Pittsburgh Pirates: Ranking Ben Cherington's Trade Deadlines

Ben Cherington has now been the Pittsburgh Pirates general manager for four trade deadlines. But how do they compare to one another?

The trade deadline is now far in the rearview mirror, and the Pittsburgh Pirates are now in the dog days of summer, like every Major League ballclub. This marked general manager Ben Cherington’s 4th trade deadline with the Bucs. Although the Pirates didn’t sell off a ton of players, they did get back some noteworthy prospects this season.

We’ll get into that later, but I want to go back and rank each of Cherington’s trade deadlines as Pirate GM. We will go from worst to best, though I am excluding the 2020 deadline. The first reason is because of the shortened season, so it’s not entirely fair to judge the Pirates’ decisions at that time. The second is because the Pirates didn’t do much, only trading Jarrod Dyson for international bonus pool money (which turned into Po-Yu Chen).

While the Pirates really haven't traded away anything major in any of their trade deadlines, and they've received back at least one good prospect or productive player, let's now take a look at Cherington's "worst" trade deadline as the Pirate GM.

2021

The 2021 trade deadline was sort of a turning point in the rebuild. They traded off what was really the remaining parts of their core from the late-2010s. On top of that, they were still able to get some value out of the low-cost/low-profile moves they made at the time. This is by far the most active deadline the Pirates have had during Cherington’s reign.

The big trade from the Pirates’ 2021 deadline was sending infielder Adam Frazier to the San Diego Padres for three prospects. Frazier was in the midst of a career year, as he was hitting .324/.388/.448 with a 127 wRC+ at the time of the deal. Frazier also displayed good defense at second base, as well as left field. However, given he only had one more year of control left and there were some concerns about the sustainability of his season, the Pirates deal Frazier to the Padres.

The headliner was Tucupita Marcano, who at the time had skipped High-A, Double-A, and Triple-A before making his Major League debut. Marcano was generally considered a top-15 prospect in the Padres’ system at the time. Keep in mind this was before they traded C.J. Abrams. Mackenzie Gore, James Wood, Robert Hassell, or saw Ha-Seong Kim graduate prospect status.

The second piece of the Pirate return was Jack Suwinski, a power hitting outfielder in the midst of a breakout season. There was some concern about his swing and miss, though he showed off the potential to hit 25+ home runs annually with a lot of walks, as well as above-average speed and defense. The third player involved in the package was relief prospect Michell Miliano, who was more or less just a low-risk throw-in.

This trade has ended up in favor of the Bucs. Frazier struggled with the Padres and was eventually dumped to the Seattle Mariners for two players who weren’t considered top 30 prospects by most sources. Suwinski has been the most productive player in this deal, as he’s breaking out in 2023.

He’s been streaky, but he’s already hit 21 home runs on the season while providing value on the base paths, and a decent glove out in center field. Marcano’s season was cut short because of an ACL injury. However, he’s still only 23, and could still end up as a solid utility man.

The second major deal the Pirates made was sending closing pitcher Richard Rodriguez to the Atlanta Braves. Rodriguez was also in the midst of a career season, as he pitched to a 2.82 ERA, 2.60 FIP, and 0.83 WHIP, primarily working as the Bucs’ 9th inning man. There were some worrying signs, like a poor 22.8% strikeout rate, a 0.47 HR/9 despite being one of the worst pitchers in limiting hard contact and having a fly ball rate over 50% (57.5%), and a suspicious and major drop in fastball spin rate once MLB started to crack down on foreign substances on the mound. 

Regardless of the concerns, the Pirates were still able to deal him to the Braves for two players. One was Bryse Wilson, a former consensus top 100 prospect who at that point had yet to really be given a chance to show what he could to in the Major Leagues. Up to that point of his career, Wilson only had 76.1 Major League innings under his belt that spanned four seasons. The second player was Ricky DeVito, an 8th round draftee who had shown off some impressive stuff, but lagged significantly behind in the command department.

Rodriguez was a disappointment for the Braves, as they likely viewed him as a potential cog in a competitive bullpen. Meanwhile, neither Wilson nor DeVito did much for the Pirates. The trade has since ended as a wash for both sides. Rodriguez was non-tendered the following offseason, Wilson struggled in his one season in Pittsburgh, then was traded to the division rival Milwaukee Brewers, and the Pirates then traded DeVito for utility man Mark Mathias, who is no longer in the organization.

This trade has really ended as a wash for both the Pirates and the Braves. Rodriguez, while he posted a solid ERA for Atlanta, also gave up six home runs in just 26 innings. Rodriguez struggled so badly in September that he was left off Atlanta’s Postseason rosters. At the end of the season, Atlanta non-tendered Rodriguez. Wilson was given the reins to a rotation spot in 2022, but struggled greatly with an ERA+ of just 75. He was traded to the Milwaukee Brewers this past off-season where he’s found a niche as a solid long relief/low-leverage arm. DeVito only spent one year with the Pirates as well, again showing some promising offerings but greatly struggling with command. He was then traded to the Texas Rangers this past winter for utility man Mark Mathias. DeVito has missed most of 2023, pitching just 22 innings.

The third noteworthy move the Pirates made was trading Tyler Anderson to the Seattle Mariners. The Pirates had signed Anderson the prior off-season to be a back-of-the-rotation innings eater, and that’s exactly what the lefty provided. In 18 starts, Anderson worked to a 4.35 ERA, 4.27 FIP, and 1.20 WHIP. He only struck out 20% of opponents and had a mediocre 1.39 HR/9 rate, however, he walked just 5.8% of batters faced. These are average to slightly below average numbers, but Anderson did what he was asked to do: go at least five innings in every start and keep the Pirates in the game most of the time. Only three of his starts saw him allow 4+ earned runs.

