Tier Ranking Every Ben Cherington Trade with the Pittsburgh Pirates

Tier Ranking Every Ben Cherington Trade with the Pittsburgh Pirates

MLB trade deadline is just a few short days away and the Pittsburgh Pirates find themselves in a very peculiar position. Will Ben Cherington be allowed to trade these major assets like Mitch Keller and David Benor with years left of control or will he only be tied to the rentals like IKF, Andrew Heeny, and Tommy Fam? In today’s video, Jim and I decided to take a look back at every single notable trade that Ben Cherington had made in his tenure and are going to try to decide if Ben Cherington is the guy to do this. The way we did this was making a tier list. Yes, these grades will be letters A all the way to F being they are trashes. And let me just say there’s a lot of ones that are down in that category. So, make sure to enjoy the video, leave a like on the video as well, subscribe to the channel. Let’s get into it. Okay, starting things off with our first trade degrade. It is Starling Mark Tay to the Diamondbacks for Leover Pigguero and Brennan Malone. Jim, I’ll start with you. What’s a what’s what are you ranking this? This is about as bad as it gets. Um, was it this was Ben’s first trade? It was Ben’s first trade. I mean, you look at what he gave up. Uh, Starling Marte since then has put up about 10 more. Uh, the players he got in return have not put up any war. So, I’m gonna grade this one just a straight up F. I mean, this was an awful trade. I mean, Starling Marte was coming off a 3.7 win season. He was he was Ben’s best trade chip that he inherited and he kicked off his tenure with a complete disaster of a trade. Yeah, I was leaning like D just because Pguero at least made the big leagues. But the problem is with him, every time he’s come up, he just sits on the bench and we can’t see a sample size. And where on earth is Brennan Malone at right now? Um, he’s just kind of disappeared. Um, if we want to settle on F, I’m fine with F. We want to do that. This is about as bad as it gets, especially when you consider the returns that Arizona got from Marte. the return that like I mean Marte was then traded multiple times after this and every time he was traded after this it was for a better return. Yeah, let’s settle on F there. Uh moving on. This was the Christmas Eve trade. Josh Bell to the Nationals for Will Crowe and Eddie Yeen. Josh Bell didn’t have very much trade value at this point. Um, but that also played into this like Ben traded him at his lowest possible value and then he immediately went on to put up back-to-back two plus war seasons when the Pirates could have used some first baseman. Uh, or traded him, you know, the year after. I’m also giving this one an F. I mean, this was this again like these were the these were the start of his this was the start of Ben’s tenure and both of these were disasters in my opinion. That’s fair. I I was going to go D as well, but after hearing your like discussion there, I am going to go with F as well, just because he did trade him at his lowest value. And it’s funny, Eddie Yeen seems to be finally getting some status to him. So maybe if he eventually shows up, we put this in D. Um, but yeah, we’re let’s settle on F. Moving on. This was a bigger return. Four players in return. Jame Tyion to the New York Yankees. One of many Yankees trades here today for for Rowanzi Contrarus, Michael Escodto, Kanan Smith and Jigba, and Miguel Yahuray. Love it. I’ll give him I mean, at least at least Rouanzi put up a positive war while he was here. Um, Tyon was coming off his second surgery. I’m gonna put this one at like a I I guess I’ll put this one at a C just because like Tyion was going into I think he had two more years left on his deal and and you weren’t really sure what was going to happen there. Uh and they did at least get something positive for him, but that was it. I mean C at best. I’ll I’ll I’ll cap it out at C. Um, Smith and Jigbuzz turned into a what if now I don’t he’s not even in the organization anymore. A lot of people wanted to see him. Rowani Contrarus, I remember the happy Rowanzi day on Twitter. Um, that died off really quick. Um, Escodto still in the system and Yahoo Ray’s long gone. Um, Tyion as well not on the Yankees anymore, so that kind of helps this, but I’ll cap it off at C. Moving on to a three-team deal with the Padres’s and Mets. This will probably be one of our only positive ones in today’s episode. The Pirates acquired multiple players being Andy Rodriguez, David Bednar, Hudson Head, Drake Fellows, and Omar Cruz. The Mets got Joey Lucessie, and the Padres’s get Joe Musgrove. What are we thinking about this one? Um, yeah. I mean, you you got what multi-time all-star David Bedar in return here. Uh, Andy Rodriguez, we still don’t really know exactly what he’s going to end up being. But you gave up a pretty good starting pitcher for that. I I’ll give this one, I guess, a C just because, you know, Bedar turned out to be really good, but like Musgrove, no one else has panned out from this trade. Uh, and Musgrove has been