December 5, 2022

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How O’Halloran rose from unpaid intern to Red Sox GM

13 min read

Having grown up in a suburb of Boston, Brian O’Halloran developed his love of baseball — the Red Sox, specifically — after the club’s heartbreaking loss in the 1986 World Series. During his 20-plus years in the front office, O’Halloran has helped guide the Sox to four championship rings, but he’s just as passionate about hunting down a fifth.

I recently sat down with O’Halloran to discuss his George Costanza-like entry into baseball, his ascent through Boston’s front office, and much more in the latest edition of Executive Access.

This interview has been edited for length and clarity. Was baseball always your favorite sport?

O’Halloran: I would say it was, at least starting with the ‘86 team. Before that, it probably would have been the Celtics, just because of what they had going on in the [Larry] Bird era, but I was into all the professional sports. Starting with ’86, baseball was definitely my top sport. I was passionate about it. I played all sports growing up, but I wasn’t good at anything. You received your degree at Colby College with a double major in government and Russian studies. When you graduated, what was your initial career plan?

O’Halloran: I had spent my junior year in the Republic of Georgia, then came back home and in my senior year at Colby, I did an honors thesis on state building in Georgia, as it was a newly emerging country. When I had gotten there at the beginning of my junior year, it was the Soviet Union; by the time I left, it was its own country. I got a fellowship to study ethnic conflict in Georgia that following year, so I had an immediate short-term plan of going back to Georgia and doing research during a very tumultuous time over there with a long-term plan of probably going to graduate school for political science and becoming a professor. You ended up working for three years in Moscow supervising business operations for an international logistics company. What brought you there?

O’Halloran: When I finished my fellowship in Georgia, I was fluent in both Russian and Georgian and had two years of experience working in the former Soviet Union. I wasn’t ready to go to graduate school just yet, and I figured that if I were going to find something in international relations or government work, it would be in DC, so I moved there and looked for a job. I answered a newspaper ad for a logistics company — which I didn’t know what that was — that was seeking Russian speakers.

I ended up getting this job in this industry that I knew nothing about, but it was a growing company that was doing a lot of business in the former Soviet Union, basically handling transportation of equipment and supplies and logistics for a lot of U.S. government projects and also big commercial projects in the oil, gas and mining sectors. After about a year and a half, I was ready to move on and had an interest in going back overseas.

The company happened to ask me if I would move to Moscow, initially for a year, to represent the American side of the company in a joint venture that they had established in Russia and to oversee their operations and business development there. I ended up getting extended a couple times so I stayed for three years before I decided that I wanted to come back to the U.S. Coming from that background, what made you decide that you wanted to work in baseball?

O’Halloran: I literally sat down and made lists of things I liked in life; what do I want to spend my time doing? What do I care about? What do I have passion for? Every time I went through it, it was always baseball. “Seinfeld” was all the rage then, so I joked with some of my American expat friends that I felt like George Costanza. But that’s what I wanted to do — I wanted to work for a baseball team.

I was in my late 20s, I knew nobody in the industry and I didn’t know how it worked. But if I’m ever going to try it, it has to be now, because I wasn’t married or attached in any way, I was not in a serious relationship, I didn’t really care where I lived and I was willing to start at the bottom. I just wanted to see if I could make a go of it.

I was doing a part-time gig with the Pawtucket Red Sox to try to get something on my resume that was baseball-related and get some experience to be around the game, but I felt it was going to be really hard to come off the streets of Moscow and just start working for baseball teams, so I decided to go to business school to buy myself some time, get further educated and add some additional skills. I figured I’ll spend those two years trying to find a way into baseball, and if that doesn’t work out, I’ll have an MBA and there will be other opportunities. I went out to UCLA in August 2000. Your first job with a big league team was an internship with the Padres. How did that come about?

O’Halloran: Thad Levine, who was with the Rockies at the time, had gone to business school at UCLA and he had graduated a year or two before I got there. I got in touch with him right before or during the 2001 World Series, right after 9/11. He suggested to me that I contact this guy Theo Epstein, who was also from Boston. He didn’t know him very well, but he had heard good things and had heard that the Padres were a little bit more on the progressive side for the times and maybe they’d be open minded to an MBA intern in San Diego. I contacted Theo and he had me come down and meet [then-Padres GM Kevin Towers] and others; I was eventually able to convince them during the Winter Meetings that year in Boston to give me a shot as an unpaid intern.

