Hold My Cutter
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Hold My Cutter
Building A Winner Through Player Development "A Look Back"
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What actually turns a struggling franchise into a contender? We dig into a people-first blueprint for the Pittsburgh Pirates that prioritizes player development, modern pitching, and a culture of humility and feedback over quick fixes. From the first conversation, the focus is clear: winning is hard everywhere, and sustainable success depends on great players supported by a smart, collaborative environment.
We walk through why Pittsburgh is the right stage, how alignment with ownership sets the conditions for real investment, and why a player-centered philosophy can move the needle more than any single splash. You’ll hear how development becomes a compounding engine when 200-plus players each improve a bit, and how that philosophy connects scouting, coaching, analytics, and high performance into one clear system designed to raise the entire roster’s baseline. We also share lessons from Toronto on modern pitching: blending pitch design, biomechanics, and data with on-field translation so pitchers understand not just what to change, but why it works in-game.
Culture ties it all together. Humility is treated as a performance tool—the base layer that makes learning possible—while active pursuit of feedback keeps blind spots from calcifying. We break down how to invite dissent, hire diverse thinkers, and give coaches and players a voice that actually shapes decisions. And when the team earns its shot? We talk about responsible risk, signaling belief at the right time, and making moves that push a good club toward October without sacrificing the future. If you care about how real baseball organizations win—through people, process, and clear-eyed choices—you’ll feel the plan taking shape.
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And what are your thoughts about coming to Pittsburgh?
SPEAKER_00:Uh what I feel is gratitude and excitement. You know, gratitude for the opportunity to be a part of building something special and in a place that for a team that really matters a lot to a city and a region and a fan base. And um gratitude to Bob Nutting and Travis Williams for having a faith in me to be a big part of this process. And and then excitement just to dive into the work, you know, dive into figuring out where the opportunities are to get better and ultimately build that winning team. But real challenges here, are they not when you look at this situation now? Challenges everywhere in Major League Baseball. It's a it's a you know it's hard to win a Major League Baseball game. Uh doesn't matter what city you're in. Uh so you need great players, uh, great tactics, great environment. And um I'm excited and feel grateful that I've had 20 plus years of experience to, I think, learn a lot about what really drives that winning. Um, and I'm excited to bring some of that uh here and combine that with a great intelligence that I know already exists here and uh and get to work on building the winner.
SPEAKER_01:Well, Ben, why Pittsburgh? Because you certainly had other opportunities elsewhere. What made this such a great opportunity for you?
SPEAKER_00:Yeah, I think two things really um predominantly. One is that uh I do feel that the things that I have the most passion for uh in identifying, helping to identify and develop players and really find the people uh that help to do that, help whether it's scouts or coaches or analysts, uh other so other sources of expertise, high performance, uh, you know, that that is my passion is is helping people figure out, you know, how do I identify and develop players? Um and so and I feel like those are the things that are gonna matter, particularly in a place like place like Pittsburgh to give it a chance to win. Um and then second, you know, the opportunity to get to know Bob and Travis, I just I came to really have a strong feeling about who they were as people, um, people who I'd want to go to work with every day, who I'd want to get feedback from and learn from, um, and certainly got a really strong feeling about their level of commitment and emotional connection to the pirates and the city of Pittsburgh. So uh combination really of that, where I think it's a real personal fit based on my passion areas and experiences and uh wanting to go to work with Bob and Travis. What did you know about Travis? What do you know now about him? Um got to know him through the interview process and just found him to be, you know, just a really good combination of intelligence, curiosity, warmth. Um, he, you know, certainly can think strategically. He's been part of really successful organizations. One of the things that appealed to me uh about working with Bob and Travis was the opportunity to learn from people who have had different experiences, people outside experiences outside of baseball. Um, in the most effective uh environments that I've been in, it's been when a uh a combination of people with different perspectives come together to collaborate on a decision. I feel like we'll be able to create that here uh with the with the combination of experiences we're bringing. And that that's exciting to me.
SPEAKER_01:I think when Travis Williams uh was announced, he said something like, I wouldn't be here unless I was absolutely convinced that Bob Notting wanted to win. I assume that's the case with you.
SPEAKER_00:Yeah, that was loud and clear uh through the process. Not you know, in both in terms of his uh real emotional connection to the Pirates and Pittsburgh and desire to win, um, but also in terms of his uh level of understanding of what it was gonna take to win and the investment uh that's been that's been made and will continue to be made in the entire baseball operation, including the team. Uh I'm confident, and I wouldn't have I wouldn't be here if we didn't share that vision of of winning and a belief that we can attain that.