good ever since then. He’s been injured, but he’s been good. Didn’t Musgrove throw the first Padres’s no hitter that year, too? It was either the year that year or the year after. I think it was that year though. So, you’re going C. I might go B, like low B whenever we look at this tier list, just because they got a multi-time all-star reliever that maybe they can flip at the deadline. Um, uh, that would probably grade this weirder. I don’t know if we want to meet in the middle. I don’t know how we want to do this. So, I’m at a B. You’re at a C. What are we thinking? Um, I mean, if we want to go B, we can go B. I just it’s very close getting getting only a relief pitcher out of a starting pitcher with multiple years of control just uh doesn’t it doesn’t really move the needle for me I I love Benar great return like great guy great pitcher to have on your team but like you gave up seemingly seven war of Joe Musgrove for that see then I look at the one we just did though we gave Contraras a C. H. Let’s Maybe that one should be a D and this should be a C. This one’s better than this one’s better than that one. Let’s do that. Let’s put Tyion on and D and we’ll put this three team D on C. I like that. I I feel good with that. Um Adam Frasier to the Padres’s for the infamous Tuca Marano, Mitchell Milano, and good old Jack Sowinski. What do we think? Uh um I’ll give this one another B just because like Frasier, they they he traded Frasier at his peak value. He never really was what he was at that time of the trade after that. And they did get something out of Jack Sinsky. So like I think you got to at least acknowledge, hey, 2023 Jack Sinsky provided 2.6 6 war gave them 26 homers. Uh I’ll give this I’ll give this a B. I mean, Adam Frasier for for that doesn’t really seem that bad. That’s fair. I mean, you got like like you said, they got like a 26 home run season out of Jack Sinsky. We probably sadly won’t see that ever again. And then the other guy they got is banned for life now. And Tukita Marano and I like to call him Touque. Yeah, Touque. Um and then um Adam Frasier did end up coming back to the Pirates. So, I guess it full circle. I’ll go B as well. Uh, moving on. This one sucks. Klay Holmes to the Yankees for Hoy Park and Diego Castillo. I will say Diego Castillo’s walkup song was awesome. Literally had his name in it, but like I’ll just say this is like I’m going F. This is an F. I mean, Klay Holmes made multiple All-Star games after this trade and the Pirates Yeah. got nothing. Got nothing. I will I will say Klay Holmes as a pirate at times was frustrating, but just looking at what he’s become makes it even more frustrating. Um especially since he’s making starting pitcher money now at the New York Mets. Jacob Stallings to the Marlins for Zack Thompson, Kyle Nicholas, and Connor Sto. Kyle Nicholas is the only guy, well him and Thompson you could say, but you could say it was basically Kyle Nicholas became the best guy in this deal. Yeah, I mean Stallings was coming off of a three win season, a gold glove winning year and like I mean this was the opposite of the Josh Bell trade, right? Where like Stallings is at his peak value. Uh now Stallings after this kind of tanked, but I feel like you could have gotten more for Stallings than this. Um but I’ll give this a C as well. Yeah, we’re loading up the C category right now. I’m gonna go with C there. See, like that isn’t even good enough to hit B. Like that just shows how bad this has all been. Um, if this one could be a B, though, just because of I guess if if you want to count Nicholas like still being there and the potential that he has. I could be talked into that being a B. But I mean, Songs was coming off a really good year. We could put this in high C and then the chat down below could say put it in B as we go on and Kyle Nicholas’s career. Um, but he’s been up and down in this major his in his major league career so far. Like last season Kyle Nicholas looked pretty solid towards the end and then the start of this major league season he’s not looked as good. Um, and he’s still in Triple A. So, we’ll see how that one goes. This one is this next one here. Daniel Vogelbach, a player for player for Colin Holderman. I think this one is a weird one and I’ll just give my reasoning really quick. Um, I’ll put it in it’s low C, high D. I’m stuck between it because the thing is Daniel Vogelbox now on the coaching staff. So, it is a full circle trade. Um, I want to go see because most of the time Holderman has been good. Most of the time he’s been serviceable. This year we’ve seen the most awful version of Colin Holderman where it’s like, “Oh, here he comes.” Um, but like last year, the first half he was pitching like an all-star and then it just fell off. So like his first year and a half as a pirate was good and then his last year and a half as a pirate has been pretty bad. So I don’t really I don’t know where where are you thinking with this one before like we kind of said it like this is a weird one. Yeah. Um, Daniel Vogelbach, I think people forget about like how good of a