How the Trump Campaign Is Drawing Obama Out of Retirement

During the transition, in what looks in hindsight like a preview of the presidency, one Trump aide got the idea of printing out the detailed checklist of Mr. Obama’s campaign promises from the official White House website to repurpose as a kind of hit list, according to two people familiar with the effort.

“This is personal for Trump; it is all about President Obama and demolishing his legacy. It’s his obsession,” said Omarosa Manigault Newman, an “Apprentice” veteran and, until her abrupt departure, one of the few black officials in Mr. Trump’s West Wing. “President Obama will not be able to rest as long as Trump is breathing.”

When the two men met for a stilted postelection sit-down in November 2016, the president-elect was polite, so Mr. Obama took the opportunity to advise him against going scorched-earth on Obamacare. “Look, you can take my name off of it; I don’t care,” he said, according to aides.

Mr. Trump nodded noncommittally.

As the transition dragged on, Mr. Obama became increasingly uneasy at what he saw as the breezy indifference of the new president and his inexperienced team. Many of them ignored the briefing binders his staff had painstakingly produced at his direction, former Obama aides recalled, and instead of focusing on policy or the workings of the West Wing, they inquired about the quality of tacos in the basement mess or where to find a good apartment.

As for Mr. Trump, he had “no idea what he’s doing,” Mr. Obama told an aide after their Oval Office encounter.

Jared Kushner, Mr. Trump’s son-in-law and close adviser, made an equally indelible impression. During a tour of the building he abruptly inquired, “So how many of these people are sticking around?”

The answer was none, his escort replied. (West Wing officials serve at the president’s pleasure, as Mr. Trump would amply illustrate in the coming months.)