The Pirates could be sellers or buyers at the deadline. But why should we trust Ben Cherington?

The 2024 Pittsburgh Pirates have sent fans on a rollercoaster of emotion, to say the least. Look no further than this past weekend.

As things stand in this writing, the Pirates are 43–47 and sit four games behind the San Diego Padres for the final National League Wild Card spot. Word on the streets is the Pirates might be buyers. With a 4–6 record in their previous 10 games, they might be sellers.

But why should we trust Ben Cherington either way? Let’s just take a look at the trades he’s made since he was hired after the 2019 season. He’s made a lot of them.

In January 2020, he shipped longtime outfielder Starling Marte to the Arizona Diamondbacks in exchange for SS Liover Peguero and RHP Brennan Malone.

Marte hasn’t exactly been a superstar since he was traded, but still, he’s amassed a 10.3 fWAR in four-plus seasons, including a 2021 year where he stole 47 bases and hit .310 with a 132 OPS+ for two teams.

Peguero, who has spent all of 2024 to this point with Triple-A Indianapolis, has a 0.2 fWAR and hit .239 with a 78 OPS+ in 201 at-bats in 2023. He’s essentially been passed up by the likes of Jared Triolo and Alika Williams.

I won’t even get into Malone, who is 23 and hasn’t surpassed Single-A Bradenton and has only thrown 35.2 innings his entire minor league career. He’s probably not going to contribute for the Pirates, so that trade was a swing-and-a-miss.

In December 2020, he sent first basemen Josh Bell to the Washington Nationals in exchange for RHPs Wil Crowe and Eddy Yean. Let me start by saying my biggest problem was *when* they moved Bell, who had a 142 OPS+ in 2019 but just an 82 OPS+ in 2020.

Bell, like Marte, hasn’t been a superstar since he left, sporting just a 4 fWAR in four-plus seasons. Again, though, I want to stress that my problem was when he was moved.

The Pirates tried Crowe as a starter in 2021, where he threw 116.2 innings and amassed a 5.48 ERA. They moved him to a reliever, where he had a 4.38 ERA in 2022 and was DFA’d after throwing just 9.2 innings in 2023. He finished with a -0.6 fWAR with the Pirates and hasn’t thrown in the major leagues since.

Yean, who is 23 in Double-A Altoona, has actually thrown 45 innings with a 3.20 ERA in 2024. Still, the odds probably aren’t very high he ends up contributing with the Pirates at some point.

I wouldn’t call this trade a disaster, but it’s still definitely not a “W.”

The next month, he shipped off Joe Musgrove in a three-team trade that sent Musgrove to the Padres and yielded a five-player return that included C/OF Endy Rodriguez, RHPs David Bednar and Drake Fellows, LHP Omar Cruz and OF Hudson Head.

First, let’s get into what the Pirates got in the haul before going into what Musgrove’s done in San Diego.

The trade gave the Pirates Bednar, a two-time All-Star closer who led the National League in saves in 2023 with 39. He’s currently on the injured list but was pitching better after an awful start.

The next one is Rodriguez, who in my opinion, is the wild card of this trade and will play a huge role in whether or not it turns out to be a successful one or not.

He burst onto the scene in 2022, hitting .323 with 25 home runs across three minor league levels. He made his MLB debut in 2023, but only hit .220 with a 67 OPS+ in 186 at-bats to pair with a 0.6 fWAR. He’ll likely miss all of 2024 recovering from Tommy John surgery, so 2025 will be a massive year for him.

Cruz isn’t even in the Pirates organization anymore and is 25 in Double-A. Head is 23 and has only moved up one minor league level since 2021. He’s hitting .222 with a .746 OPS in High-A Greensboro this year.

Fellows is 26 and currently in Triple-A Indianapolis. It’s not impossible the Pirates see him at some point, especially with all the injuries to their pitching staff. He has a 4.42 ERA in 55 innings this year and a career 4.81 ERA in the minors.

Musgrove has been a staple in the Padres rotation, even throwing a no-hitter in 2021. He has an 8.7 fWAR in four-plus seasons. So far, this trade is up in the air — truly hinging on what Rodriguez ends up being.

January 2021 was a busy month for the Pirates. After dealing Musgrove, Cherington made what really seemed like a good trade for a while, when he sent Jameson Taillon to the New York Yankees in exchange for SS Maikol Escotto, OF Canaan Smith-Njigba and RHPs Roansy Contreras and Miguel Yajure.

Taillon missed the 2020 season while he recovered from Tommy John surgery. He threw 37.1 innings in 2019 with a 4.10 ERA and 0.8 fWAR.