hitter he actually was just, but I mean, out of all of the the free agent signings that we’ve had to play first base, like Vogelbach was the best one. Um, I mean, he had a 115 weighted runs created plus before getting traded to the Mets. Then he had a 142 weighted runs created plus with the Mets. Um, that was also a deal that came with an option on it. So, the Mets picked that up and then he gave him a 108 weight runs created plus the next season. So, like you’re looking at a guy who hit during this deal um while the Pirates were trying to find first baseman all this time. Holdman, the stuff’s great. He’s had his ups. He’s had his obviously his downs. I guess I’ll give this a C. That’s where I’m thinking too. And there’s a lot of C’s here, but it’s like it’s one of those trades where like it it doesn’t it doesn’t really it didn’t really help you. It didn’t really hurt you. Jose Canana to the Cardinals for Chris Stratton, Johan Oeda, and Malcolm Nunees. Oedo is probably the prize of this deal. He’s been injured a lot. Um I mean, I like what I’ve seen out of. Um Malcolm Nunees still in the system. I might go B. It’s very I go B at a minimum here. Um, I could I you could even lean A, but I think B’s solid. Uh, I mean, they they found a starting pitcher who gave him 177 innings in 2023 for two months of José Canana. So, and he’s and he’s working his way back. So, I’ll give this one a B. I like Odo. Okay, that’s a good one there. So, that’s one of our higher ones. That might be the best one we have on this list so far besides the Frasier for Jack, I would say. Um, this next one I actually kind of liked. Kevin Newman to the Reds for Dari Moretta. Big bank. I’ll give that an injured pitcher. Yeah, I’ll give that one a B. I mean, Newman Newman doesn’t didn’t have a ton of value and they got they got a useful reliever in return. I’m going to go with that as well. Um, this next one I also liked Nick Garcia to the Rockies for Connor Joe. He was serviceable. I mean, yeah, I’ll go be there, too. Robert Stevenson to the race for Alica Williams. I’m going D. Um, D. D’s D’s being generous, but yeah, we can go we can go D. You want to go F? That was an awful trade. I hate it at the time. D at best. Okay, we’ll go D. Um, next, Carlos Santana to the Brewers for Johnny Severino. It’s hard to hard to grade this one with Severino still being so far away. Um I do I do like Severino. Uh I think he’s got some gaps in his game, but uh you probably could have gotten more than that. Maybe I’ll still put this in the C category just because I’m not really sure. Yeah, I thought Carlos Santana could have got a lot more. Um, the fact Vogleblock at the time got a serviceable player compared to Carlos Santana, kind of weird. Um, this next one though, probably one of Ben’s best trades. Um, probably know where I’m going with this. Rodo Castro to the Phillies. This one came out of nowhere for Bailey Falter. Is this our first A or is it not good enough still? I’m gonna put this one in the Do we Do Do we want to keep I mean, you’re still looking at a guy like I mean Falter’s been Falter’s been a pretty decent backend starter, but I mean since the trade, you’re still looking at 1.9 war. Like, can you really put that in a category? Like, the Pirates definitely won this trade, but I’d put this more in a B. Is this probably the highest one in B? This is probably the highest one in B. This next one, a couple quick ones here. Rich Hill and Gman Choy to the Padres’s for Jackson Wolf, Alfonso Revas, and Estor Suero. A weird one. Yeah, they got a lot in this one. Um, and honestly, Revos is a guy who you probably could have gotten away with um keeping him a little bit, but uh I’ll go I’ll go C on this one just because Swero still has a little bit of upside. Okay, we’ll go C. Hedges to the Rangers for international cash. A A+. That’s That’s the A. Yeah, this is our first A on the list. Maybe only one. Austin Strickland to the Giants for Joey Bart. This is How are we grading this? I’m gonna say this is a this is a B. Uh the Pirates were in desperate need of a catcher last year and they got Bart for I mean it’s not like Austin Strickland is doing anything. Uh he’s hasn’t made it above high a ball. I’ll give this a B. One of his better trades. I mean, Bart, we’re not happy with Bart right now, but he’s on the team. Yeah, I’m fine with B. Um, based off how he’s playing this year, it’s a very low C, but I’ll I’ll I’ll stick it in B just because he got the best out of Bart’s entire career, and now it seems like he’s gone back to his career normals. Moving on to a very infamous trade deadline week. Um, this was probably Ben’s first time as a buyer for the Pirates, and it’s probably his last. Quinn Priest to the Red Sox for Nick York. We’ve seen Quinn Pier a lot in the news lately. Um, yeah, he was traded to the Brewers from the Red Sox, though. So, what do we think about Quinn? You know, at the time of the trade, I didn’t think it was that bad, but then you look and see what Boston got for him and then what he’s doing this year in Milwaukee and and it it stings a little. Um, and