above: Pitaro in his home office with one of his favorite pieces of sports memorabilia, a one-of-a-kind souvenir football adorned with the Masters golf logo.
With innovation, recommendations and customization at the forefront and a focus on personalization,ESPN Chairman Jimmy Pitaro is rapidly transforming sports content consumption and making the network’s mission to “ To Serve Sports Fans. Anytime. Anywhere ” an actual reality.
Like a graceful game of tennis, ESPN Chairman Jimmy Pitaro and I rallied back-and-forth in his office at its Bristol headquarters about topics ranging from his early days as a litigator to becoming one of the most highly respected media executives globally. We discussed the aggressive roadmap he’s built with his team for the sports-broadcasting network, the largest cable networks in the U.S. With the launch of the ESPN+ direct-to-consumer streaming service. and the forthcoming 2025 launch of Flagship, ESPN’s full-scale streaming service is set to transform the industry. With the hotly discussed retirement of Walt Disney Company CEO Bob Iger in 2026, who famously hired Pitaro, the suggestion of succession, while not the subject at hand, most certainly came up.
Samantha Yanks: How did your interest in sports start?
Jimmy Pitaro: For as long as I can remember, I’ve been interested in sports. I was an athlete as a kid, and I played the usual sports, but once I got to junior high school and high school it was football, basketball, baseball, and I loved all of them — but football was the sport that I was best at.
I started to get recruited for football (in) my junior year of high school, and then it really picked up my senior year. I went to Penn State football camp the summer before my senior year, and started to get a little bit more attention. And then I had to decide about whether I wanted to really go for it; meaning, like Division I athletics, or focus on something that was more realistic, like Division I AA or Division 3. And I ultimately went with the latter; those were really the schools that were recruiting me.
Boston College looked at me for a minute. Holy Cross recruited me heavily, but I ultimately decided to just focus on Division I AA. And so, I ended up focusing on the Ivy Leagues, and I chose Cornell. And I literally chose Cornell for football. There was a recruiting coach named Pete Noyes, who is still very active with the school and very involved, but he was really, really kind to my parents during these recruiting visits. I made the decision to go to Cornell primarily based on this one recruiting coach.
SY: Has sports always been a huge part of your life? It sounds like your parents were very involved in the recruiting process.
JP: Yes, sports have been a huge part of my life, always. I grew up in a household where the Yankees were on for 162 games, even while we were having dinner. I mean, the Yankee game started around 7 p.m.
We would sit down as a family for dinner, and if it was baseball season, the Yankees were on in the background. Notre Dame was on every Saturday. You know, I grew up in a Catholic household, and if you’re Catholic and you live in New York, you’re more likely than not a Notre Dame fan, because we don’t have a huge college football program. It is kind of like you cheer for Yankees baseball and Notre Dame football. It’s kind of odd, and interesting.
Even my mom was a huge sports fan. She does not watch the game when the Yankees are on the field because she’s too nervous and she feels like nothing good can happen.
I feel like (that) in … my DNA … since I was three or four years old. And my wife didn’t understand it when she first met me. She didn’t understand the fandom and the level, the degree, the passion and now she gets it. She sees how it’s just a part of my being. My wife sang the national anthem at a Yankees game.
She had a movie come out, and the Yankees asked her to sing the anthem, and I was on the field with my camcorder. This was like, 1999, and I was recording her and then recording the players. I remember my mother-in-law got mad at me because the video that I took was too focused on the players, because I was trying to make it somewhat artistic and capture her, but also the players. I was proud of it, but when I showed it to my mother-in-law, she was not. She didn’t appreciate the video.
SY: Growing up in a household where sports were center stage, and then being an athlete yourself, when did it become something that you wanted
to focus your career on?
JP: That’s a good question. Probably not until I got to law school. When I was in law school, I heard about a sports law class, and I think that was the first time I said to myself, “OK, maybe I can combine both worlds.” So, let me back up a bit: I failed as an athlete in college, and so that was a wake-up call for me, and I decided I needed to figure out what I was going to do with my life.
