Startup Westport names ESPN chairman Jimmy Pitaro Innovator of the Year

The world has changed immensely since the Entertainment and Sports Programming Network (now almost universally called ESPN) launched in 1978.

When the channel started satellite, was the exciting new technology that enabled an insurance agent, a former New England Whalers communications director and his son to launch a media empire that disrupted all of sports media.

Today, ESPN is one of the most recognizable brands in the Disney portfolio and a dominant force in sports entertainment. Under the leadership of James Pitaro it is working to expand streaming offerings and pioneer entirely new forms of streaming content leveraging other Disney Intellectual Property.

For those efforts, Pitaro was recognized by Startup Westport as the 2024 innovator of the year on April 30. Startup Westport, which fosters relationships between mentors and mentees among Westport residents and businesses to help the town grow into a center for innovation across industries.

To mark the occasion, Mike Greenberg, the host of ESPN’s “Get Up!” show interviewed Pitaro on the stage of The Westport Library about his biography and approach to business.

“You were a kid with a dream,” Greenberg said after Pitaro was introduced. “You’re a kid from Edgemont, New York, Westchester, grew up playing sports, loving the Yankees… who became the chairman of ESPN.  That is achieving your wildest dream job. So, if you were to speak to the mentees in here tonight about how to go about achieving their dream job, how did you get yours?”

Pitaro recalled how leading ESPN was never part of his long-term plans. He decided to go into law after a professor remarked he would make a good lawyer, and that it was one of the first times he had heard that sort of encouragement outside of his love of sports.

His wife’s acting career eventually took him to the West Coast, and he opted to become an in-house counsel rather than work for a firm.

“I made the decision to go work for a music internet company called launch.com,” Pitaro said. “Ultimately that company got bought by Yahoo. I actually did the deal to sell the company to Yahoo and I just stayed on board and moved from legal affairs to business affairs.”

Pitaro told Green that he pushed to become more involved with the business side of things, and he was ultimately asked to take over Yahoo Sports.

“I went from managing 12 people to managing over 1,000 people overnight, and it was a massive stretch for me. But if you work hard and treat people well things have a tendency of taking care of themselves.”

Eventually, Pitaro, who was not looking for a new job at the time was introduced to Bob Iger, the noted CEO of The Walt Disney Company. Pitaro was intimidated by the prospect of meeting with the owner of Yahoo Sport’s primary competitor but eventually pushed away his misgivings and accepted the invitation. He recalled preparing extensively with the help of his wife.

“I went to his house on a Sunday afternoon. It was supposed to be a half-hour, 45-minute meeting,” Pitaro said. “It was four hours.  We hit it off and I walked out of his house thinking I’m in trouble. I really did not want to leave Yahoo and I was now a bit tormented because I wanted to work for this guy.”

“I felt like I could learn a lot from him,” said Pitaro. When he got the offer to move to Disney a couple weeks later it was a difficult choice, but he said he was ultimately glad he accepted the offer. Pitaro was tasked with overseeing the company’s digital division, Disney Interactive, where he said he learned valuable lessons that he has made use of since taking the helm at ESPN in 2018.

“There was no grand plan here,” Pitaro concluded. “The advice I always give younger people is take the job!”