SPEAKER_01:So you're convinced that he will provide you with the resources necessary for the Pirates to win. I am very confident of that. Your background is scouting and player development. It's a well wide variety in baseball with you of all these years. But you you talked about the passion. Is is your greatest passion that development, that the the players to see them from the ground up?
SPEAKER_00:Yeah, if I was gonna point to one thing, um, it would be player development, and that is probably driven by, first of all, I have a deep belief that this game has been, is now, and always will be about players. Uh it is a it ought to be a player-centered game. This is what this is why we're all here. Um so if you think about it in that way, then you know, one of the most important things we can do, of course, is to help players develop. What are the re what is the environment? What are the resources, what is the areas of information that players need to uh develop skills, ultimately reach their uh their their peak in performance. And ultimately that drives winning. You know, if you think about uh 200 plus players in an organization, well, if all of those players improve, uh that is a much uh larger uh turn on team improvement. You're turning the dial much more than acquiring any single player from the outside. Uh so it's really that collective improvement, at least in my experience, that has driven success more than anything. Now, of course, we have to identify and acquire players really well, too. Um but that player development has been an area I've been involved in intimately throughout my time in baseball, and it's an area I care about, I think partly uh driven by that feeling that this game is about players.
SPEAKER_01:Ben, most recently you're at the Toronto Blue Jays. Talk about the philosophy that you had when it came to pitching and developing pitchers.
SPEAKER_00:Yeah, you know, one of the reasons I went to Toronto after leaving Boston uh was that I really wanted to commit to learning about the most modern and cutting-edge uh techniques in pitching development. Um, as a GM in Boston, and even in the job I had before that, I just didn't have as much time to dive into that. Um, but in Toronto I did, and I knew that that was going to be a really important part of our process in Toronto. And I also knew there were people there in Toronto who had done that before and I could learn from. Um so I was involved in a lot of things, but I certainly spent a lot of time learning about pitching, relearning about pitching and pitching development. Um, and I'm grateful for that time because it's such a critical piece of what every team is trying to do, but certainly a critical piece of what we're gonna need to do here with the Pirates.
SPEAKER_01:And I mean, can you win without pitching?
SPEAKER_00:Well, you you can't, you you've got to have everything, right? Like the teams that are really winning have a great group of position players, a great group of pitching. Um, but pitching is so critical, and certainly without it, uh it's pretty much impossible to win.
SPEAKER_01:I read somewhere uh that a a friend described you as a person who's, quote, accountable as well as unflappable. Never been impressed with what he's accomplished. Another friend said, persistent, determined, and humble. Good descriptions of Ben Sherrington, you think?
SPEAKER_00:I hope so. I think so. Um the unflappable part, I'm probably not not, I don't score a hundred on that one, probably. Um but I hope the other I hope the other words fit. Certainly, I think I think humility is the is the is the foundation of learning. And you know, if if we're not humble, it's really hard to learn. And and learning will be a critical part of the culture that I would want to be a part of here with the Pirates, whether it's baseball operations group, whether it's our our major league uh clubhouse environment, whether it's player development, scouting, uh, we've got to be a learning organization. And in order to be a learning organization, you have to have uh a humil a base of humility. Uh if not, then you know you're a lot less likely to learn if you have if you think you have things figured out. So that humility is important and certainly um something that we are looking to foster and in hiring, looking to uh find people who are both humble and competent as it relates to that continuous learning.
SPEAKER_01:Do you still see then some some good things in the current pirate system? Because the question is going to be are we in for a rebuild?
SPEAKER_00:Well, for sure there's good things. Um there's good players on the major league team, there's good players in our system, um, and there's good people here too. I'm confident of that. Uh we just need to get better. You know, we need to get better everywhere, you know, in order to get uh win more baseball games. You know, that's and that's the bottom line. Like that nobody nobody does these jobs, nobody works in baseball operations, certainly players most importantly, don't do their jobs unless you want to win. Like that's that's what we're here to do. Um so you know, we the Pirates didn't win enough in uh 2019, so we need to improve on that. We just get to get better every day and in every aspect uh of the operation and build on the strengths we have.
SPEAKER_01:Ben also saw someone, a writer I think said that Ben Charrington was unafraid to swing and miss. So I guess that means when maybe the team is close, in this case the Pirates, you you'll go for it, as the pirate fans like to say.