SY: It’s a powerful realization, I am sure.
JP: That was my plan, but it didn’t really play out that way. I graduated from law school and went straight into litigation, thinking that somehow, I’d be able to do litigation around the sports industry. But that’s hard, and most of the folks who are involved there are very senior. You must really work your way up, and you also must be part of a law firm that specializes in that. I just didn’t have it together enough to find the right law firm to chart a path to litigating sports cases.
It just didn’t happen. And as a result, I just took a job at a litigation firm. By the way, I thought that litigation was like sports, right? If I was going to be a professional athlete, at least I would be able to compete in the courtroom.
SY:And did the vision play out as you planned?
JP: Definitely not. I started to litigate, and I hated it. I just hated it. I did it for a couple of years, and I was about 24 years old, and I was up against folks in their fifties, and it was really challenging.
I learned a ton, and I feel like it helped make me who I am today, but it wasn’t for me. So, I decided to leave litigation and go into transactional work, which changed my life.
SY: When in your journey through law did you get the media bug? Personally, I have always had a passion for our industry, so I am always interested in how those who are super successful, like yourself, charted their path. Often it is not a traditional trajectory.
JP: Yeah, my path is a gigantic zigzag. I was watching an Eagles documentary on Netflix, and Joe Walsh, the guitarist and singer-songwriter — from the Eagles band, not the Eagles football team — was being interviewed. He said, “You know, living my life, I always felt like it was like this complete and total mess, this cacophony. And now when I look back, it seems to me to be a beautiful symphony.” Similarly, for me, there was no linear path leading to ESPN. It was very, very messy.
But to answer your question, it was when I met my wife (Jean Louisa Kelly), that I really had not had much interest or exposure to the media industry. She had been an actress since she was a little girl, and I got very involved in her career. I immersed myself in it and learned a ton. I was helpful to her as a lawyer a tiny bit, but she had a whole team representing her, so she didn’t need me. But I was fascinated by what she did.
So, I started to read the trades and just really educate myself. And then it was her career that took us to the West Coast, which was the trigger for me quitting my job in New York. She got on a television show that was shooting in Vancouver, and I walked into my law firm and resigned, we were married at this point, and we moved to Vancouver for her career.
SY: I hate to suggest a spoiler alert, but I’m guessing things did not go as swimmingly as planned.
JP: Yeah, then her show got canceled! You know, we were rookies, we were in our mid-twenties, and we were told that the show was going to “run forever,” so I quit my job.
We sold our charming little apartment in the West Village of Manhattan and moved … And the show: I think she shot nine episodes, and then they canceled it on Halloween in 1999. We put our dog Pags, who was named after Yankees 3B Mike Pagliarulo, in this van that the production crew let us borrow, and drove down to Los Angeles from Vancouver. My wife immediately signed what’s called a talent holding deal with the CBS network. It was a multiyear commitment. So, we were like, OK, L.A. is going to be home now.
So, I started to put my feelers out for a media job, and I decided that I did not want to do television or film because that was her industry. I knew I loved music. So, I went the music route, and I landed a job as an in-house attorney for a music internet company. And that changed my life because that was my first step into media and entertainment, and my first step into technology.
And I loved it; I really loved it. The company had just gone public, and it was thriving. It was music and it was a joy, and I was surrounded by young, smart, energetic people. Then we got caught up in the bubble bursting and were running out of cash, and we made the tough decision to look at potentially selling the company.
We started to engage with large tech firms and, long story short, Yahoo! ended up buying us. I did the deal with an outside firm helping, and then I decided to stay on board with Yahoo. And I did that for a few years as an in-house lawyer/business affairs guy. Then I got the huge break. The guy who was running Yahoo Sports left.
