Shapiro had a hand in building all three Indians teams that have appeared in the World Series since 1995, including last year's Cleveland squad that beat his Toronto club in the ALCS. Now, as president and CEO, he's trying to help guide the Blue Jays back to the Fall Classic for the first time since 1993, while also mapping out changes to Rogers Centre, hoping to transform the multipurpose stadium into what he calls "a baseball ballpark."
Shapiro recently sat down with MLB.com in his Rogers Centre office for an episode of the Executive Access podcast, discussing his start in baseball, his impressive tree of executives, Josh Donaldson's future and "Moneyball" vs. "Major League."
Here are some highlights from the conversation, but you can listen to the entire interview here.
MLB.com: How did you get your first job in baseball?
Mark Shapiro: A lot of people know that my dad, back in the '80s, was an agent; he happened into that by helping Brooks Robinson out of bankruptcy. I was working for my first job out of college in Southern California for a big real estate developer, and I flew out to Phoenix to spend a couple days with my dad as he toured camps and saw all his players. From that time, I met with Joe McIlvaine, Jim Beattie, John Hart and Dan O'Dowd.
I was unhappy at my first job, which is not unusual, and of course like every 22-year-old kid, I wanted to work in baseball. My dad said, "You don't want to be an agent," and didn't even open that avenue to me. I wrote 26 -- there weren't 30, there were 26 teams -- resumes and cover letters and sent them out. I didn't hear back from many. About eight months after I sent the letters, I got a call from Dan O'Dowd, who was the assistant GM with the Indians. The Indians were the worst team in all of baseball; they lost  games in 1991.
It was a generic entry-level job with no title; just assistant baseball ops and a pay cut in Cleveland. The movie "Major League" was pretty much all anyone knew it for -- and I couldn't wait. It was especially more about John Hart and Dan O'Dowd, their vision for the organization with a new stadium coming two years down the line. They were just people that I wanted to work for and work with. I drove a U-Haul truck into Cleveland in January 1992, and took that job, really buying into people more than anything else.
MLB.com: What did you learn most working under them?
Shapiro: That's easy. From John, empowerment. For me to have been a 25-year-old guy that they turned the player development system over to as a farm director, for me to walk into John's office at 25 years old and say, "I want to develop an individual player plan system for every player and want to think about developing players holistically, mentally, physically and fundamentally; I'm going to do it respectfully, I'm going to earn respect," and for John to say, "Hey, you're a guy; I've got your back. I believe in you." For him to empower me at the level he did, I didn't fully appreciate it at that age. Now I look back at the young guys in our office and think, "Holy cow." How much he believed in me, the power of that belief is immeasurable. I've tried to pay that forward.
MLB.com: On the pay-it-forward front, I did these podcasts with all 30 GMs during Spring Training, and I feel like I asked maybe one-third of them what they learned working under you. You have a very impressive tree of guys who are major executives around the game: Chris Antonetti, Mike Chernoff, Ross Atkins, Derek Falvey, Mike Hazen, Neal Huntington and David Stearns. What's it like for you to see all of these guys who worked under you go on to these kinds of levels?
Shapiro: We're all in this to win a World Series, but I have kind of believed more that the process leads to the result. I've always viewed making it a great place to work, investing in developing people and helping them to be the best they can be and helping them realize their goals and get their dreams to be part of the job. I get a tremendous -- maybe the most -- fulfillment professionally out of seeing those people do great things and achieve great things.
I celebrate with them when they celebrate, I bleed with them when they bleed. When we play them, I still want to beat them. It's just like a little brother you play; that's how I felt when we played Cleveland last year in the playoffs. But I love those guys, I care about them and I'm pulling for them. In some ways, I played some small role in them getting the opportunities they've got, but they played just as big -- if not a bigger -- role in helping me grow. A big part of that is those guys challenging us to continue to learn and grow.
