Where should the U.S. intelligence community's first PowerPoint presentation for Trump begin?
"It beggars the imagination," said former CIA director Michael V. Hayden, who was among those who briefed President Obama after the 2008 election. "Given that [Trump's] public persona seems to reflect a lack of understanding or care about global issues, how do you arrange these presentations to learn what are the true depths of his understanding?"
Director of National Intelligence James R. Clapper Jr. said last week that U.S. spy agencies have already begun planning briefings for Trump and his presumed Democratic opponent, Hillary Clinton, although neither is expected to receive an initial briefing before party conventions conclude in July.
In response to a question from the Daily Beast, Clapper alluded to concern for the handling of any secrets shared. The process is designed "to ensure that everybody gets the same information and that we do comply with the needs to protect sources and methods."
Clinton's ability to protect sensitive information has also come under sharp criticism, after the disclosure that she relied on a private e-mail server to communicate with subordinates while serving as secretary of state. But she has likely participated in thousands of classified briefings — unlike Trump who has never been privy to the government's most closely guarded secrets.
"This is a person who doesn't seem to have much of a filter," said Aki Peritz, a former CIA analyst who contributed to the President's Daily Brief (PDB) — the digest delivered each morning to the Oval Office. "The scary part is that nobody knows who he really is. Is he this blowhard demagogue we see on TV or is he really a sophisticated consumer of information that will keep this information close to his chest?"
Either way, Director of National Intelligence and CIA analysts may have little leeway in what they present. The decision on how much to share and when are traditionally made by the sitting president.
"The candidates get the same information — no favoritism," said David Priess, a former CIA briefer and author of "The President's Book of Secrets," a history of the PDB. "It's not that the briefer can freelance."
Pre-election briefings tend to be overviews of spy agency assessments of major topics such as the civil war in Syria. That changes after Election Day, however, when separate teams are sent in advance to the candidates' headquarters. The winner is given a deeper briefing on more highly classified material, including CIA operations overseas. The other team heads back to headquarters without briefing the losing candidate.
Analysts selected for such assignments tend to be among the most polished and experienced in the intelligence community. "They are going to be very professional," Peritz said, but Trump poses unique complications. "He has all kinds of relationships with Chinese investors and Russian investors. He's spoken very highly of our adversaries. And he's talked about using torture and waterboarding and attacking people's families. All these things are going through the analysts' minds."