Colin Holderman

The Pirates are off to an excellent start to begin the 2023 season, currently sporting a record of 16-7 with a run differential of +25. It’s too early to simply assume that they are quite this good, especially since many of their games have come against teams that aren’t expected to be competitive, like the Reds and the Rockies. But after a couple of 100-loss seasons and an even worse winning percentage in the shortened 2020 season, it’s an encouraging development, even if it’s not wholly sustainable.

As with any rebuilding club, the talent on the roster has been acquired in various ways. Some were brought into the organization with high draft picks, like Ke’Bryan Hayes and Mitch Keller. There are former amateur free agents, like Rodolfo Castro and Ji Hwan Bae. There’s also some veterans on modest free agent deals, like Carlos Santana, Rich Hill and Vince Velasquez. But a sizable portion of the roster was acquired via trade, as is often the case with rebuilding clubs, who use the playbook of sending established players away for prospects.

Some of these trades have been on the minor side, bringing in role players like Connor Joe or Mark Mathias. There have also been a few trades that haven’t worked out, such as the Clay Holmes deal, but here are some that have had a significant impact on the current roster. Also, just as a quick side note before launching into this, general manager Neal Huntington was fired in October of 2019. While most of the moves listed below were completed by his successor, Ben Cherington, the credit on the first few goes to the previous regime.

• July 31, 2017: Dodgers acquire Tony Watson for Oneil Cruz and Angel German.

Watson had spent his entire career with the Pirates up until this point, having been drafted by them and making it to the majors by 2011. He had posted consistently solid results, never finishing a season with his ERA above 4.00, even coming in below 2.00 in both 2014 and 2015. In the 2017 season, he was in his final campaign of control before becoming a free agent. The Pirates made the playoffs in three straight years from 2013 to 2015 but fell below .500 in the two subsequent seasons. That made it a fairly logical move to flip an impending free agent reliever who wasn’t going to be a qualifying offer candidate.

German was a relief prospect who never amounted to much, topping out at Double-A in 2019. He reached free agency and signed a minor league deal with the Rays in 2020 but was released before pitching for them. But landing Cruz is in this deal looks like it will work out quite well for the Bucs. He’s currently on the 60-day injured list due to an ankle injury that required surgery, but he could be back around August. There are concerns about his strikeout rates and shortstop defense, but he has some of the best tools in the league, consistently featuring among the leaders in terms of exit velocities, arm strength and sprint speed. His eventual value will be determined by how much he refines the rougher edges in his game, but he clearly has incredible talent and should impact the club in some way. He’s not slated for free agency until after the 2028 campaign.

• January 13, 2018: Astros acquire Gerrit Cole for Joe Musgrove, Michael Feliz, Colin Moran and Jason Martin

After two straight disappointing seasons, the Pirates clearly decided to lean in to their rebuild prior to 2018, making two significant trades within a few days of each other. The first one saw them deal Cole, who had two years of control remaining, to Houston. In return, they got four younger players, the most significant of whom was Musgrove. At the time of the trade, there were some questions about whether he was better suited to be a starter or a reliever. The Bucs gave him the chance to prove himself as a capable rotation member, which worked out for both parties. He posted a 4.23 ERA in 325 1/3 innings over three seasons in Pittsburgh, showing enough potential to establish his bona fides as a starter. That gave him enough trade value to get flipped to his hometown Padres, allowing the Pirates to add more young talent, which we will get to below.

• January 15, 2018: Giants acquire Andrew McCutchen and cash for Kyle Crick, Bryan Reynolds and international bonus pool space.

As if the Cole trade wasn’t enough of a sign that the rebuild was on, the Pirates took down the Jolly Roger and waved a white flag when they traded McCutchen just two days later. He had been an iconic player for the franchise for many years, helping them return to contention after two decades of losing, earning the 2013 National League Most Valuable Player award in the process. He had signed an extension with the club going into 2012, a deal that ran through 2017 with a club option for 2018. He had fallen off from his MVP heights but the $14.5MM option price was still a bargain, so the Pirates made the easy decision to pick that up instead of paying the $1MM buyout. However, he would eventually play that season in San Francisco.

