Olbermann said he had an impromptu "heart-to-heart" at Tuesday's baseball All-Star game with longtime ESPN anchor Chris Berman, who gave him his sports broadcasting start four decades ago as his assistant at their high school radio station in Tarrytown, N.Y.
Olbermann told his former-and-future colleague he put out feelers to the network more than a year earlier partly because he wanted his association with ESPN to be remembered for innovative television, not acrimonious splits.
"It meant something to people," he said of his "SportsCenter" glory days, "and it meant something to us."
Skipper, who joined ESPN the same year Olbermann left, said he spoke to many employees who had worked with the former anchor. He had to make a "calculation" of how much Olbermann's "singular talent" would help the network.
"It's much more about what Keith is going to do than about what people at ESPN have in their memories or previous experiences," Skipper said. "Keith is committed to working through that, and I'm in support of that."
Olbermann served as co-host of NBC's Sunday night NFL pregame show from 2007-09, reuniting with old "SportsCenter" anchor partner Dan Patrick for the last two seasons. He recently added another sports gig, hosting TBS's Major League Baseball postseason studio show.
Olbermann said executives at both networks supported making the two jobs work. He'll take time away from his late-night hosting for his baseball responsibilities this fall.
For now, at least, he's a sports anchor, an ESPN commentator, an employee speaking glowingly about his bosses.
"I could say to you that there were moments when I thought this would never happen and this was not something that was even within the realm of possibility," Olbermann said of reuniting with the folks in Bristol, Conn. "But every time I've made a prediction like that, even internally to myself, I have been completely wrong.
"There is no way to forecast my career path, and I've given up trying."
AP Sports Writer Beth Harris in Los Angeles contributed to this report.