A rebuild is often defined by the drafts and trades the General Manager made leading up to the contending years. Year 5 has been proclaimed by those within the organization as the year the Pirates intend to be serious. So let’s revisit the trades that have led us to this point and assign grades based on the returns. Obviously, these grades can change with time as the players in these trades play more games and acquire more value, so this post may not age as well. I am not going to be analyzing every single trade, because quite frankly no one cares about the Michael Chavis for Austin Davis trade. It will be focused on the bigger moves that involve moving actual MLB players for prospects etc. We are not covering the 2023 trade deadline or the Marco Gonzales trade because we can’t truly judge them in a meaningful way.
Nationals Receive: Josh Bell
Pirates Receive: Wil Crowe and Eddy Yean

Do you want to know something depressing? As frustrating as Josh Bell‘s time was in Pittsburgh was, he’s arguably the best Pirates 1st Baseman in the 21st Century. He was one of the first victims of the rebuild and everyone, even at the beginning, was very underwhelmed by the return. The Nationals completely won this trade, enjoying a year and a half of Bell absolutely destroying the ball (138 OPS+ and 41 home runs) before being shipped off. Meanwhile, Wil Crowe was quite bad in his 3 seasons in Pittsburgh. Recently released by the organization in November, he put up an ERA of almost 6 as a starter in 2021 and ended as a mediocre-at-best reliever in ’22 and ’23. I would say something about Eddy Yean but he’s done nothing even worth mentioning. Grade: F
Diamondbacks Receive: Starling Marte
Pirates Receive: Liover Peguero, Brennan Malone, International Bonus Slot Money

It’s hard not to be a little biased here because Starling Marte is one of my favorite players to ever wear the uniform in my lifetime. Cherington shipped him out for 2 tools heavy prospects Liover Peguero and Brennan Malone. The return seemed light at first for a player like Marte, who had been consistently an upper echelon outfielder his entire career in Pittsburgh and he had control on an extremely team-friendly deal. The return looks even worse when you take into consideration the Marlins got Jesus Luzardo from the Oakland Athletics for half of a season. Malone might’ve been fun, but he’s pitched a grand total of 27 innings in pro baseball since coming over to Pittsburgh. Peggy still has some of the best raw tools in the system, but his continued issues with squaring up the ball with his swing and terrible approach at the plate make a successful MLB career unlikely. It is early in his career but considering Marte has gone on since this trade and put up 10.1 WAR it’s been pretty easy to consider this trade a loss. Grade: D
Padres Receive: Joe Musgrove
Pirates Receive: David Bednar, Endy Rodriguez, Omar Cruz, Hudson Head, and Drake Fellows
Mets Receive: Joey Lucchesi

Thank God the New York Mets desperately wanted Joey Lucceshi for who knows what reason because wow did it save this trade from being considered a war crime. Joe Musgrove has become an amazing pitcher for the Padres since departing for his hometown team following the 2020 season. The Pirates’ return has been much more of a mixed bag. I don’t feel like Omar Cruz and Drake Fellows are even worth mentioning, and Hudson Head has been a massive disappointment. David Bednar has been an excellent closer in Pittsburgh, you cannot deny it. Easily top 10 in the sport at what he does. In terms of a rebuild, however, how much value has he truly brought the Pirates? Terrible teams don’t need closers, the true test of his value will be tested this year as the Pirates attempt to compete. Endy’s rookie year was extremely whelming, especially with the bat. However, he’s a 70-grade defender and will be a reliable MLB player even if he never hits well. So while the value is lower and the Padres easily won the trade, getting 2 MLB players in a trade like this almost never happens. Grade: B-
Yankees Receive: Jameson Taillon
Pirates Receive: Roansy Contreras, Miguel Yajure, Canaan Smith-Njigba, Maikol Escotto

What used to be treated as the crown jewel trade of the BC era, this trade over the past year has not aged very well. What was seen as 2 pitching prospects in the top 100 and 2 intriguing minor league bats has turned into a deal where the Pirates might have gotten 0 MLB players. Roansy Contreras has been a massive disappointment, as he was seen as the guy to replace Taillon. Acquired as a flame-throwing righty, Contreras can now barely top 93 mph on his fastball. Miguel Yajure is now pitching in Japan after departing the organization in 2020, and the 2 hitting prospects the Pirates received have been middling as well. Canaan Smith-Njigba has struggled to establish himself as a major league player, and Maikol Escotto has put up a sub .700 OPS in the past 2 seasons. Taillon wasn’t anything special in New York, but losing this trade is something rebuilds can’t afford. Grade: D
Padres Receive: Adam Frazier
Pirates Receive: Jack Suwinski, Tucupita Marcano

