When he began his internship with the Yankees in 1986, Brian Cashman didn't envision a career in baseball. When he was named the team's general manager in '98, he knew the shelf life on such jobs under George Steinbrenner were typically shorter than most.
Cashman enters his 20th season as the team's GM, looking to lead the Yankees back to the top of the mountain for the first time since 2009 -- an eight-year drought that feels like a lifetime in the Bronx.
MLB.com recently sat down with Cashman in his office at George M. Steinbrenner Field in Tampa, Fla., to discuss what he learned working for The Boss, what it was like being a seller for the first time at last year's Trade Deadline and how he hopes the current youth movement will bring a 28th title to Yankee Stadium.
• PODCAST: Listen to the full interview
MLB.com: It is well known that you began with the Yankees as an intern in 1986. Could you have imagined at the time that you would still be with the organization more than 30 years later?
Cashman: No. Staying power was not something that was synonymous with being a Yankees employee.
MLB.com: Did you always want a career in baseball?
Cashman: I wanted to be a player. I think anybody who plays the game, they play it because they love it, and I was no different than most kids; dreaming that one day you could somehow find your way into professional baseball. Obviously I wasn't good enough for that. I never had any aspirations of being a front-office executive. That was never something I ever thought about.
MLB.com: When did that turn for you?
Cashman: I got a chance to do an internship with the Yankees, and even once that led to a full-time position, I still never looked at it as a long-term career. Once I got the opportunity to grow with the Yankees -- I became the assistant general manager, four years under Gene Michael and two under Bob Watson -- during that time frame, I still was thinking about going back to college, getting a master's degree in something, whether it's going to business school or law school. In my mind, I was having these discussions, "What's in my best interest? Do I tag out as the assistant GM of the Yankees and go on to get a better education and get a real job in the real world?" Once George Steinbrenner offered me the GM position, obviously that stopped.
:: General manager Q&As ::
MLB.com: George Steinbrenner used to go through general managers at a record pace; he had 10 of them in the 1980s alone. How did you manage to last so long working for him?
Cashman: We had great players and we had great teams. That's the bottom line. We got out of the gate winning three straight world championships, we were in four straight World Series, should have won four straight. We kept winning divisions -- every now and then it was a Wild Card, but we had great players. Timing is everything.
MLB.com: What was the biggest thing you learned from him?
Cashman: He used to have a sign on his desk: "Lead, follow or get the hell out of the way." He talked about how it's lonely at the top when you're having to make the final calls. When you're sitting in a bigger chair and you have to make difficult decisions, a lot of times you're flying solo missions. You get everybody in a room, you get their input -- but at some point, somebody has to make a final call. And in many cases, it's not popular. But you have to be willing to make the tough decisions and then live with the consequences. It's easier to do so when you're the owner, because you can show up the next day.
You just have to make sure that your decision-making is consistent and good and has a strong process behind it and is supporting the franchise in the present and the future. I learned that if you're going to aspire to be in a leadership position, you just have to have the backbone and the thick skin to do what you think is right despite the high winds of negativity, pressure or disappointment that others are going to get when you make those tough calls one way or the other. The Boss talked about that a lot.
MLB.com: How does Hal Steinbrenner differ most from George as a boss?
Cashman: The Boss was very emotional and reactionary, and Hal is very practical and patient. They're both hungry to win, without a doubt, but their methods of operation are completely different that way. George would make extremely emotional decisions that at times could work for us and at times would sabotage a certain trajectory we might be on because of impatience.
That's when a Doug Drabek would wind up in Pittsburgh, Freddy McGriff would wind up in Toronto or Jay Buhner would wind up in Seattle. We needed a short-term fix at some long-term interest, and it was something you would regret later. Hal is very methodical and very practical; his dad was different. They're both successful in their own right and they both can have success.
MLB.com: The 1998 team wins 114 regular-season games, wins the World Series and people call it the greatest team ever. Yet before the '99 season, you trade David Wells for Roger Clemens. Was there a sense of trying to even outdo the '98 team going into '99?

Cashman: You have to always be open-minded to remake yourself and somehow improve. That '98 team was special; everything went our way. People were dedicated and committed to each other. Lessons learned from '96 -- after we won in '96, we brought almost the same team back except for John Wetteland; he left as a free agent and so Mariano Rivera became the closer. We mustered a Wild Card and a first-round knockout in '97 with essentially the same team. That team did not jell like it did the previous year. We had in-fighting. It was the Three Musketeers in '96 -- all for one, one for all -- and in '97, it was completely different, even though it was almost entirely the same personnel. I learned from that.
In '98, we had a magical carpet ride; 125 wins, 50 losses and something just dramatic and special. That winter, I noticed David Wells, who was one of the special participants in the '98 season, he was partying all winter time, putting on weight, he was out partying with Tom Arnold and flying all over the place; there was a little different vibe of, 'Will we be as committed going into next year in '99 as we were in '98?' Here was this big, John Wayne-type in Roger Clemens who had accomplished everything in the game -- Cy Young Awards, All-Stars, one of the best pitchers of his generation, big workout fiend -- but the only thing he hadn't won is a championship. I knew that man was going to be motivated to all end.
We had a lot of discussions internally, and if we could find the right deal, we felt that going forward, Roger would be a huge impact on us. We made the tough decisions and that was not an easy one, but we felt it was better as we moved forward, that would allow us to get closer to another championship -- or championships -- and it played out that way, to be quite honest. It was a tough call, but I think it was the right call.

MLB.com: You had never been a seller at the Trade Deadline before last year, when you traded away four players. What was that experience like for you, going through that for the first time?
Cashman: High-stakes poker, I guess, so to speak. You never want to be in a position to have to do that, but when you're in those positons, you need to make the right decisions for your franchise. As tough a decision as that was, we made the absolute right call for this franchise's future. It's not part of the Steinbrenner DNA to quit or give up, but what is, I think, in anybody's DNA is to make good, sound business decisions.
I think there was that fork in the road that we faced. Do we want to double down on a roster that hasn't performed up to expectations? Or do we want to call it what it is -- recognize that it's very important right now, there are some high winds, a storm brewing out there and we better tack our sails and change direction and change course or we could sink. I think we made the prudent business decision for the franchise and our fan base, and we will be rewarded for that.
MLB.com: The current youth movement has gotten a lot of attention. Has the fan base handled it better than you thought it might?
Cashman: No. I feel I have a pretty good pulse on what the fans' interests are. I think the fans were hungry for this; they needed this, they wanted this and they got it. I think they're responding in kind. I think they're excited about a lot of the youngsters and they really are out with the old and in with the new.
MLB.com: There has been a lot of talk over the years about the Yankees' inability to develop young starting pitchers. Do you think that's a fair criticism? 
Cashman: Yeah. It's a fact. I think part of the process has been certainly where we draft. Because we've had a lot of success, we've not been allowed to tank and go off the board and therefore get access to some of the high-end stuff that plays out to be impactful. Part of it is we can't get out of our own way because we don't have the patience to let guys finish off their development, because if you possess some unique ability that stands out above everybody else -- whether it was Joba Chamberlain, Ian Kennedy, now [Luis] Severino and before that [Bryan] Mitchell and Shane Greene -- we're pulling them up before their development is finished.
Teams like Tampa Bay, for instance, they're going to wait until they have their four pitches down and their innings limits are all exceeded at the Minor League level; they're very disciplined in that approach as they finish off their starters. For us, if I'm looking at my owner and he says, "What's our best team we can take north?" Well, "We could take this guy; he's not necessarily 100 percent finished off, but we can stick him in our 'pen. He can be in the back end of our rotation, because he's better than some of the guys we already have," and then you cut corners, so I think that probably plays a role in it. And sometimes we don't make the right decisions, either, when we're making Draft selections and signings and stuff like that. On top of it all, playing in New York is a lot different than playing anywhere else. 

MLB.com: With this crop of young guys you have now -- pitchers and position players -- do you have to limit that temptation of bringing them up too soon? Do you need to let them finish off their development in the Minors before you do?
Cashman: If you can. It's always in your best interest to have that safe bet, but again, we're trying to win at the same time. That's the balancing act. I'm giving the audience a chance to walk into our meetings. Those are debates we have constantly. It's development vs. the need to compete on a daily basis in New York. "It's OK if we lose now so we can win later" -- that's not something that, unfortunately, we're really allowed to do. We have to try to win on a daily basis. That's why you're seeing our record; we've had winning seasons now for I don't know how many years, because we're not allowed to "cry uncle" and save it for another day. If the guy is better than what we already have and he gives us a better chance to win, most of the time, that player is going to wind up on our 25-man roster ahead of schedule, because that's just the way we go about our business.
MLB.com: After the Cubs won last year, people already started reserving Theo Epstein's place in Cooperstown. Do you ever think about the Hall of Fame when it comes to yourself?
Cashman: No, I don't. But I do know Theo's getting there without question. He's obviously had a tremendous run. I told Goose [Gossage], "I hope Theo's plaque lines up right next to you; that Ivy League GM." (laughs)
MLB.com: After the Chris Sale trade, you called the Red Sox the "Golden State Warriors of baseball." Predictably, we all put that on the back page the next day. Are you entertained by that kind of stuff? Do you think about how your words are going to play out in the papers and online before you say them?
Cashman: Absolutely.
MLB.com: You came to that session with us with that Golden State Warriors thing ready to fire.
Cashman: When that trade was consummated, that was the first thing I thought about, which was, "Wow, look at what they've done." I know how it's going to play out for them. Listen, Steve Kerr does a great job managing that team -- oh, I mean John Farrell. It's a lot of talent and with talent comes pressure to perform. I think Dave Dombrowski has done everything he possibly can to provide that city with a world championship team. They've got 162 games to show it.
MLB.com: The postseason was such a given for you guys for so many years; you made the playoffs in each of your first 10 seasons as GM and 14 of the first 15. But you've had one playoff game -- a Wild Card loss to the Astros -- over the past four seasons. How tough has this period been for you given what you went through for the first 15 years as GM?
Cashman: You want to win, but you've got to be realistic at the same time about where you are and what you are. All those teams had a chance if everything played out well. The year that we ended up in the Wild Card against Houston, I think if you were looking at us in late-July or early-August, we were considered potential, "This is the team that's going to represent the American League in the World Series." Mark Teixeira broke his leg, Tanaka got hurt, Eovaldi got hurt; we didn't make any trades at the Deadline because we were the best team through July. Then Toronto went gangbusters and really improved their club to their credit; we stood pat and then we got hurt in August and the whole dynamic of our club changed.
It didn't play out the way we expected it. I thought last year's team had a chance, but then the middle of our lineup didn't perform at all; Alex disappeared and didn't play the way he had the previous year and Tex again was battling injuries. The productive 3-4 that helped us the previous year massively didn't contribute anywhere close to that last year, and it changed the dynamic. What we're trying to do as we move forward is hopefully we'll have a much younger, more diversified group so that we're in a position to not put all our eggs in certain baskets and live and die by it. 

MLB.com: How do you view the state of the American League East right now and going forward?
Cashman: Up for grabs. The American League East is the best division in baseball -- I don't even think it's close. The Red Sox and Toronto and Baltimore just because they were there, those teams are the teams to beat. All three made the playoffs last year and I know us and Tampa Bay are trying to fight our way back into it. We look forward to competing with those guys.