Yankees assistant general manager Michael Fishman has always loved baseball, so when he realized there was an opportunity to use his number-crunching skills to pursue a career within the game, he made it his mission to make that happen.

A trip to the 2004 Winter Meetings resulted in an interview with the Athletics, but he wound up getting hired by the Yankees months later, beginning a journey that has lasted nearly 18 years.

MLB.com’s Mark Feinsand sat down with Fishman during the season to discuss his entry into the game, what he’s learned from Brian Cashman, why he succeeded at fantasy surfing and much more in the latest edition of Executive Access.

This interview has been edited for length and clarity.

MLB.com: You grew up in Fairfield, Conn. What was your favorite team?

Fishman: I grew up as a Mets fan, actually. That changed very quickly when I was hired by the Yankees. I was a huge baseball fan growing up; from 6 years old on, I was obsessed with the game. I loved watching and loved following all teams. I was a baseball fan.

MLB.com: You were a Strat-O-Matic enthusiast as a kid, and I’ve read that you used to write handwritten reports on every player in baseball. What was it about the statistical side of baseball that interested you so much?

Fishman: Everybody's equal at rolling the dice, but where I excelled in the game was calculating the probabilities. Each player had a card with the chances of getting each result -- home run, single and so on -- and I would calculate the probability of getting each result on the card. I started to develop my own system on how to value the card, sort of a wOBA-like formula where I arbitrarily came up with my own scores for how much a home run is worth, how much a double is worth. Then I created the value of the card based on the probability of each result and my guessed value of what each thing was worth.

I used that to play the game from when I was 7 or 8 years old, just trying to be as good at the game as I could. I was maximizing the chances of success through probability.

MLB.com: You graduated from Yale in 2001 with a degree in mathematics. What did you envision your career path to look like when you graduated?

Fishman: I always wanted a career in baseball. That was my dream from a young age, but in high school and college, it just wasn’t realistic. There weren't many jobs doing statistical analysis in baseball at that point in time, so I got a job outside of baseball.

MLB.com: That job was as an actuarial associate with AXA Equitable Life Insurance. Did you enjoy that line of work?

Fishman: It was a job using my statistical skills, but not to the subject that I was interested in, which was baseball. I played fantasy sports -- fantasy baseball, football and basketball -- competitively. I did some national challenges, won some national challenges with thousands of people on the fantasy baseball side. I was pretty obsessed with that stuff.

MLB.com: You sent letters to all 30 teams, having prepared two projects on how in-game moves affect win probability and on relief pitcher valuation. You had several teams ask if you were interested in an internship, but you passed. How committed were you to finding a job in baseball?

Fishman: I wasn't committed to the big money in the job; I was willing to take a sacrifice, but I was looking for a full-time job. I wasn't looking to just go start with an internship, which makes it a little harder to break in. I sent these sample projects out to every team and got some rejection letters and some interest in having conversations. At that point, I was focused on how to get a full-time job in baseball.

MLB.com: Those of us who attend the Winter Meetings every year see the hundreds of college-age kids who are scurrying around looking for jobs. You were one of those kids in 2004. What was that experience like for you?

Fishman: It was interesting. I was trying to just get to know as many people in the game as possible and make connections. I had the opportunity there to interview with the A's for a position; I had sent a sample project to Billy Beane that he had responded to that led to a job interview at the Winter Meetings. I saw other people who were in a similar spot to me, looking to break into the game, so you had to be aggressive trying to make connections.

MLB.com: I would imagine that after “Moneyball” came out, Billy got hundreds of similar letters from people wanting to work in baseball. Even though he didn’t hire you, was it encouraging that he thought enough of you to bring you in for an interview?

Fishman: That definitely meant something. I finished as a runner-up for that position, but I was able to use him as a reference on my resume afterwards, which definitely carried some weight.

MLB.com: What ever happened to the guy who got the job ahead of you?

Fishman: It was [Giants president of baseball operations] Farhan [Zaidi].

MLB.com: You met with Brian Cashman a year later on Billy’s recommendation. He hired you a week later, in July 2005, as a baseball operations analyst. Was there a bit of risk involved with taking such a leap from your prior career?

Fishman: It was definitely a risk, but I was committed to it. I wanted to work in baseball and make the associated sacrifices that came with working in baseball. Knowing that this is something I was going to enjoy doing, I knew I was going to spend more time at my job than anything else, so I wanted to have that time I'm spending being something that I was going to enjoy. Baseball was always my passion.

MLB.com: A year and a half later, you were promoted to be the Yankees’ first director of quantitative research. Analytics departments were relatively few and far between back then; what was it like being on the ground floor in that area?

Fishman: It was definitely an opportunity to do things with my vision, build things how I felt was best. There was no road map at that point in time. I quickly realized in my first year as an analyst that there was just so much to do and not enough time to do everything. I was fortunate when I had the opportunity to become the director of quantitative analysis to expand the department, hire more people and really build things out to another level.