This is the first truly slam dunk trade that we have discussed so far. After starting the All-Star game for Pittsburgh in 2021, the Padres traded for him to help in a playoff push. He subsequently put up a ghastly 64 OPS+ in his half-season in San Diego and was unceremoniously dealt to Seattle in that offseason. Tucupita Marcano never hit well enough to stay on the MLB team, was DFA’d this offseason, and was claimed back by San Diego. Jack Suwinski was the real prize, and while a controversial player you cannot deny acquiring an outfielder with solid defense and 30 home run power for a year of Adam Frazier is good business. Especially if what we saw from Suwinski in September is real. Grade: A-
Marlins Receive: Jacob Stallings
Pirates Receive: Zach Thompson, Kyle Nicolas, and Connor Scott

This is one of those trades where everyone loses. The Pirates dealt Jacob Stallings to the Marlins on the back of a 3 WAR season in 2021. Stallings has been downright terrible in Miami, struggling to post positive WAR most years, and was DFA’d this offseason. The goal was to acquire a pre-arb starter for the long-term rotation in Zach Thompson, who had a respectable rookie campaign in Miami. Thompson wouldn’t survive being in the rotation for a full season, however, and was shipped off to the bullpen because even the 2022 Pirates couldn’t stomach his performance. He was traded last offseason to the Blue Jays for Chavez Young, who is also not in the organization anymore. Connor Scott isn’t worth discussing, the only player who might be something is Kyle Nicolas. The rookie reliever struggled in his cup of coffee in the majors in 2023, but he has dynamite stuff and improvement on control should make him a staple bullpen piece. But ultimately this is a trade everyone lost. Grade: C
Yankees Receive: Clay Holmes
Pirates Receive: Hoy Park and Diego Castillo

I think it’s fair to say this didn’t work out. Clay Holmes struggled his entire time in Pittsburgh as a reliever, and we shipped him out at the 2021 trade deadline. Since then Holmes has become one of the best relievers in baseball for the Yankees, and he has assumed their closer role. Hoy Park and Diego Castillo both had stints with the major league team but never stuck due to poor play. Neither is with the organization anymore, Park is with the Athletics and Castillo is with the Diamondbacks. Luckily relievers are the easiest position to replace so it’s not a death blow, but it’s certainly not fun to think about. Grade: F
Mariners Receive: Tyler Anderson
Pirates Receive: Carter Bins and Joaquin Tejada

This is also somewhat of a nothing trade, as the Pirates were not going to extend Tyler Anderson but it would’ve been nice to see him finish the season as a Pirate during a career resurgence. Carter Bins is a career minor league catcher who will never be a major league player. He’s a guy you roster just so your real prospects can play baseball games. Tejada might be a bullpen guy. Maybe. Hard to say. He has alright numbers in the complex league, but he’s 20 and hasn’t even touched A ball. 2 players you’re probably never rostering. Grade: C-
Mets Receive: Daniel Vogelbach
Pirates Receive: Colin Holderman

Daniel Vogelbach was another player who saw a bit of a career resurgence in Pittsburgh, being a 118 wRC+ bat during his time here. Despite having an option for 2023 for about $1 million, the Pirates traded the DH for pre-arb reliever Colin Holderman. Vogelbach went on to continue to mash in 2022 for the Mets but struggled like the rest of the team in 2023. Holderman was barely a part of the team in ’22, but showed promise in the 2023 campaign. No one questions how good his stuff is but when Holderman misses his spot he gets crushed. Probably too inconsistent to be our 8th inning guy but he’s a solid bullpen piece for most teams. Grade: B-
Cardinals Receive: Jose Quintana and Chris Stratton
Pirates Receive: Johan Oviedo and Malcom Nunez

If you’re going to trade the best pitcher you’ve had in your entire tenure to the St. Louis Cardinals you better stick the landing. Jose Quintana was nails for the 2022 Pirates and at the deadline, Cherington shipped him off with Chris Stratton for Johan Oviedo and Malcom Nunez. I don’t think Nunez or Stratton are worth discussing. They’re both middling. Quintana started a playoff game and continued to deal for St. Louis down the stretch which earned him a 2 year deal with the Mets. The Pirates got Oviedo, who was a workhorse pitcher and a 2 WAR pitcher last season. He’s limited with his fastball but getting a good MLB starter with 5 years of control is worth a rental. Even with the Tommy John surgery he’s getting and missing out on the entire 2024 season. Grade: A-
Reds Receive: Kevin Newman
Pirates Receive: Dauri Moreta

This trade was a win just because I never have to watch Kevin Newman in a Pirates jersey ever again. It was just gravy that we also got a solid relief pitcher with the most aura of anyone in Major League Baseball. Dauri Moreta used this year to establish himself as a very reliable bullpen arm with his nasty slider. Newman was relegated to the bench for the Reds and DFA’d in September. Easy win in what seemed like a nothing trade but when it’s for relievers it’s hard to call it a slam dunk. Grade: B

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