While the trade of a face-of-the-franchise player like McCutchen was undoubtedly frustrating for the fan base, it’s paying off now. Crick had some decent results at times for the Pirates but was ultimately released in 2021. The real coup of the deal is Reynolds, who has emerged as a new face-of-the-franchise player for Pittsburgh. He’s hit 79 home runs in his career and is currently sitting on a batting line of .282/.359/.484. He’s set for free agency after 2025, which has made him the constant subject of rumors, both the trade and extension variety. To date, both paths are still open, making it unclear if Reynolds will be part of the next playoff club in Pittsburgh or an extra bullet added to the bottom of this list.

• January 27, 2020: Diamondbacks acquire Starling Marte and cash for Liover Peguero, Brennan Malone and international spending money.

The Pirates managed to sneak above .500 in 2018 but had a dismal season after that, going 69-93 in 2019, making it unsurprising that the selloff continued. Marte had previously signed an extension with the Bucs that ran through 2019 but had two affordable option years, meaning he still had a couple of years of control at the time of this trade. But with contention in that time frame seeming unlikely, he was sent to the desert.

Malone is now 22 years old and has yet to climb higher than Class-A in the minors. Injuries and the pandemic have limited him to fewer than 30 professional innings. Peguero in on the 40-man roster and made his MLB debut last year, though he got into just a single game. His prospect rank has faded in recent years, but he was still considered to be among the 10 best in the system as of the start of this season. He’s off to a slow start this year in a small sample of 11 Double-A games, so he’ll have to turn things around to stop his stock from falling further.

• January 19, 2021: In a three-team trade, the Padres acquire Joe Musgrove and the Mets acquire Joey Lucchesi while the Pirates receive David Bednar, Endy Rodriguez, Hudson Head, Drake Fellows and Omar Cruz.

As mentioned earlier, Musgrove had established himself as a viable starter, enough to reap a pile of prospects that has already worked out well for the Bucs. Bednar has become one of the better relievers in the game, currently sporting a 2.82 ERA and 31.3% strikeout rate while racking up 30 saves. The fact that he happens to be a Pittsburgh kid is just icing on the cake. He’s yet to reach arbitration and isn’t slated for free agency until the 2026-27 offseason.

There’s still plenty of time for the Bucs to get even more out of this deal as well, as the other four players are still in their system. The most notable of them is Rodríguez, who is on the 40-man roster but hasn’t made it to the majors just yet. The catcher/infielder/outfielder is a versatile player with a potent bat, making him one of the most highly-touted prospects in the sport. He’s considered to be one of the top 50 prospects in the league by each of Baseball America, FanGraphs, Kiley McDaniel of ESPN, Keith Law of The Athletic and MLB Pipeline.

• January 24, 2021: Yankees acquire Jameson Taillon for Roansy Contreras, Miguel Yajure, Maikol Escotto and Canaan Smith-Njigba.

Taillon had some good seasons working in the Pittsburgh rotation from 2016 to 2018, but Tommy John surgery wiped out most of his 2019 and all of his 2020. He was set to return to the mound in 2021 when he still had a couple of years of control remaining. Despite the injury uncertainty, the Yankees believed in Taillon enough to acquire those two seasons, sending four prospects to Pittsburgh in exchange.

Yajure is already gone from the organization and Escotto’s prospect stock has fallen off, but the other two players are still on the roster. Most evaluators project Smith-Njigba for a bench/utility role, though he’s still young, turning 24 this coming weekend. Regardless, the most significant player in this batch seems to be Contreras, as he’s already in the club’s rotation. He has a 3.84 ERA through his first 119 2/3 innings in the big leagues and isn’t slated for free agency until after 2028. If he can continue to hold his own against major league hitters, then the Pirates have a rotation building block in place for the foreseeable future.

• July 26, 2021: Padres acquire Adam Frazier for Jack Suwinski, Tucupita Marcano and Michell Miliano.

