MSNBC’s Lawrence O’Donnell said President Donald Trump “is clearly off his game” after watching footage of his Oval Office meeting with Canadian Prime Minister Mark Carney on Tuesday.

“The Canadian prime minister both humbled and humiliated Donald Trump at the same time without Donald Trump having the slightest idea it was happening,” he said on Tuesday night.

O’Donnell said there’s been a “steady stream of that sort of humiliation,” starting with French President Emmanuel Macron’s visit in February and when British Prime Minister Keir Starmer stopped by days later.

Later in the segment, O’Donnell slammed Trump’s “utterly demented attempt” to turn Canada into a state. Carney, he noted, responded by saying “absolutely no to Donald Trump to his face.”

But Trump, he said, barely noticed.

“Donald Trump had no fight in him today when the very polite Canadian beside him talked rings around Donald Trump like a ring master in a circus with a trained animal, threw in some magic words that sounded flattering enough to Donald Trump so that Donald Trump actually ― and you’ll see this ― ends up nodding and agreeing with the man who is humiliating him and defeating him right there in the room on TV, ” O’Donnell said. “No president has ever lost more in one conversation in the Oval Office than Donald Trump lost in these 90 seconds.”

O’Donnell rolled the footage of the meeting, where Carney told him Canada would never be for sale and would not be a U.S. state.

See more from O’Donnell’s Tuesday night monologue: