Bill O'Reilly on Brokering a Secret Hostage Release Deal

Two weeks after one phone call, four hostages walked free from Gaza...

A Note from James:

After the election, before Trump was sworn in for his second term, Biden’s national security team needed to reach the president-elect about the hostages in Gaza.

According to Bill O’Reilly, they couldn’t get through.

So who did they call?

Bill O’Reilly.

Bill says he set up the conversation, moderated it, and didn’t offer a single opinion. About two weeks later, four hostages were released.

That story is a good example of his new book, Confronting America: What Has to Change.

Bill has spent more than 50 years around the people who make the news. Presidents. Political leaders. Media executives. Celebrities. He’s interviewed five presidents. He’s traveled around the world. And in this book, he names names. No anonymous sources.

It’s Trump. It’s Mamdani. It’s Soros. It’s Paul McCartney. It’s David Letterman.

In 1996, Bill launched The O’Reilly Factor. It was an opinion show that openly said it was an opinion show, and it became one of the biggest programs in cable news.

Now he runs his own media operations outside the traditional networks.

Fair warning: I was more opinionated in this interview than I usually am.

Bill has strong views on the media, Iran, New York City, the political parties, and where the country is headed. I pushed back in a few places, agreed with him in others, and the point is not that you have to agree with either of us.

Listen and decide for yourself.

At the end, I asked Bill about something he wrote in the book: his father’s final words were about never reaching his potential.

So I asked Bill whether he feels like he has reached his.

I expected him to say he was still chasing it.

He didn’t.

Episode Description:

Bill O’Reilly joins James to talk about Confronting America: What Has to Change, a book built from decades of firsthand encounters with presidents, political figures, media executives, and major events.

The conversation starts with O’Reilly’s account of helping establish communication between the outgoing Biden national-security team and President-elect Trump during negotiations over hostages in Gaza. From there, James asks what being close to power has taught him—and how much of what happens behind the scenes ever reaches the public.

They turn to the U.S.-Iran conflict, oil prices, the Strait of Hormuz, and the risks of making decisions when the consequences are difficult to predict. O’Reilly argues that the conflict became more complicated than initially expected, while James asks how media coverage shapes public perceptions of events like these.

That leads to a larger debate over political media. O’Reilly distinguishes the openly opinionated format of The O’Reilly Factor from what he sees as increasing ideological alignment inside news organizations. James pushes on whether opinion-driven cable news helped create that environment in the first place.

They also discuss the Trump administration’s fight with CNN, MS NOW, and Politico over White House access. Despite his criticism of those outlets, O’Reilly says he would have handled the dispute differently: keep them in the room, but don’t give them additional attention.

The conversation then moves to New York City politics, affordability, inequality, Mayor Zohran Mamdani’s agenda, municipal grocery stores, and the broader disagreement over how much government should intervene in markets. James is unusually explicit about his own views in this section, while O’Reilly explains how he sees the ideological divide reshaping both parties.

Near the end, James asks what changed when O’Reilly left corporate television and began running his own media operations. O’Reilly says independence giv