- Forced to resign from ESPN due to a cocaine addiction.
- President of ESPN, Inc. and cochairman, Disney Media Networks (1 January 2012-present).
- In 2021 he founded Meadowlark Media.
- Disdain for UFC and eSports: During his tenure at ESPN, Skipper was a vocal critic of certain emerging sports. He famously refused to broadcast UFC, as he reportedly disliked the sport. He also dismissed eSports as a "competition" rather than a real sport in 2014.
- Champion of Diversity: He is credited with being a major force behind diversifying ESPN's on-air talent. He was a vocal supporter and "protector" of personalities like Jemele Hill, even when their social and political commentary drew public scrutiny.
- The Extortion Plot: While it is known that Skipper resigned due to substance addiction, the specific trigger was a cocaine extortion attempt. He revealed in an interview that someone he had purchased drugs from attempted to extort him, which he felt put his family and the network at risk, leading to his sudden departure in 2017.
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