His boss knew me because I had done some deals for him on the music side, but also knew that I was not only an athlete but a huge sports fan. And so, he asked me to lunch one day, and he asked if I would be interested in running Yahoo Sports. I was somewhat incredulous at the time because I was managing twelve people as a lawyer. And so, this was going from managing twelve people doing deals to running an organization of over 1,000 people with front-end engineers, back-end engineers, designers, marketers, sales, every aspect. At the same time, I said, “Well, this is my opportunity.”
SY: I’ve followed your career for some time, and I have to say, going on this journey with you and getting the behind-the-scenes play-by-play is fascinating. So that was the moment, right?
JP: Exactly! That was the moment where I left law, which was a defining moment for me. Truthfully, it was a huge risk because I know the law, and I knew I could practice for the rest of my life and earn a good living.
SY: Right, to be secure and safe but this is the risk many wonder about taking, following your passion.
JP: Yup. And I decided to follow my passion. So, I took the job at Yahoo Sports, and it went well, I immersed myself in it and the guy above me then left. And fast forward, within a couple of years they asked me to run all of Yahoo Media. I went from running Yahoo Sports to now news, finance, entertainment, games and more. I was running the Yahoo Los Angeles office which had thousands and thousands of people. It all happened very quickly for me. And as I looked at the competitive landscape, I would wake up every day saying to myself, we need to beat ESPN.
office including a 2020-2021 Sports Emmy.
SY: In the back of your mind did you think I want to beat them and one day I want to work there? Now you’re here and hit the pinnacle.
JP: No, I can’t tell you that that was the plan. It would seem logical that first I would want to beat ESPN, then join them. But it was just a focus on beating ESPN, the standard, that was it, that was my motivation, and it was everyone’s motivation, and we did it. And that’s, I think, how I initially got Bob Iger’s attention.
Interestingly, Dave Goldberg, who hired me at that music startup earlier in my career, married Sheryl Sandberg, who was the chief operating officer at Facebook. She joined the board of Walt Disney Co. in 2010. As soon as she joined, she called me to say she was unhappy with the Disney interactive leadership, which was one of the five segments at the time. She asked if I would be interested in meeting with Bob Iger. At first, I said no, because things were going so well for me at Yahoo, and I’m a very loyal person. I was on a good path and the thought of leaving when things were going well, when it was all working and clicking, seemed nuts so I politely declined.
A couple of months went by, and she called me back, and she suggested I just take the meeting. So, I went over to Iger’s house on a sunny Sunday afternoon in Los Angeles, and it was supposed to be, I think, at most a one-hour meeting, but it was several hours. I remember leaving his house feeling like I wanted to work for this man. That was the moment I decided to leave Yahoo and join Disney.
SY: For you, growing the ESPN community is key but keeping the core is essential, too. How do you feel that you’re best getting kind of the next consumer and keeping the one that you have engaged within the ESPN ecosystem for some time?
JP: So that’s the challenge. The challenge is to expand your audience and not disrupt your core audience in the process. The way we’re looking at it is we’re running parallel paths. And what I mean by that is we will continue to be available to fans that want to buy or access ESPN in the traditional ways. For example, DirecTV, Comcast, Cox, Charter or Dish.
There are many, many millions of people and households that are quite happy with the value they’re getting from the cable or satellite model. And we’re going to continue to be there. At the same time, we know that there are over 60 million households in this country alone that either have cut the cord or have never subscribed to the traditional linear ecosystem. And that’s a tremendous opportunity for us. If you have 60 million people or households on the sidelines, we feel like we need to give them the opportunity to purchase ESPN in the way they want to purchase ESPN, meaning à la carte.
SY: So, give us a snapshot of what the future of ESPN looks like.
JP: If you want to buy just ESPN, come this time next year, you’ll be able to do that again. If you are very happy with what you’re getting today, meaning the value in that traditional ecosystem and you want more than ESPN, you want almost all sports content, and you want general entertainment and news, we’re going to continue to be there. The bottom line is we want to be everywhere. And ultimately, we’re going to evaluate ourselves based on the total number of households that are subscribing to ESPN.
