Keith Olbermann – $25 Million

For many ’80s kids, Keith Olbermann’s show, Sportcenter, was the go-to place for everything related to sports. He subsequently took up a string of jobs with Fox, CNN, and MSNBC before completing a full circle and coming back to ESPN.

Over the years, neither Keith’s popularity nor his wages waned, and he went on to earn nearly $4 million a year at the peak of his career. After accruing a bank balance of almost $25 million, he has now switched to YouTube for presenting the news while making rare TV appearances.