York has York hasn’t made the majors yet this year. They haven’t they haven’t played him at all. I’m gonna put this one at a like right now this is a D. I’m going to put it but like there’s this could change like depending on what York does it could change but like Nick York hasn’t made it made the team yet and we’re 22 games under 500. Moving on. Patrick Riley prospect for prospect for Billy Cook. Um D. Yeah. I don’t like what I’ve seen about Billy Cook so far. I think we can kind of agree on that. Hasn’t even been playing like it. I mean, yeah. Yeah. The infamous Charles McAdoo to the Blue Jays, a fan favorite for IKF. I like this trade. And like I said, Isaiah Connor Falefa is a player I like having on my team. I don’t think he’s being used right, but I mean, I’m going to give this a I’m going to give this a solid B. I was going to say, does that have a chance to push A? I don’t think it has a chance to push A, but I think this is a solid B. I’m fine with B. Um, nothing will touch touch hedges for international spending money. Um, this one might be an F. The infamous we’re buying in move for an outfielder. We were all waiting for one. John Chuck Shim, Garrett Forester to the Marlins for good old BDLC. Brian Dook Cruz. Yeah, this is an F. Uh, I mean, just an absolute disaster of a trade. You didn’t give up anything for him, but like just getting him on your team made you so much worse. Yeah, that one stunk. A lot of people compared his bat and on Savant to Edward Olivaris. Um, at the time I was like, we got a home run guy, but then he just did not fit at PNC Park. And I think he hit two home runs the rest of the season and they didn’t even keep him. He could have been a pirate right now and he is now in his second organization since Pittsburgh. So, he was probably very upset he left Miami because that was his perfect home. This one has a lot of fans up in arms. Um, Luis Ortiz in trouble right now with gambling. Michael Kennedy, Josh Hardle to the Guardians for Spencer Horowitz who was traded that day for Andre Jimenez. So, Horwitz was on two teams, well, three teams in one day. So, what do we think about the current Pirates first baseman? Um, well, so far hasn’t been good. 71 weighted runs created plus negative.2 war. So, as of now, like this tra like you gave up a lot for him, too. This is a this is a D at this point. Yeah, I think it can change, but right now this is a D. They still have him under contract like league minimum at least. He’s going to be here for a while. Who knows? Maybe they even move on from him if their new GM comes in, which would just be crazy. Um, it helps Luis Ortiz is in trouble and might not pitch for a while, I guess, but I’ll go D as well. And I I believe in Horwitz, but like it just hasn’t worked out. And then we found out he has a wrist issue and that made it even worse. Um, yeah, like I think this trade will eventually move into like C or B status, but as of now, July 20th, 2025, it’s a D. Finally, we just had this one. Adam Frasier to the Royals for Cam Deainy. Um, I’m gonna say it’s C as of now with the potential to to move up or down. Am I crazy for putting this in B just because they got a player for him? I wasn’t expecting them to get anything out of Adam Frasier. I could be talked into a P. They got somebody. Do we want to go with B? Sure. That would make two Adam Frasier B trades. Hey, there’s a common uh common denominator. So, looking at my list right here, the best trade of the Ben Cherington era was Austin Hedges to the Rangers for international cash. Thank you all for watching today’s episode here on Northshore 9. Make sure to subscribe to the channel down below. Hit the bell for post notifications to make sure when the guys are live and when you get more videos like this. Make sure to follow us all on all of our social medias and make sure to, like I said, leave a like on the video as well and leave a comment down below on your thoughts about our tier list that Gemini made here today and some trades that weren’t on this like a Roanzi Contraras trade that didn’t make the video or even just something like the Alexander Canario for cash considerations deal. So, make sure to do everything like I said, subscribe to the channel, leave a like on the video, follow us on our socials, and we will see you next time. And as always, let’s go Bucks.

Ben Cherington has made a lot of trades since taking over as GM of the Pittsburgh Pirates — but how many of them have actually worked out?

In this video, Nathan and Jim break down and tier rank every notable trade Cherington has made during his time in Pittsburgh. From the controversial Josh Bell deal to the polarizing moves involving Clay Holmes, Joe Musgrove, and Starling Marte we dive into what he gave up, what he got back, and how each trade looks in hindsight.

Which deals were steals? Which ones were disasters? And which ones… make you question reality?

Watch the full breakdown, drop your rankings in the comments, and let us know:
How would YOU grade Ben Cherington’s trade history?

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