Media stories and analysis has become a regular point of focus for Keith Olbermann on his Countdown podcast. On his latest episode, Olbermann took listeners down memory lane to explain how he wound up talking politics on television and how he first decided that he couldn’t do it anymore.

While he had joined NBC months earlier, it was Bill Clinton’s affair with Monica Lewinsky that changed the trajectory of his role there. Olbermann explained that he had been doing some work for both the fledgling news network, hosting a general interest show, and working on NBC’s coverage of Major League Baseball.

Coverage of Clinton and Lewinsky became the bulk of his show every night, drawing tremendous ratings success. MSNBC made Olbermann the anchor of its coverage of the 1998 State of the Union Address. He hosted a pre-speech show and a show that followed NBC’s analysis. During that “postgame show,” Olbermann says an NBC News executive delivered big news to him.

“The speech did in 0.8. Brokaw and Russert on the wrap up did an 0.6. Since 11:00, you’ve been doing a 1.7,” Olbermann says he was told. “You have had three times the audience of Tom Brokaw, three times the audience of the old man himself. This isn’t just people crossing over from NBC to watch more. This is people watching the speech, turning off the old man, then turning back at 11 to watch you.”

He also found out that the AP had used a joke he told on that postgame show in its official recap of the State of the Union Address. All of the success being tied to a presidential sex scandal made Olbermann uneasy.

“I had this sudden horrible feeling that the usually slow to decide American viewing public had instantly concluded that for some reason, elusive even to me, they really like to hear me talk about the whereabouts of the president’s penis.”

Olbermann says it was not long after that that NBC News executives came to him with the idea of creating a nightly show all about the scandal. In order to entice him to give up a planned vacation and commit to the show, Olbermann says he was offered the chance to anchor NBC Nightly News on multiple occasions.

The show eventually launched. It was a ratings success for MSNBC, something Olbermann says he did his best to reverse.

“For months. I mocked the story. The ratings went up,” he said. “I tried to quit the show. The ratings went up. I gave a speech insulting the network for covering the story 24/7. The ratings went up. Fox Sports approached me and offered me five times what NBC was paying me to go out to LA to do their sportscast. LA., which was kind of near Hawaii, nowhere near the Clinton-Lewinsky story. And the ratings went up.”

The network’s dedication to the Clinton/Lewinsky scandal is what eventually drove Olbermann back to sports. It was seeing an NBC News promo for Jane Pauley’s interview with another woman accusing the former president of an extramarital affair that had him call his agent to learn more about FOX Sports’s offer.

FOX News has had its share of struggles with conservative pundits this year. Plenty of voices that used to only praise the network turned on it following the firing of Tucker Carlson. On Wednesday morning though, Tony Katz, a prominent conservative voice in Indiana, was defending one of FOX’s high profile talents.

Donald Trump took to Truth Social on Tuesday night to complain that FOX’s Kayleigh McEnany deliberately shared poll numbers that made his lead over Florida Governor Ron DeSantis amongst Republicans look smaller than it actually is.

“Kayleigh McEnany was his press secretary. Kayleigh McEnany was on CNN defending him back in the day,” Katz said Wednesday on WIBC in Indianapolis. “This post is stupid.”

Although he has been a supporter of the former president in the past, Katz said that Trump’s attack on a former staffer that was charged with defending him and his policy is proof that he has no loyalty to anyone but himself.

McEnany served as the White House Press Secretary for the final year of Donald Trump’s term in office. She left the post following the inauguration of Joe Biden in January of 2021. She has been on FOX News since March of that year.

“This is a pathetic move from Trump. Unnecessary,” Katz said. “This is the lashing out of an angry old man who can’t seem to find his pudding cup. And that’s not the way I want to think of him and that’s not the message he wants to move forward! If he wants to get elected, this is ridiculous. I hate the unforced error. I hate it. But he’s so good at it. He can’t figure out how not to do it.”

Sid Rosenberg, WABC Radio’s morning host, emphasized the importance for aspiring broadcasters to remain true to themselves and avoid pretending to be someone they are not. Rosenberg shared this advice while speaking with his former producer Victor Bermudez, who has achieved great success by winning four Emmy Awards for his contributions at Telemundo.

Rosenberg made the remarks during his Tuesday morning show.

“I’ve said this to Marc Malusis at WFAN; his wife once called me and said, ‘Why isn’t Marc having more success at WFAN and I said because he’s trying to be [Mike] Francesa. Don’t be a radio voice; talk like you talk.”

Rosenberg mentioned that throughout his career, he has encountered individuals like Joy Taylor from Fox Sports Radio, who faced tremendous expectations due to her brother, Jason Taylor, being a former NFL player. These individuals had to navigate significant pressure to succeed in the entertainment industry.

“Overnight, she (Taylor) wanted to be the next Barbara Walters,” Rosenberg said. “I just told her to take it easy, slow down and be yourself.”

Rosenberg said he had similar advice for Bermudez, who admittedly struggled to find his identity in the industry due to many factors.

“I’ve had a lot of producers over the years; it’s not easy producing for me, the show ends, and a minute later, I’m asking who’s on tomorrow,” said Rosenberg. “

Bermudez, who served as Rosenberg’s producer at WQAM in Miami, joined Rosenberg with minimal prior on-air experience.

“I had tons of fun working on the Sid Rosenberg Show during my time with you in Miami; I will add that it was life-changing,” said Bermudez. “It changed my life professionally because I came into business trying to be something I was not.”