/Choi trade, also with the Padres. It also made up for the Pirates trading another DSL lefty for Triple-A left-handed reliever Josh Walker.
Outlook: You can read about all of the 2024 deadline deals in my post-deadline column, but this deadline shifted the Pirates fully into the contending era.
Williams: The Pirates Upgraded at the Trade Deadline, Without Using Money or Prospects
THE CONTENDING ERA
Let’s fast forward to three hundred takeout coffees later.
The Pirates have started to shift toward winning in the now during the 2024 season. The moves made could produce a few starters and key pieces for the contending hopes in 2025 and beyond.
Joey Bart may be finally realizing his upside as a former number two overall pick. Such a steal would be a great reversal of karma for the Pirates, who have long seen their prospects go on to have success elsewhere.
They’ll also hope for the same result from recently acquired Bryan De La Cruz. At the very least, Isiah Kiner-Falefa will provide another contending level bench option, or could be flipped in the offseason to reclaim some of the prospect value the Pirates lost at the deadline.
Nick Yorke and Billy Cook give the team two hitters who can help over the next few seasons. Both players are at least on the level of Liover Peguero, if not ahead of him on the depth charts. This further underscores the disappointing tear-down era.
We’ve yet to see the Pirates make a big splash as they shift to contenders. What is clear is that they’re no longer rebuilding, and are starting to look like a contender.
Based on the crowd reactions at PNC Park, this life is sweeter than fiction.
BEN CHERINGTON’S PITTSBURGH PIRATES TRADE HISTORY
Cherington inherited some good players during his rebuild, but didn’t get much long-term value from that group during his tear-down era.
He followed with his creating-value era, adding rentals and flipping them at the deadline. Those trades may end up being better than the cumulative returns from the Marte/Bell/Musgrove/Taillon/Holmes deals, despite the Pirates having less future value to trade away.
The first two eras left the Pirates with David Bednar, Endy Rodriguez, Colin Holderman, Kyle Nicolas, Dauri Moreta, Jack Suwinski, Johan Oviedo, Bailey Falter, Connor Joe, and a few depth options out of Triple-A. That’s a catcher, a good bullpen, two back-of-the-rotation starters, and a few bench options for a contender.
Cherington’s trade history hasn’t been great during the tear-down and rebuild years. It still has left some players who could be part of the next contender.
The current contending-era sees a shift in the approach. The Pirates are now on the other side of the trade process, dealing future potential for immediate value. We’ve yet to see them really go big in this approach, still targeting candidates who have yet to break out in the majors. The difference is if these players break out in Pittsburgh, they have options for a contending team in the next few years.
The 2024 Pirates often look like a mess. But they’re the mess that you wanted. This is a team looking like they’re on the verge of contending for years. And if the fans get burned, at least the pitching left them electrified.