The trade, at first, seemed like a W, because of the emergence of Contreras, who threw 95 innings in 2022 and had a 0.9 fWAR. Unfortunately, he faltered in 2023, having a 6.59 ERA in 68.1 innings and then a 4.04 ERA out of the bullpen in 2024 before he was sent to the Los Angeles Angels for cash. He had a 0 fWAR in ’23 and ’24.

Still, though, the Pirates got FOUR players for him. Surely one of them panned out, right? Well, let’s take a look at the other three.

Yajure threw 39.1 innings for the Pirates in 2021 and 2022, where he had an 8.69 ERA and a -0.8 fWAR. Yikes.

OK, what about CSN? The 25-year-old brother of Seahawks wide receiver Jaxon had a -0.5 fWAR and 37 OPS+ in 37 at-bats with the Bucs between 2022 and 2023. He was DFA’d multiple times but is spending 2024 with Triple-A Indianapolis.

Escotto, who is still only 22, is hitting just .197 with High-A Greensboro and is unlikely to contribute to the Pirates.

Again, Taillon isn’t exactly a superstar, but he’s earned a 7.1 fWAR the past four-plus seasons. That’s way more than anything the Pirates got for him. He’s got a 2.99 ERA and 1.3 fWAR in 81.1 innings in 2024 while pitching for the division-rival Cubs, who are in last place.

They made a couple other trades in 2021 — shipping off Adam Frazier for Jack Suwinski and sending Richard Rodriguez to Atlanta for Bryse Wilson. Neither of those trades are fleeces or “L’s” in my opinion, though if Suwinski can find his 2023 form, that Frazier deal looks like a W.

Then, in November 2021, the team sent Jacob Stallings to Miami in exchange for RHPs Zach Thompson and Kyle Nicolas and OF Connor Scott.

Scott is a career .240 hitter with a .669 OPS in the minor leagues and is now a part of the Milwaukee Brewers organization. Thompson had some flashes, I suppose, which led to some people on Twitter (cough, cough, Rum Bunter, cough) proclaiming he was good.

He was not. He had a 0.2 fWAR in 2022 in 121.2 innings, pitching to a 5.18 ERA.

Nicolas has been solid in 2024, pitching to a 4.00 ERA in 27 innings with a 0.3 fWAR. He’s been much sharper lately and has become one of the more reliable guys in the bullpen. He relieved Aroldis Chapman on Sunday in the 9th inning of a one-run game and induced an inning-ending groundout with the bases loaded.

Stallings, who won a Gold Glove the season before he was shipped off, has been . . . less than impressive. He had a combined -0.5 fWAR in 2022 and 2023 in Miami, though, to his credit, has a 0.8 fWAR and is slugging .429 this season with basement-dwelling Colorado.

This trade, in my opinion, is another “up in the air” type of deals. Stallings would certainly be a better option behind the dish than almost anybody we’ve had since he left, but if Nicolas turns out to be a high-leverage guy or a closer, it’s hard to complain about that return.

The next big move was in August 2022, when he sent rental Jose Quintana and Chris Stratton to the Cardinals for RHP Johan Oviedo and 1B/3B Malcom Nunez.

Odds are, they weren’t re-signing Quintana, and Oviedo showed tons of flashes in 2023. He’s recovering from Tommy John in 2024, but if he comes back strong and healthy, he figures to be a back-end rotation guy. I lean more towards that trade being a W.

In my opinion, two of his better trades came when he shipped Kevin Newman to Cincinnati for RHP Dauri Moreta and Daniel Vogelbach to New York for RHP Colin Holderman.

Moreta, who is recovering from Tommy John in 2024 (seems to be a common theme) had some ups and downs in 2023, but generally was solid as a high-leverage guy, pitching to a 3.72 ERA and 2.93 FIP in 58 innings.

Holderman has also been very good, and in my opinion deserved some All-Star votes (sans his past week or so).

So, to recap, Cherington has dealt away guys like Starling Marte, Joe Musgrove, Jameson Taillon, Josh Bell, Kevin Newman, Adam Frazier and Jacob Stallings.

That return has netted, what I think are right now, three good major leaguers. Holderman, Bednar and Moreta. Other guys like Rodriguez and Nicolas are more on the fence. I’ll also give him credit for acquiring Connor Joe, a solid major league utility guy.

I yap about all this to say, Cherington doesn’t have a home run trade like acquiring Bryan Reynolds for three months of Andrew McCutchen like the previous regime did (not saying Huntington is some all-world general manager, don’t get it twisted.)

Cherington’s done some nice work (drafting Paul Skenes & Jared Jones to name a couple). But, when you think about it, only acquiring one guy via trade that you can say is a solid MLB position player (Joe) in year five of a rebuild where you gave up as much as you did, is Cherington really the guy to trust when it’s time to buy or sell?