Frazier was drafted by the Pirates and had spent his entire career with them up until this point, establishing himself as a solid utility option. His bat was roughly around league average, a useful asset for a player who could be plugged in at almost any position on the diamond. He was having a BABIP-backed spike in 2021, hitting .324/.388/.448 when the Pirates sold high, trading him away while he still had a year and a half of control remaining, getting three young players in return.

Miliano is a 23-year-old reliever who’s yet to surpass High-A, so he’s probably the least likely of this group to be a key contributor going forward. Marcano is in the big leagues but is expected to serve a bench/utility role. Suwinski, however, has the chance to be an impactful member of the club. He’s been playing all three outfield spots in the big leagues, seeming to be a passable defender at any of them. He’s also hit 24 home runs in just 122 games thus far. His 30.3% strikeout rate is certainly on the high side, but he’s also drawn walks at a healthy 12% clip. His .209/.310/.440 career batting line to this point in his career translated into a 109 wRC+, and his batted-ball data in 2023’s small sample is particularly interesting (95.2 mph average exit velocity, 56.3% hard-hit rate). He’s not slated for free agency until after the 2028 season.

• July 22, 2022: Mets acquire Daniel Vogelbach for Colin Holderman.

Vogelbach was a known power threat, having hit 30 home runs with the Mariners in 2019, but he struggled in the next few seasons and bounced to the Blue Jays and Brewers, getting non-tendered by the latter club after the 2021 season. The Pirates signed him to a modest deal worth $1MM plus incentives, watched him get into a groove and flipped him to the Mets after a few months.

Holderman has just 35 major league appearances to this point in his career, but the results are fairly encouraging.  He has a 3.20 ERA with a 49.1% ground ball rate, helping him keep the ball in the park to such a degree that he’s yet to allow a home run. That surely won’t be able to last forever, but he’s working himself into a high-leverage role with the club, having accrued eight holds already in this young season.

• August 1, 2022: Cardinals acquire José Quintana and Chris Stratton for Johan Oviedo and Malcom Nuñez.

Quintana has a long track record of success in the majors but struggled in both 2020 and 2021, getting bumped to the bullpen in both seasons. The Pirates bought low by signing him to a one-year, $2MM deal and giving him a shot to re-establish himself as a starter. It worked, as he registered a 3.50 ERA with the Bucs, allowing them to flip him to the Cardinals for a couple of younger players. Nunez has yet to reach the majors and is struggling in Triple-A right now, but he’s still just 22 years old. Baseball America and FanGraphs both considered him the club’s #21 prospect coming into the season.

Oviedo was initially a starter with the Cards but got bumped to the bullpen last year. The Pirates are giving him another shot at rotation work with good results so far. He has a 2.78 ERA in 11 starts for Pittsburgh between last year and this year, with a 22.4% strikeout rate, 10.1% walk rate and 54.8% ground ball rate. Oviedo has more than doubled his curveball usage in 2023, and is throwing the pitch harder than ever before. It’s a small sample, but his swinging-strike rate is up from 11.2% to 14.6%. He’s under club control through 2027.

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It’s no secret that the Pirates are a low-spending club. Looking at data from Cot’s Baseball Contracts, which goes back to the year 2000, they’ve never even made it to the middle of the pack in terms of payroll. They’ve frequently been at the very bottom of spenders and their highest relative rank was getting to 19th place way back in 2001. For the clubs that keep the purse strings that tight, it’s essential that they succeed in getting the most out of younger players who haven’t yet maximized their earning power.

Since the major league economic system artificially deflates player salaries until they get to six years of service time, it’s important for a club on the stingy side to find good young players, whether it’s those that they draft/sign or those they get from other organizations. As the Pirates appear to be on the verge of being respectable again, or perhaps have already arrived, they seem to be doing just that. As mentioned, they’ve had the occasional clunker, like the Holmes deal, but a decent chunk of the roster was built via trade. Two of their regular outfielders were acquired in trades, as was their everyday shortstop, although he’s on the shelf right now. Their dealing has also given them two of their five rotation members, some of their best relievers, a few utility players and some key prospects.