SPEAKER_00:Well, I think, you know, I think if you're a player, this again, get you know, my feeling about this game being really sh ought to be being player-centered. And um, if you if you put yourself in the shoes of a player in a clubhouse and you're working hard every day individually, collectively, um, and you're performing at a level where the team's winning games, and the team is in a position uh to win and have a chance to do something special in October, um, then I do feel it's our obligation to try to help that group of people uh accomplish that. Now, there's a different ways to do that. We still need to be mindful of risk and mindful of doing things that might um where the the value proposition you know shifts the other way. You know, we that there's different ways to look at that. Um but I think that we're we're asking players and coaches at the major league level to work extremely hard to perform at a very high level. And when they do, um, it's our job as a partner to them, you know, to help them, to help them, you know, push over. And you know, maybe it's getting that final piece to, you know, win a few extra games in October. So I do feel that's important. Um, of course, we've got to look at all the variables that go into that. Um, but I if I was a player in a in a clubhouse or a manager or coach, I'd want to feel like the front office is doing that.
SPEAKER_01:You probably understand about fans' frustrations because of what you went through in Boston. Sure. And now Pittsburgh seeking the pirate fans, seeking that world championship. So you can you can relate.
SPEAKER_00:You know, passionate fans um are what drives you know us and a team, and that interest in the team is so critical, and it's at the heart of you know the best fans and certainly pirates fans. And when you have that level of passion, of course, that's going to turn into frustration if the outcomes aren't good or good enough, or or you know, there isn't enough uh consistent success. So I certainly, and I and I was a fan way before I was an executive, so I certainly can relate to that. Um and really, you know, our job is to, you know, work our tails off every day in a really honest way to get better every day, so that ultimately we put a team out on the field uh that our fans can be proud of and that they see uh a direction and a team that's growing into a winner.
SPEAKER_01:It sounds like you're one of your you're talking about passion again, but what you really love about this job is gathering not just the information but the people for one purpose.
SPEAKER_00:Yeah, I mean, you know, look, it it I every every uh everything that we do in baseball, uh whether it's um identifying a player, whether that's an amateur player, international player, or professional player, whether it's you know the process of acquiring that player, whatever channel you're acquiring the player through, whether it's helping develop the player or put that player in the best position to succeed, all of those activities are driven by people. At the end of the day, human beings are doing that. Um, even if you're using information and data, there it is a human being analyzing that information and data, processing it, and making recommendations. Uh so human beings are doing the work of baseball operations and ultimately will um ultimately will help us win baseball games uh in people in Pittsburgh. So I do have a deep passion for people and finding the best people in all of those areas because I know that we can't be great at all those areas uh without the best people. And those people have to come from different backgrounds, different perspectives, different strengths, different skill sets, um, and it's a collaboration of those people. Uh it's it's a true collaboration of those people that leads to the best outcomes.
SPEAKER_01:So you just touched on something. You're one who, when it comes to hearing, you like to hear all sides, uh, including those that may disagree with you. Because some uh leaders don't care for that. Yeah.
SPEAKER_00:I mean it's critical. And and you know, I think that the the one of the critical um I think skills for a leader is actually pursuing that feedback. Because sometimes um in a job like this, if you don't really pursue the feedback, um make clear that you need it, uh, you don't always get it. Because um sometimes people may feel like, well, because of that person's position or title or whatever, um, we're not allowed or shouldn't, or you know, we're not comfortable giving that feedback. So it's really up to us in the in these jobs to pursue that feedback, make clear how critical it is. Um, I know for a fact I can't do this job as well as I want to uh without consistent feedback. The feedback so that feedback can come from Travis, it can it can also come from any member of the baseball operations team uh or others, and certainly our put our players included and coaches, etc. So uh feedback feedback is a critical element of learning, and we have to be a learning organization.
SPEAKER_01:I would think that a guy like Ben Sherrington, that's a marquee name in baseball, a marquee general manager was just hired by the Pittsburgh Pirates. I'm gonna stress again from my vantage point that Ben Charrington doesn't come to Pittsburgh unless he believes there is a strong commitment to win. You're not just taking any job, in other words. You know, you didn't you you can't again, you could have taken any job, you could have, and you have been offered others in the past, but you decided to come to Pittsburgh with a belief that this team can win. Yeah.
SPEAKER_00:I'll let you use the word marquee, because it's certainly not not that's not the word I would use. Um but um yeah, I do feel this is uh the the perfect opportunity and really the only opportunity uh in this particular job. You know, it was hard to leave Toronto because I loved what we were doing in Toronto and the people there and uh felt really connected. Um but if I was gonna do this job again, this was the place to do it, and uh and this is the only place I want to do it. I hope it's the last time I do it. Um and I'll and I'll and we'll just work as hard as we can to build a winner. Plus, you get to be the best league of all, too, by the way. Welcome, welcome, and this that will be a new experience. So looking forward to that.