It was it was a very small shop at the time, so I initially mostly worked with Theo. A couple months in, he left for the Red Sox. I handled some pre-arbitration negotiations, which is amazing because I was an unpaid intern. I was like, “When I call an agent, what do I tell them?” Theo said, “Just tell them you work for me; it will be fine.” I was able to do substantive things just because it was a small shop and they trusted me to do it, which was great. I got a chance to be around the scouts, go to games, be around the scouting director, the GM. Jason McLeod was the area scout for the Padres, so Jason and I became friends and he would show me the ropes and take me around to games, so I got a chance to learn to evaluate and be part of the Draft process. Your wife was getting her Master’s at Harvard, so you went back to Boston. Theo gave you an opportunity to sort of work for the Red Sox in the summer of 2002; tell me about those early days with Boston.

O’Halloran: Initially, he said, “Look, there’s isn’t really a spot for you — quite literally, there isn’t a spot for you. We have this intern named Jed [Hoyer], so you can come in and use his computer when he leaves for the day, which is usually around 11 at night. If you want come and chart games at night, that’s fine. That’s all I’ve got.” I said, “Yeah, no problem.” So I used to call Jed at 10, ask him what time he was leaving, then come in and sit on his computer and chart mostly Minor League games until 3 or 4 in the morning. At some point, I think they felt bad for me, so they let me start coming in during the day. For a kid growing up Massachusetts, was it a dream to be working at Fenway Park?

O’Halloran: Even with the first internship at the Padres, a little bit of the fan leaves you in that you’re around the players, you’re around the GM, so everything’s a little demystified. That said, “working” for my hometown team, coming into the office kind of like Kramer did — we used to joke about that; they would ask me what was in my briefcase and I said “Crackers.” We’re going to set a record for the most “Seinfeld” references in an Executive Access interview.

O’Halloran: I was thrilled to be able to come into Fenway Park and help out in any way I could, but most importantly, I was thrilled to be around awesome people that I was learning from, and to be part of something that we hoped would turn out to be special. I hoped I would be able to stick around. As you were doing this graveyard shift of an unpaid internship, you were also working as a substitute teacher. Did you give yourself any kind of time frame to get a full-time job before you would take your business degree and find something else to do?

O’Halloran: I really didn’t think of it that way. I just felt like I was going to make this happen somehow. I was just going to keep showing up, try to do a good job and hopefully they won’t kick me out. I didn’t let myself think about the alternative. Your first year as a full-time employee was 2004. What was it like being a part of that World Series run?

O’Halloran: It was an incredible experience. Having grown up there and been a fan in 1986, what happened then and how that impacted my life, I honestly don’t know what happens to my life if the Red Sox win in ’86. I may not have become quite as passionate; I don’t know. I’m not sure. So there was a lot tied up in it for me, personally. By that point, now two years into working at the Red Sox, the bigger part of it was about trying to be part of something special and having a small role.

As an organization, for us to bounce back from [the 2003 ALCS loss] and go through a very strange offseason, just to be part of that with this group of people that were trying to win a championship under all those crazy circumstances in Boston, it was just an amazing experience. Every single member of Theo’s tree has made reference to the culture he created in that organization. What makes it so special?

O’Halloran: Theo really pushes people that work for him. He cares so much about winning and being a great organization, but he also cares so much about the people that work with him. Everybody feels that. It’s a special gift that he has for making people feel a part of something and that their role matters, but demanding a lot out of them. We’re all in this together, we’re going to have a good time doing it and we’re going to break some stuff along the way – literally. We’re going to push ourselves to be the best. What was your biggest takeaway from your time with him that you’ve tried to take into your own career as it’s moved forward?

O’Halloran: From the standpoint of building a baseball team, it’s the importance of the pipeline — scouting, player development, analytics, whatever goes into making sure you have the talent and that you’re doing everything to cultivate the pipeline of talent coming into your organization, keeping one eye on the present and one eye on the future to try to create sustainable success.

That’s the business answer. On a more softer or personal level, it’s doing what you have to do, making the tough decisions that you have to make and being objective and clear-sighted about that and compartmentalizing emotion that comes into difficult decisions while still caring about the people involved in making sure that they know that you care about them. You start moving through the front office over the years; two years as the manager of Major League administration, five seasons as the director of baseball ops, you get moved up to VP of baseball ops in 2011. At some point, do titles ever start to matter?