A learning environment, a learning culture, comes from getting really bright and talented people in and then turning them loose, empowering them to help make us better. Creating that understanding that that's what we're about, whether it be the intern, directors or the GM, we want to create an environment where everybody is looking to get the decisions right, grow and get better as an organization all the time. Those guys, while I was around them, challenged me and helped me grow and learn to stay relevant. It's now been over 25 years, so I have to stay relevant.
MLB.com: You started with the Indians as a baseball operations assistant in the early '90s, moved up through the ranks as farm director, you ran the Latin American operations, were the vice president of baseball operations -- a lot of job titles. Was GM always the ultimate goal for you?
Shapiro: Great question. I never -- this is the honest answer -- I never felt like I had to achieve a certain level or a certain job to be successful or have arrived. I felt that leading was extremely important to me; I enjoy leading people, I enjoy helping people come together to achieve something great. I felt that continuing to grow, develop, learn and be challenged was important.
What the different jobs -- less the titles, but the different roles and jobs -- did for me was never caused me to stagnate, always allowed me to grow and learn and continue to get better. Always challenged me that there was a new set of responsibilities that I had to adapt to, including the business side, when I became team president over there. That progression really fulfilled me and satisfied me from that perspective. I had to continue to learn something new and I had to continue to earn respect from people and had a different platform to lead.
MLB.com: You were a character in the movie Moneyball. I'm sure you've been asked your opinion on the movie and the actor who played you a hundred times, so I'll ask you a different question: What's the better baseball movie: "Moneyball" or "Major League"?
Shapiro: "Major League" was more entertaining to me, because it didn't try to be true to life. "Moneyball" was actually interesting. ... I always say it's probably like the emergency room doctors and [the television show] "ER" or legal dramas for lawyers. "Moneyball" tried to take three or four years and condense them into 90 minutes. To do that, you have to take a lot of liberties with what actually happened and condense it, so I find myself distracted by the things that aren't accurate or the things that didn't actually happen -- or the fact that I wasn't even a GM yet when I was being portrayed as a GM. I get distracted by that, whereas with "Major League," you're just laughing.
MLB.com: After spending 24 years with the Indians, how difficult of a decision was it for you to leave for the Blue Jays?
Shapiro: It's difficult, largely because of the people that you are about and you're tied to. It took two things: a compelling situation, which I feel like Toronto was, because it had so many unique attributes of things that were important to me. Two, it took the support of my family; their willingness to consider an adventure in leaving a place they had been their whole lives with me. Those two things. But it wasn't like I was out of work and it wasn't like there weren't things along the way that we also considered elsewhere; this just felt like the right opportunity at the right time.
MLB.com: After you took the job with Toronto, the Indians had you catch ceremonial first pitches from both of your kids. What did that mean to you to be out there with them?
Shapiro: Man, I'm getting emotional thinking about that. Family and baseball are the only things in my life. I'm not a hobby guy; I don't play golf, I don't play cards, I don't go on ridiculous vacations. I've got baseball, my job and my work, and my family. That's it. I don't tend to be someone that spends a lot of time reflecting; I just want to keep moving forward. That was a day and a moment of reflection; a "Holy cow, I can't believe it's been 24 years since I walked up the staircase at Gate A in Municipal Stadium in Cleveland to John Hart's office with the space heater, the plastic plant and the missing ceiling tiles" [moment.]
MLB.com: It sounds like "Major League."
Shapiro: It really wasn't far from it at Municipal Stadium. Reflecting on that, those 24 years, it was a long time.
MLB.com: How difficult is it to endure the type of start to a season like your team had this year?
Shapiro: Even in your 26th year, it doesn't get easier when you lose. The day you wake up and you feel as good getting out of bed when you lose as you did when you win, you're probably in the wrong line of work and it's time to move on to something else. What I always try to do is turn that to fuel, motivation and desire, to focus on situations. Focus on what you can control. The most important thing is to take that bitterness you feel when you lose a game and say, "OK, what can I do to be productive with that? How can we win? How can we get better? Where are the opportunities?"
