Bill O’Reilly Says Warning to Trump Before Iran War ‘Haunts’ Him as Conflict Continues

Bill O’Reilly said Monday night that a private conversation he had with President Donald Trump before the Iran War continues to weigh heavily on him, revealing that he warned the president the conflict would be the “biggest gamble” of his life.

Appearing on NewsNation with host Leland Vittert, O’Reilly said he is troubled because the concerns he expressed to Trump before the war have unfolded in the way he feared.
“My own words haunt me,” O’Reilly told Vittert.

The former cable news host explained that he met privately with Trump in February and urged him to think carefully about the risks involved in confronting Iran.
“In February, I talked to the president, just him and me,” O’Reilly recalled. “I said this is the biggest gamble you have ever taken in your entire life messing around with these people. They’re irrational.”

O’Reilly went on to compare Iran’s leadership to militant forces from World War II, arguing they would not be willing to surrender despite military pressure.
“They are like the militants in Japan in World War II, in Germany in World War II, they’re not going to surrender,” he said. “It’s going to be exceedingly difficult, and you cannot count on the Persians to overthrow them.”

Looking back on that discussion, O’Reilly said the conflict has developed much as he anticipated.
“So my words haunt me, because it’s exactly how it came down,” he said.

The comments came after Vittert asked whether Trump was deliberately allowing the war to continue so it could conclude closer to the midterm elections, potentially giving Republicans a political boost.
O’Reilly dismissed that suggestion with a laugh.
“No, if he could get out of that thing now, tonight, he would,” he said, indicating he does not believe the president is seeking to prolong the conflict for political reasons.

The remarks echoed comments O’Reilly made last month when he reflected on his support for the Iraq War and admitted that decision continues to trouble him.
“I made a mistake with the Iraq situation, and that haunts me to this day,” O’Reilly said at the time.

He explained that his support for the war was based on reporting he believed to be accurate, including reports from The New York Times and other outlets claiming former Iraqi dictator Saddam Hussein possessed deadly weapons.

“Turned out to be wrong,” O’Reilly said. “Didn’t have any weapons of mass destruction, and the chaos that ensued brought a lot of pain on America. I was wrong. I was wrong. OK, there’s a reason I was wrong, but that still haunts me.”
In addition to reflecting on his past judgments, O’Reilly also expressed skepticism that the memorandum of understanding reached between the United States and Iran in June would ultimately bring the war to an end.

He said he believed the conflict was more likely to conclude through overwhelming U.S. military force than through the existing agreement.
O’Reilly’s appearance on NewsNation came one day after President Trump said a new agreement aimed at ending the war was “imminent,” signaling that negotiations remain underway even as questions persist about how the conflict will ultimately be resolved.