Jed Hoyer thought he experienced a once-in-a-lifetime thrill in 2004 when he helped the Red Sox break their 86-year curse. Little did he know he would not only have another opportunity to make baseball history, but it would be in a place even more starved for a World Series title than Boston.

Hoyer joined old friend Theo Epstein after the 2011 season, leaving his position as the Padres' general manager to take the same job with the Cubs. Five years later, Hoyer was doing the previously unthinkable: riding in a Cubs championship parade.

MLB.com recently sat down with Hoyer at Sloan Park in Mesa, Ariz., to discuss his days with the Red Sox, his decision to rejoin Epstein in Chicago, what Kristopher Bryant might do for a follow-up act to his National League MVP Award-winning season, and what might have happened if Boston had traded for Alexander Rodriguez .

:: General manager Q&As ::

MLB.com: You were 28 when you landed your first job in pro baseball: an internship with the Red Sox. Was that always your goal or was it something that hit you in your late-20s?

Hoyer: It was always a goal. I always tell people if I could do it again, I would be a lot more persistent than I was. I applied for a lot of jobs when I first got out of college; sent letters, didn't really go about it the right way. I definitely wasn't dogged enough in my pursuit of a job. I ended up having a bunch of different jobs over the next four or five years and found out about this internship with the Red Sox through a friend. I knew Ben Cherington; we played against each other in college. That presented itself and I went after it really hard. The answer is yeah, I always wanted to do this; I didn't know exactly how to go after it. Pre-Moneyball, there wasn't sort of an awareness that people like me were being sought out for jobs like this in some ways. If I could do it again, I'd be a lot more dogged and maybe I would have gotten in at 23 or 24. But I actually think the jobs I had helped me advance quicker because of some of the skills I learned in other jobs. I guess it worked out well in the end, but I definitely didn't take the most direct route at it.

• PODCAST: Listen to the full interview

MLB.com: Cherington once joked that the Red Sox in 2002 "felt like a startup" when new ownership took over. Did the franchise need that kind of reboot?

Hoyer: In 2002? I think so, yeah. At the time, 2001 had been a really ugly-season chapter for the Red Sox. Very negative clubhouse and the overall vibe around the team was not positive. I don't think it was a destination at that point, so I think at that moment, it did. It had been a relatively small front office; front offices were smaller then, and the Red Sox had a small front office even by industry standards at that point. Some of those people left before we got there. I've always said, to me, one of the best things that happened to my career was simply being hired by the Red Sox. There was opportunity everywhere, because it had been such a small front office. People that were titled "interns" were forced to do so many things that were above our experience level because we didn't have a lot of people. People that came on five years later came into a much fuller front office with much less upward mobility.

MLB.com: We all know about the trip that you, Theo and Larry Lucchino took to see Curt Schilling in Arizona on Thanksgiving of '03 when Schilling agreed to that trade to come to Boston; did you guys have the sense that he was the piece that was going to put you guys over the edge?

Hoyer: I think we felt really good. We knew we had beaten out the Yankees to get Schilling; it was really a two-team race to get him. We knew how much the Yankees were kind of waiting in the wings, hoping our deal fell apart so they could jump in. At that stage, it was Red Sox vs. Yankees. I felt like our offseasons were sort of spent trading punches back and forth. People always talk about the Thanksgiving with Schilling; three weeks later, Theo and I were in New York meeting with A-Rod for two nights. I remember the feeling that I had, I think it was the day before I left for Spring Training, being in the office and finding out that the Yankees had acquired A-Rod. It felt like that was their punch right back. That was just the nature of that era. I've kind of accepted the fact that I don't know if I'll ever experience anything like that with two teams going back and forth like that. It was a wild experience and a wild way to start the early part of my career.

MLB.com: I know this usually is something for us media types to do, but do you ever think of what would have happened if the A-Rod-to-Boston trade had actually happened?

Hoyer: Yeah. It's interesting to think about, for sure. The second part of that deal that no one talked about was the fact that we were going to give up [Jon] Lester; that would have had an effect later on down the road, more in '07 and '13, than it did early on. At the time, A-Rod was the best player in baseball; he was playing shortstop and hitting 50 home runs. Obviously Manny was a huge part of those teams. The easy answer is that '04 wouldn't have happened because it would have been a different mix, but I think Alex would have played pretty well in Boston, as well. Who knows? I don't think we have any idea, but it's kind of wild to think about now.

MLB.com: As a New Englander raised in New Hampshire, what was it like to be a part of the group that helped end that curse?

Hoyer: Obviously it was incredible. Growing up in that area, knowing how much it meant not just to Boston or Massachusetts, but the entire region. That's one thing that's really cool about working for a truly regional team; anywhere you go all over New England, there are Red Sox hats. It was wild. It's a lot different perspective for me now, having been a part of the Cubs as well, thinking about the differences in the two things. But certainly, being from New England, watching '86, seeing how people believed it could never happen -- and watching us lose a 5-2 lead in Game 7 the year before to the Yankees, it was an incredible experience. I'll never forget driving back from the airport after we landed after beating the Cardinals; the scene on the way back to the ballpark with everyone getting out of their cars, construction workers cheering from the 18th floor on scaffolding. It was the most wild scene, just watching the whole city come to a standstill.

MLB.com: About a year later, you and Ben were named co-GMs in December 2005. Theo returned 44 days later. It was a short stint, but an impactful one; you guys pulled the deal for Josh Beckett and Mike Lowell during those 44 days. How rewarding was it to see that trade work out the way it did?