The Pirates originally were going to send Anderson to Philadelphia, but a trade fell through at the last minute, which prompted the Bucs to turn to the Mariners. The Pirates received two players in return. Joaquin Tejada was one of the Mariners’ most recent international signees. So far, he’s shown a decent ability to strikeout batters but has given up walks at a below-average rate.

Carter Bins was an 8th round catcher with some pop. Bins had a solid second half to 2022, but has missed most of the 2023 season and has just 30 plate appearances thus far. Anderson meanwhile continued to post slightly below-average results but gave the Mariners some more innings.

The last and final trade of note was relatively small, and that was sending lefty relief prospect Braeden Ogle to the Philadelphia Phillies for catcher Abrahan Gutierrez. Ogle struggled for the Phillies’ minor league affiliates, prompting them to release him after 2022. He then resigned with the Pirates last off-season. Gutierrez is a good fielding catcher with a solid hit tool. He was looking good at Greensboro but has since struggled at Altoona this season.

Suwinski is hard carrying this deadline. All the players in the Rodriguez trade are no longer with the respective teams involved in his original trade. The jury is still out on Marcano, Tejada and Gutierrez, however. I think Marcano still can prove to be a useful utility man, and Tejada is still so young it would be unfair to completely give up on him. Gutierrez has struggled at Altoona this season. I also doubt the Pirates view Carter Bins anything more than organizational depth at this point as well.

2023

The Pirates’ most recent trade deadline might be the second-best of Cherington’s tenure. The Pirates only traded rental players. No player they moved is controlled beyond this season, meaning if the Pirates wanted to, they could bring back every player they traded during the upcoming off-season. Though moving rental players means you’re not going to see very many high-profile prospects get moved either.

The first move the Pirates made was trading veteran first baseman Carlos Santana to the Milwaukee Brewers. Santana was signed to a one-year deal to help fill the void at first base. Santana provided the Pirates with about league average hitting numbers, slashing .235/.321/.412 with a .319 wOBA, and 99 wRC+. Santana displayed his trademark plate discipline, only striking out 17.6% of the time with a healthy 11.5% walk rate. He also gave the Bucs some pop at first base with a .177 ISO. 

But a lot of Santana’s value came with his glove. Santana might go down as the Pirates’ best defensive first baseman behind Kevin Young. In just 721.1 innings, Santana racked up +6 defensive runs saved and +2 outs above average. That’s very impressive defense, especially for a first baseman, which helped make up for his league average bat. Santana will be a finalist for the NL first base Gold Glove.

The Pirates only got one player in return for Santana, and that was infielder Jhonny Severino. A former international signee, Severino is still pretty young as he’s only in his age-18 season. Severino projects to hit for a lot of power and has a high offensive ceiling. But his position long term is still up for debate. Although he’s a shortstop now, he’s already an average runner, and by the time he fills out, could move to left field or third base. Severino draws comparisons to former Minnesota Twins’ slugger Miguel Sano.

The second trade the Pirates made involved two players. That was Rich Hill and Ji-Man Choi. Hill is the oldest player in the league at 43 years young. Like the soft-tossing lefties before him, Hill was brought in as a veteran innings eater, and he did just that. Only three of his 22 outings lasted fewer than five innings. All told, Hill pitched 119 innings, working to a 4.76 ERA, 4.41 FIP, and 1.48 WHIP. Granted, those numbers are a tad inflated by a few bad outings, like his Opening Day start, which accounts for 11.1% of his total earned runs allowed.

Choi was brought in to serve as a platoon mate for Santana over at first base. The longtime Tampa Bay Rays 1B was traded to the Bucs last off-season in exchange for Jack Hartman. Unfortunately, Choi’s tenure in Pittsburgh did not go as planned. Choi hit the injured list in just the second week of the season and didn’t return until the second week of July. However, Choi hit well in this short stretch in July, batting .268/.295/.634 with a 140 wRC+, and four homers in 44 plate appearances.

Choi and Hill were both sent to the San Diego Padres for a package of three players. One already made his Major League debut, and that was Jackson Wolf. A former 4th-round pick, Wolf is a soft-tossing lefty with a side-arm delivery. In the 88.1 innings pitched prior to the trade, Wolf had a solid 4.08 ERA, 1.09 WHIP, and 3.88 FIP.

Wolf has already made one start for the Pirates’ Double-A affiliate, pitching 4.2 innings, allowing just one earned run, striking out five, and allowing zero walks. Wolf has a four-pitch mix, including a four-seamer, slider, curveball, and change-up. He also has good command.

The Pirates also received another teenage prospect in Estuar Suero. Like Severino, Suero was also an international signee. The switch-hitting outfielder has some major power/speed projection. He stands at 6’5”, 185 pounds, giving him a very projectable frame. He’s also a plus runner, so he could end up in center field long-term. He’s one of the Pirates’ youngest top prospects at just 17 (won’t turn 18 until the end of this month).

The final player included in the deal was Alfonso Rivas. Although Rivas was more or less a throw-in to help the Pirates with their now lack of first base depth, he’s done pretty well since coming to Pittsburgh. He has seven hits, including two home runs, two walks, and seven strikeouts in 28 plate appearances.

It’s a little too early to tell how this deadline will work out for the Pirates in the long haul. Two of the three prospects they acquired are younger than 18. Though Wolf could potentially contribute to the team as soon as September. He’s already made his big league debut. Plus both Suero and Severino have a high ceiling, even if there is some risk between the two. Rivas may have been just a throw-in, but he has done well in his first few plate appearances for the Bucs. The Pirates went with the high-upside play here but also got back some players who could help right now.