Sometimes what fans don't think about is that the Major League team is just the tip of the sword. Underneath it, you've got where the bulk of the work is being done. Whether it's the Draft, the player development system, international, Latin America -- baseball allows you so many other things you can focus on that are important to take care of to ensure that if you want to have a sustainable championship team, you better be paying attention to the details. All of them, up and down the organization.
MLB.com: How do you assess your farm system now?
Shapiro: Much better than it was two years ago. Probably in the upper half, maybe closing in on the upper third -- but not where it needs to be. I think we're really excited about what's happening at [high Class A], at Dunedin, the Florida State League and below. Still concerned about Double-A and Triple-A, the depth of prospects there. I look at Dunedin, Lansing and our three short-season teams, and to have all three short-season teams in [the] postseason and well above .500 with talented players, to look at our left side of the infield in Dunedin, to look at Bo Bichette and Vladdy Guerrero Jr. and some of the other players there.
To know what it takes from having seen it in Cleveland; you don't just need two guys, you need waves of guys. And behind them, you need another wave of guys. I feel like that's coming. It's probably two to four years away that it's going to get here, but when it comes, what we've continued to execute on whether it's [assistant GM] Andrew Tinnish leading us in international, we've got waves of guys coming. I'm encouraged by that.
MLB.com: We've seen teams essentially rebuild their farm systems -- or at least the upper echelons of their farm systems -- with one or two big trades. Josh Donaldson is going to be a popular topic for the next year; he has a year left on his contract. When you have a guy like that who is approaching his final year before free agency, do you have to consider all options going into this winter and next season?
Shapiro: You walk through all alternatives at every decision-making juncture. In this situation, the desire to win and to continue to give a relatively new fan base -- because a lot of fans that are coming are new fans -- a reason to cheer and to come to the ballpark is probably more important than just maybe pushing the express button on how to regenerate and reinvigorate the farm system. We've tried to balance that by understanding and doing a lot of that work at the lower levels.
The next juncture to look at that will be the offseason. The next juncture after that will be the Trade Deadline. When we think that we no longer have the opportunity to build a contending team, whoever is there, we're going to have to consider, do we trade those guys? Not JD specifically, but whoever it is, we'll have to consider can we do things that help us when we're able to be a contender again?
MLB.com: You traded popular players away in Cleveland -- Roberto Alomar and CC Sabathia both come to mind. How tough is it to make those decisions when you know that in the immediacy of them, they're not going to be very popular with your fan base?
Shapiro: By the way, that list is a lot longer than that. Bartolo Colon, Cliff Lee, it goes on and on. There may not be a tougher thing for a leader of a baseball organization, but the reality is that your job is to have one eye on today and one eye on the future. You have to understand that every constituency that is invested in what you do, whether it be your internal -- players, coaching staff -- or the people that work on the business side of the organization, they're only concerned with right now, this moment. Your fans are only concerned with this moment and winning, yet you're one eye on the future and the rest of baseball operations is one eye on the future.
It may sometimes lead you to make a decision that disappoints people that are focused on right now. There is a toughness that is required to do these jobs; that you know you're making the right decision; you're confident in that, you believe in it and you have the strength to articulate that even though you know it's unpopular. If you're concerned with being popular and being liked, these probably aren't the right jobs for you. I've always felt like you're trying to help provide a winner to the people that care, but you want to be right in the end, not along the way.
MLB.com: You once said you don't do this job to be mediocre. Will anything short of a World Series title for the Blue Jays make this a successful run for you here in Toronto?
Shapiro: I think so, yeah. I think as I've aged, creating an organization where 500 people enjoy working, are fulfilled, are challenged, get better, grow and build a sustainable championship organization … there's so much randomness when you get into the postseason. To strictly base all of your success on whether or not you win a World Series, I think you're probably setting yourself up for a pretty fragile existence.
Once we have elevated process here, put people in place and in a structure that there is incredible work being done everywhere and an incredible culture where people are driven to get better and challenging each other to get better, I think the results will follow that. I want us to be in position to win the World Series every year; short of that, it will be a failure to me. Whether or not we do it, I'm not sure I'll judge success or failure strictly based on that.