Olbermann’s expressions of interest included dinner at New York’s Four Seasons Restaurant with John Skipper, ESPN’s president.

“Keith Olbermann, both personally and through a couple people I know, reached out to say, ‘Gee, I would love to have dinner,’ ” Skipper said. “I agreed to dinner with Keith because I assumed he’d be provocative and witty and fun to have dinner with, and he was indeed lots of fun. We talked sports and politics, and we had a nice chat. He is very interesting…

In the months since that dinner, Olbermann’s representatives have campaigned at ESPN for possible opportunities, according to a senior executive at the network and someone directly involved with Olbermann’s efforts. Both people asked not to be identified because they were not authorized to speak publicly about the discussions.