That cuts across the traditional model and these new models. For example, direct-to-consumer. Then on top of that, it’s accepting the fact that many people in including or especially younger people, are very happy with the YouTube, Instagram and TikTok experiences. We need to be present on those third-party platforms as well, and importantly, present in a way that is not just marketing.
SY: It must be authentic entertainment, real content in real time. When I look at your approach it is innovation, personalization and what is the next-gen going to engage in.
JP: Yes, it’s got to be in the format that younger people are accustomed to or looking for, meaning bite-size, short-form content. We have a team here of over 60 people that do nothing but create content or identify content for our ESPN handles on third-party platforms. We are the No. 1 media brand in the world on TikTok. If you look at our growth on Instagram and on X and on Facebook, it’s great across the board. So that’s the social bucket. Then on top of that is YouTube. And we’re creating content natively for YouTube on a regular basis. So, we do both.
We will take clips from linear television, put it up on YouTube, or we will have a portion of Pat McAfee’s show air live on YouTube, or we will create content specifically for YouTube. So again, the idea is we need to be everywhere. Our mission is to serve the sports fan anytime, anywhere.
There are certain platforms that are more lucrative than others. But from our perspective, if it truly is fan-first, we need to be everywhere and accept the fact that some of these platforms might not be as lucrative as others because you’re sharing the revenue. But that’s OK, because my job is to think brand-first, fan-first, and think long-term.
SY: For you, studio content is a point of differentiation in the sports landscape and sits squarely in the ESPN ecosystem. Is it something that our community really wants?
JP: Great point. It starts with an understanding of ESPN’s DNA. The way I look at it is that ESPN is the place of record. So, when something happens in the sports industry, you better hear it first from us and historically you have. So that’s why people tune into ESPN. They don’t just hear it from us first; they hear it from us reliably.
SY: And, authoritatively, and with charm and charisma, as you have noted.
JP: Exactly. And by the way, with wit and heart and humor. We also have this megaphone that you’re identifying with our studio programming that is really a differentiator for us. When you look at the sports industry in general, who else is covering sports 24/7 across a multitude of networks? No one is.
It’s a huge advantage of ours when we sit down with the leagues to negotiate rights deals. They love the fact that they’re getting all this promotion from ESPN. And if you were to talk to Gary Bettman right now, who’s the commissioner of the NHL, he will tell you that the period, which was over a decade, that he did not have a partnership with ESPN was painful for him and for the league because he was getting less promotion and less amplification.
It’s helpful for us from a league and rights perspective. But it’s also, as I said, part of who we are, which is the place that you turn to when sports happen, when breaking news happens. And that is one of our priorities, quality storytelling and programming. Again, when you tune in to Get Up or First Take or SportsCenter, Pat McAfee, Pardon the Interruption, Around the Horn, when you tune into any of that programming, you’re getting the news, but you’re getting it delivered with charm. And that, to me, is who we are.
SY: Going back a bit: There are a variety of revenue channels for ESPN, part of what you oversaw in your earlier days was gaming at Yahoo Sports. Can we talk a little bit about gaming?
JP: You’re right in that. I have a long history in this space. So going back to Yahoo Sports, their most important asset was fantasy. And we were No. 1 in fantasy, which was a significant source of pride for the team.
When I left Yahoo and joined the Walt Disney Company, I was hired to lead a segment called Disney Interactive, which was one of the five segments: theme parks, movies, television, consumer products and Disney Interactive. Part of the mandate, or my mandate, was games. And when I started in October of 2010, we had just acquired several vertical game studios. The Walt Disney Company was suddenly in the game development business, not just the licensing business where we would grant a company the right to use our intellectual property in their games.
We were now doing that, but also creating our own games, writing the code. We had software developers, hundreds of them, working for us, and you can understand how that happened. For so many years, folks have been talking about the emergence of gaming and the power of games and the next great media frontier. And again, rewinding to 2010, we saw the opportunity, we saw the potential, and so went out and started buying up these game studios. The problem is, it’s a really hard business and also very tough to predict and its resource intensive.