Hoyer: It was very rewarding. The way the trade impacted the team was a valuable lesson because Beckett dropped a 5.00 ERA in the first year and Hanley Ramirez was the Rookie of the Year, so it certainly appeared that deal was under water after year one. Year two, Beckett finished second in the Cy Young, was completely dominant in the postseason, we win the World Series, and Lowell is the World Series MVP. It was a good lesson that when you make a deal, you can't worry about every up and down of that deal; you have to believe in what you did and realize that the first year of a deal that's going to impact you for four or five years doesn't define the deal. That deal didn't look great after '06; it looked great after '07.

MLB.com: When you left San Diego as GM, you said you were not looking to leave. What tipped the scales for you? Was the opportunity to join Theo and the Cubs a no-brainer when that presented itself?

Hoyer: I wouldn't say it was a no-brainer, because I loved San Diego and I loved what we were building; I felt like we were on the right track. I loved the staff we had brought in. I don't think you can pour yourself into something for two years, don't see it to conclusion and say leaving is a no-brainer; that part was really difficult. But 2004 had been such an incredible life experience for me; there's one more chance in sports to do it. That part of it, how do I turn down an opportunity to do something I never thought I would have experience again -- and really on an even bigger stage than Boston. That part certainly tipped it. The opportunity to work with Theo and Jason (McLeod) in a different setting was really great. Theo and I talked about not only doing it, but doing it with the same group of people, (that) was really exciting.

MLB.com: The dynamics of your front office are a little different with you and Theo. Does your longstanding relationship with him make this work easier than it might if it was somebody you didn't have that history with?

Hoyer: Yeah. I'm not saying it doesn't work if you don't have prior experience, but I don't think I ever could have entered this relationship with someone else. I had gone from final decision-maker in San Diego to No. 2 here; giving up some of that authority, I knew that would be challenging at some level. But I also knew that with my relationship with Theo, our trust level and the autonomy that he would give me would be there. It's a really good front-office structure for the way baseball teams are run these days, but it's not without risk. If you get two people that are looking to run things, two people that have strong personalities and egos, frankly, I think it can be a structure that can lead to some big challenges.

MLB.com: Every team at this point has an analytics department; to whatever extent they use it, obviously some teams are different. Do you think teams are looking for the next big thing now that analytics have caught up?

Hoyer: Yeah, you have to. When I first got into the game, the competitive advantages on that level were much easier and would last longer. Many teams simply didn't believe in it, so if you had a belief in analytics, it could carry you a long way toward the kind of players you could acquire. I look back on the offseason from 2002 to 2003, we acquired (Kevin])Millar, Bill Mueller and David Ortiz for really almost no investment. Todd Walker, then the next year we got Mark Bellhorn; if you wanted that kind of player, they were available. That's not the case anymore. Now, teams are run in a much more similar way and the world, analytically, is much flatter. It doesn't mean it's less important, it just means that whatever those competitive advantages might be, there are smaller margins on those advantages.

MLB.com: Statcast™ has made a lot of those analytics more widely available to the public now. Do you think it's changing the way fans are looking at the game?

Hoyer: Yeah, I think in a good way. I love it when a guy hits a home run now, you're like, "How hard did he hit that?" Or a guy lines out to second and you know it was 108 mph off the bat. I do think that it's going to change the way this next generation views baseball, but I think that's a positive. It adds another layer to our evaluation. I do think it will -- not yet, but in time as we get better and better at it -- shine a light on a lot of players that previously would have been ignored. A great baserunner or a great defender will probably get his due now, where I think for a long time, not that anyone didn't believe in those things, but they couldn't quantify them. Sometimes things you can't quantify aren't believed in like homers, RBIs, runs scored and things like that. A super-impactful defender or a super-impactful baserunner now will get the credit he probably has always deserved.

MLB.com: Jason Heyward 's first season didn't go as well as he -- or you -- had hoped. Did the World Series title take a little pressure off of him heading into this year?

Hoyer: I think so. To Jason's incredible credit, a lot of times when you see a first-year free agent struggle in a new environment -- which I've seen happen a lot -- a lot of guys can go in their shell, isolate themselves from the group and feel like they're not part of it. He's such an amazing teammate, he contributes in so many other ways, it's not the least bit surprising to me that he would be the one that calls the meeting (during the rain delay in Game 7 of the World Series) and he would be the most vocal guy -- and also the fact that he has so much gravitas with his teammates that he'd be able to call that meeting.

He's a young guy, he's had a ton of success in the big leagues; his first year didn't go as he hoped, but we've got a lot more baseball for him to play here. I'm really happy the fans totally respect what he's done for the team so far, what he's sacrificed, how hard he's worked, and I think he's going to be a fan favorite once he clicks back offensively to where he was.

MLB.com: Rookie of the Year in 2015, NL MVP in 2016; what can Bryant do to follow that up this year?

Hoyer: I think he'll be better. That's the beauty of Kris Bryant. Kris loves baseball and he loves trying to get better. He said to me earlier this year, "The fun of baseball is trying to get better." Every year, he's going to go home in the offseason and try to figure out what thing in his game can he do better to have a better year next year. If you asked Kris, "Is this the pinnacle? Have you had your best year?" he would say, "No chance." He went home this offseason and what did he work on? He worked on getting back to the opposite-field power that he's had in the past. He pulled like 38 of his 39 homers last year, which is much different than he was in the Minor Leagues. I think that when you have a guy that is driven like that, who thinks that improving is fun and tinkering is fun, I think he's going to have some monster years -- and I think after those monster years, he's going to go back and try to get better. That's why he's a superstar.

Mark Feinsand is an executive reporter for MLB.com.