In June 1997, Skipper became senior vice president and general manager of ESPN the Magazine. In October 2005, he was named as executive vice president of content. On January 1, 2012, he became president of ESPN Inc. and co-chairman of Disney Media Networks. In 2017, Skipper's contract with ESPN's parent company, Disney, was extended through 2021. In his time as President, Skipper was noted for negotiating large television rights contracts for sporting events, including a nine-year, $12 billion deal with the National Basketball Association and a $7.3 billion deal for the College Football Playoff, as well as all four tennis Grand Slams and golf’s Masters Tournament. On December 18, 2017, Skipper revealed that he had been struggling with substance addiction, and announced that he would be resigning as president of ESPN in order to focus on treatment. John Skipper told Sports Illustrated that a cocaine extortion attempt led to his ESPN departure. His predecessor George Bodenheimer served as acting chairman of the company during the transition to new leadership. In the wake of Skipper's announcement, the New York Times reported that he "didn’t have a reputation for partying or erratic behavior" among coworkers at ESPN or confidants in his personal life. After his resignation, many current and former ESPN staffers, including Jemele Hill, Michele Steele, and Keith Olbermann, applauded Skipper’s past work and the decision to focus on his personal life.
On May 8, 2018, it was announced that Skipper had been hired as executive chairman of DAZN Group, a British international sports media company. Skipper will operate out of New York City. The company subsequently announced plans to launch its international sports streaming service DAZN in the United States later in the year, anchored by a deal with British promoter Eddie Hearn to hold major boxing events in the U.S. to carry on DAZN. Skipper explained that he wanted the service to eventually be a larger competitor to entities such as ESPN and compete for more significant sports rights, but that they wanted to "build our brand in this country, expose the quality of our technology and start to meet people." Of his personal condition, Skipper added that "I'm in a great place. I am excellent, quite healthy. I think you can tell that. I have a level of acceptance and enthusiasm going forward."
Legacy
Skipper's time as President of ESPN received both praise and criticism. He was admired for his strong support of journalism. The Ringer wrote that “he knew quality” and “spoke a language that editorial people could understand.” He was credited for taking chances on ambitious projects like Grantland, FiveThirtyEight, The Undefeated, and 30 for 30. Sports Illustrated wrote that Skipper made ESPN "gobs of cash... but he also made the network smarter and sharper." Skipper "championed soccer and the NBA, realizing that ESPN, armed with its many affiliates and platforms, could get more out of broadcast rights than any of its competitors could." He was also praised for pushing ESPN to become "more diverse on air and online when it came to both gender and race." During Skipper's tenure ESPN lost nearly 15% of its subscribers and laid off more than 500 employees. Additionally, ESPN's TV ratings declined significantly across the board and the network endured criticism from some quarters over the declining quality of its programming. Skipper's 2014 disregard of eSports as a "real sport", referring to them as a "competition" instead, has been negatively noted by various websites.