O’Halloran: I didn’t honestly give a lot of thought to what the highest title I might end up getting in baseball would be. After a while with the Red Sox, I got married, had kids. Both my wife and I are from the Boston area. I grew up rooting for the Red Sox, so I really wasn’t interested in leaving. I would listen and consider opportunities that come up if they do, but I was very happy being a contributor to the Boston Red Sox. My goal was to help the Red Sox win championships and to build a great culture. I did enjoy being part of the leadership more from the standpoint that it’s on us to do this whether it was with Theo, Ben [Cherington] or Dave [Dombrowski]. I did have opportunities over the years to move up; it’s just the way it worked out and that was great. But that wasn’t the goal. You were part of the four-person group that led the team after Dave left with Raquel [Ferreira], Eddie [Romero] and Zack [Scott]. One of your duties during that time was to hire Dave’s replacement. What was that process like?

O’Halloran: Ultimately we understood that it was going to be ownership’s decision on what would happen. The way I approached it was that we were sort of stewards of the baseball operation; wherever that lands weeks or months from now, we have to do a really good job. There’s staff to hire, there are decisions to be made, preparation to be done for the offseason. We were mostly focused on trying to do a good job on behalf of the Boston Red Sox, no matter how it all panned out beyond that. When Chaim Bloom was hired as chief baseball officer, they named you GM. When it was announced to the baseball operations department during an internal meeting, the room exploded with applause. What did that mean to you?

O’Halloran: That’s a tough one; it makes me emotional. That meant a lot. It goes back to what’s important, which is relationships. I don’t think it was about me. I think it was about a feeling in an uncertain time of continuity. It was before any of them had met Chaim. We delivered the message to the group and we said, “This is this is great news.” I knew Chaim before he came in, so I could say, “You guys are going to love him. He’s great. He’s going to help us get better. It’s going to be good for everybody and good for the Red Sox.” When one of the other folks in our quartet mentioned my new role, I think a lot of it was like, “OK, there’s going to be some continuity in leadership helping run the department that knows me, that knows us and that knows what we’re about.” Dave used to call you “Bulldog” for your tenacity in negotiating contracts. Do you like that process?

O’Halloran: I do, but not for reasons that may be implied by Dave’s nickname. After doing this for 20 years, I enjoy the relationships I have with the agents, I like trying to find a solution. Even when it’s difficult, those are good challenges. Those are fun to try to navigate; it can be frustrating at times, but I do enjoy that. You have worked with Theo, Ben, Jed, Allard Baird, Mike Hazen, Dave, Chaim — guys who have done some really big things in this game. Have you tried to take something from each of them to help shape you as an executive as well through the years?

O’Halloran: When you’re around good people, if you’re not learning from them, you’re doing something wrong. The approach I take, especially as someone who came into the game without playing experience or a ton to offer initially other than working hard, I just need to be learning constantly, whether it’s from a scout, from Theo, from a coach or from an entry-level employee in the front office who just got out of college and knows how to do things that I don’t know how to do. To be able to learn from Allard, who was a GM, from Chaim, my goal is to always be learning. The game is changing all the time, so if we’re not learning, we’re falling behind. What’s your favorite part of the job?

O’Halloran: It’s the baseball part. It’s trying to fit the puzzle pieces together with a group of people, all pulling on same end of the rope to build a winning team. Being at the ballpark with your colleagues trying to figure out ways to get better. Not just the front office group, but coaching staff, the manager, player development folks. I love the Draft; that’s a meaty baseball task, trying to figure out the best way to make the Red Sox better with a group of people. I love the adrenaline rush of the Trade Deadline and the Winter Meetings. You’ve been here for four World Series championships; which is your favorite?

O’Halloran: I don’t really have a favorite, honestly. They’re all special. As a greater Bostonian, the obvious and easy answer is 2004. As a Red Sox baseball operations leader or staff member, you can certainly make a case for ’07 or ’18 in terms of players coming up through the system and making an impact to help us win a World Series. There’s a lot of pride in that. 2013 was special for a lot of reasons, obviously the marathon bombing and how that group of guys came together. I’ll take any one of them any time. What motivates you to get the fifth ring?

O’Halloran: This is what I’ve dedicated my professional life to, so that’s what we’re here for. We’re here to win championships. I get to come to Fenway Park to work, so I know how lucky I am. If I can’t find motivation to try to win a championship, I don’t know what would be wrong with me.

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