Political allies and former advisers concede that Trump has trouble holding his tongue — especially when he can boost his image or clinch an argument. The president’s flair for speaking freely, they say, was formed during his heyday as a New York tabloid fixture, when he straddled the worlds of entertainment and business and learned the power of gossip and illicit truths.

“He’s good at keeping secrets that involve him,” said Sam Nunberg, one of Trump’s earliest 2016 presidential campaign aides. Invoking the Yiddish word for a female gossip, he added of Trump: “On the other hand, the guy’s a fucking yenta.”…

“Could President Obama keep a secret? Ask Osama bin Laden,” said a former senior Obama aide, noting that Obama spoke at the 2011 White House Correspondents’ Dinner on the eve of the raid that killed the Sept. 11 mastermind. “Didn’t show his hand at all. “