MLB.com: You oversaw all statistical research projects, providing information, recommendations and advance scouting reports to the baseball operations department and coaching staff. Was it at all uncomfortable trying to convince lifelong baseball people like Joe Torre that this information was useful?

Fishman: Early on, there were definitely challenges. Anything new is always going to have a certain amount of pushback. I was fortunate that I had support from the front office, from Brian Cashman, who helped me along in terms of pushing some of the initiatives. There were definitely challenges early on, and not everything was bought into the first time around. Some things took longer than others and some things were able to make more of an impact early on. It was sort of case-by-case.

MLB.com: In my book with Bryan Hoch, “Mission 27,” Cashman said that your recommendation of trading for Nick Swisher was a big factor in his trust in you, earning you a seat at the table. Was that when you felt you became a real voice in the front office?

Fishman: It's always difficult to go out and acquire somebody who's got a contract, owed a large amount of money moving forward and is coming off a bad year. Why are you paying for somebody who had that performance? It was really understanding the underlying reasons why he was a better player than he had shown the year before and was more like his history prior to his year with the White Sox and betting on that. When there's success with that, it definitely matters.

MLB.com: What was the 2009 championship run like for you?

Fishman: It was amazing. That's what we're here for. That's my goal and the goal of everyone working here -- to win the World Series. It was a great feeling, not just for myself, but for everybody involved in the organization, from the players, to the coaches, to the front office, to the scouts, to player development -- everybody who has ever been a part of it. It was a feeling of pride and accomplishment.

MLB.com: What has been the biggest change in the way analytics are used from the time you broke in with the Yankees in 2005 to now?

Fishman: One is that there's so much more available now, so there are challenges of how to manage the amount of data and how to tackle the number of projects that are available and can be done with the data you have. There’s also more demand for it now, so there are more people you have to get it to.

MLB.com: Do you get frustrated by the narrative that the analytics department is making every decision for the club, including making out the lineup for each game?

Fishman: It’s really not the case. We provide all the tools to make decisions, but the analysts are not making the decisions. [Yankees manager Aaron] Boone will have all the information that we provide, then it’s his job to use what he's seeing on the field combined with the data we provide him and the tools that we provide him to make whatever the best decisions are.

MLB.com: One of the biggest challenges seems to be how to deliver information to players and coaches. Compiling the data is one thing; is relaying it to players and coaches in a digestible way the bigger issue?

Fishman: We've essentially gotten to the point where we have analysts embedded in each department -- whether it’s part of the Major League coaching staff or an analyst with each of our affiliates -- and it's kind of their job to go through that process. They have their own challenges within that, but also leaning on the coaches, who are definitely more understanding of the analytics now than maybe some coaches of the past.

It’s a combination of the coaches knowing each of their players as well as the analysts understanding each player individually and what the right way is to communicate with that individual.

MLB.com: What is the biggest thing you have learned working with Brian Cashman?

Fishman: I have been fortunate to get to learn from him with all his experience; he’s the most experienced GM in the game. He's been through every situation before, so I get to see how he handles any situation. He runs to any situation. If there's a conflict, he's going to make sure it's addressed right away and let nothing linger. He’s not afraid of difficult conversations. Just seeing the open-mindedness and the way he evolves, he’s always seeking higher ground and how we can do things better.

MLB.com: You were part of the group that flew to California to recruit Gerrit Cole. What is it like trying to recruit a big free agent?

Fishman: It's a high-stakes exercise when you're trying to get the top player out there and you know it's going to cost top dollar to get him. But you're ultimately trying to show what the organization can offer. When we met with him, he definitely spent the time with us to get to know what the Yankees were all about. He had his questions prepared of everything he wanted to know about us, so we were trying to provide information to him, let him know what we're about and help him make whatever decision was best for him -- and hoping that it was us.

MLB.com: As a numbers guy, do you believe in clutch?

Fishman: I believe in clutch, but as a numbers guy, it's very difficult to measure.

MLB.com: Is it frustrating when there’s something you can’t measure? Whether it’s intangibles, makeup or the ability to slow down your heartbeat, do you have to accept that there are some things you can’t spit out numbers for?

Fishman: You want to be able to measure everything, but you recognize you can't. There are some things that are part of the equation, part of what makes players good, that you can't measure, so you have to accept that there are some things you can't measure. You can't have a full valuation of everything.

MLB.com: You saw the excitement created by the Yankees’ World Series win in 2009. Not that a 13-year drought measures with the ones we’ve seen in Boston, Chicago and Cleveland, but what would another title mean to the city and the fan base?

Fishman: It would mean everything. That's what we’re trying to do; it's been too long. Ultimately, that's why we're working here. That's what our goal is. I think that the city's definitely ready for it.