Olbermann's charm offensive apparently includes his comment to the Times, in which he lavished Skipper with praise: "I had the privilege to spend some time with John Skipper," he said. "His vision and charm were readily apparent, and judging by his leadership, his family name was prophetic."

In the months since the dinner, Olbermann’s representatives have continued looking for possible opportunities for Olbermann at ESPN, the Times reported, citing a senior executive at the network and someone directly involved with Olbermann’s efforts.

If ESPN does give him a shot, Olbermann will be ready: He spent much of the weekend tweeting images from Major League Baseball's spring training.

And he is working with the network in one sense: He appears in the new ESPN short, "Holy Grail: The T206 Honus Wagner," in which he talks about his love of collecting baseball cards and the significance of the Wagner card.