‘This guy was a wanted terrorist’: ‘Fox & Friends’ host shows some spine as Donald Trump displays he’s a poor judge of character

On May 14, 2025, Robert Greenway, a former National Security Council official under President Donald Trump, appeared on Fox & Friends to defend his former boss’s latest diplomatic head-scratcher – a cozy sit-down with Syria’s newly minted president, Ahmed al-Sharaa.

The meeting marked the first time a U.S. president has met with a Syrian leader in 25 years, a diplomatic icebreaker that left many wondering if Trump simply lost his Rolodex of more reputable global leaders.

Fox & Friends co-host Brian Kilmeade, not usually known for his hard-hitting pushback against Trump, actually managed to raise a skeptical eyebrow this time. He cut to the chase, reminding viewers of al-Sharaa’s not-so-glamorous past.

“This guy was a wanted terrorist”

In the segment, Kilmeade said, “It’s interesting too, because this guy was a wanted terrorist who would have gotten you $20 million if you captured him. Now he’s got a suit on and a trimmed beard, and we’re greeting him, but he says he’s reformed his ways.”

For those unfamiliar, Ahmed al-Sharaa (once known as Abu Mohammad al-Julani) rose from the murky depths of the global jihadist movement to his current position as Syria’s head of state. In his earlier days, he was more likely to be spotted clutching an AK-47 than adjusting a silk tie.

Born in Riyadh in 1982, al-Sharaa cut his teeth in the violent underworld of al-Qaeda in Iraq, where he spent time as a U.S. detainee before re-emerging as the head of the al-Nusra Front, al-Qaeda’s Syrian affiliate. This same al-Nusra Front, by the way, earned its terrorist stripes by fighting both Syrian government forces and rival jihadists alike – a real overachiever in the chaos department.

In a twist befitting a late-season plot arc, al-Sharaa declared his “independence” from al-Qaeda in 2016, rebranding his group as Hay’at Tahrir al-Sham (HTS).

Trump’s “big, beautiful” plan to rewrite Middle East playbook

So, why did Trump, a man with a self-proclaimed gift for sizing people up, sit down with this questionable character? It’s all part of his ‘big, beautiful’ plan to rewrite the Middle East playbook.

The meeting, reportedly brokered by Saudi Crown Prince Mohammed bin Salman and Turkish President Recep Tayyip Erdoğan, is part of a broader push to reintegrate Syria into the global fold. Trump, always one for grand gestures, even floated the idea of Syria joining the Abraham Accords, normalizing relations with Israel – a move that would certainly turn heads, if not stomachs.

Of course, not everyone is on board. Greenway, doing his best to put a polished spin on the whole affair, argued that engaging with al-Sharaa is a necessary evil if the U.S. hopes to curb Iranian influence in Syria and stabilize the region.

In other words, Washington’s foreign policy has once again veered into the morally murky waters of ‘better the devil you know.’ Time will tell if this latest Middle East gamble ends in a diplomatic coup or another foreign policy hangover.