While we had hundreds of engineers, we were competing against enterprises that had thousands, I imagine. And while we had far superior IP, in my mind, we did not have far superior developers. And I had to make the very tough call of exiting most of the vertical game development. Now, just to back up, when Bob Iger hired me, he gave me a very clear mandate, which was get this business to profitability. So going back to my point on there being five verticals, only one of them was losing money, and that was mine, Disney Interactive.
We were losing hundreds of millions of dollars a year. Bob hired me and really wanted me to focus on turning it around financially. I saw an opportunity to consolidate things, cut a lot of what we were doing, and focus on our websites, our apps, our short form video, and the licensing of our IP to game developers. We went from losing hundreds of millions to making hundreds of millions within a three- or four-year period. That was a very pivotal time for the Walt Disney Company to get that business turned around. And I take some pride in that. But it was also very, very challenging. And then in 2014, Iger decided to merge physical consumer products and Disney Interactive together and create one segment. We went from five segments to four at Disney, and he asked me to lead that, which I did for several years. That was another stretch opportunity for me.
I had no consumer products experience, zero. But I learned the business and I liked it. And then in 2017, the person who was running ESPN resigned. And so, Bob then asked me to move to Connecticut. And here I am.
SY: Iger’s name has come up a variety of times in this conversation and his retirement in 2026 is public. Your name has been continually discussed as the heir. Do you speculate? Is that something that you think about? Do you enjoy being asked about it?
JP: I will honestly answer your question. It is not something I enjoy discussing. But I will tell you without any hesitation that I am in my dream job as an athlete and someone who spent years competing against ESPN, then spent years at Bob Iger’s table and really immersing myself in this place. I just love it. I love the culture. I love the people. I love the opportunities in front of us, especially what we’ve talked about already, which is making our networks available direct-to-consumer à la carte, over-the-top. We have a complicated and robust product roadmap and that takes all my attention.
Our new year started on October 1, so when the leadership team and I got together we discussed our upcoming priorities. We have so much to do over the next year, really over the next five years, to be honest with you. We do a five-year plan every year for the Walt Disney Company, and it’s complex. And so that is, and I’m not copping out here. I’m just telling you honestly, that is where 100% of my focus is.
SY: Let’s talk Westport
JP: I absolutely love Westport, and I honestly believe that this will be our last home base. I grew up in Westchester County, it’s not technically New England,
but it might as well be. But I’m a Connecticut and Westport fan. I’m converted.
SY: You’re all in?
JP: I’m all in.
SY: Why Westport?
JP: My wife has a very dear friend Andrea who introduced us in 1994 in Westhampton and lives in Westport. When we would come back from L.A. to visit my wife’s family in Massachusetts or my family in New York, we
would go visit Andrea. And we would always say, “Wow, if either of our careers ever brought us back to the Northeast, this is where we would live.” We would go for visits to Compo Beach and have great meals at quaint little restaurants. Fast-forward to December of 2017. When I started the interview process for the ESPN job, my wife and I said, if this happens and if we move, it’s Westport. So, we had complete clarity. When you add the amazing public school system, the sports, the great theater community, specifically the Westport Playhouse, a place where my wife has performed and a fan of forever, it was perfect.
My kids are both active in the arts community, my daughter was a Staples Player and thrived in that community. My son was, and is, a musician, and so it’s been great for the two of them. My son was also a boxer, and we have this amazing boxing facility run by Rich Dean on the Post Road, who he trained with for years.
SY: And finally, let’s talk location.
JP: We love being near the water. When we first moved, we rented a house for three months near Compo, and we contemplated buying the house that we were renting, but it was just a tad too small. So, we moved inland to Greens Farms and just love it.
We’re less than a mile away from the water. So, yes, that’s it. We’re all in.