‘We’ll See,’ Trump Says on North Korea. And Iran. And Nafta. And So On.

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“The more people heard it, the less effective it became,” one of Mr. Obama’s speechwriters, David Litt, said in an interview, “which is one reason there were fewer ‘Let me be clears’ in the second term.”

Mr. Trump is different from other presidents because he seems to enjoy speaking extemporaneously on matters of consequence, said Ms. Jamieson, who has written extensively about Mr. Trump’s talent for using blunt language to subvert political norms. That approach has lent itself to a collection of presidential favorites: In Trumpese, she said, “many people are saying” means “I wish many people were saying this because I want you to believe they are.” “People don’t know,” she said, likely means “I just found out,” and “believe me,” on some level, may signal “I have real doubts.”

Mr. Trump’s modern predecessors, she said, tended to adhere to a tightly scripted approach. For example, she had a hard time imagining President John F. Kennedy saying “we’ll see what happens” while negotiating his way through the Cuban missile crisis.

“The presidents wanted to ensure that they knew what outcomes could be achieved and that their rhetoric could help them achieve the outcome,” she said. With Mr. Trump, “the signaling function is being eroded,” meaning that even words uttered by a commander-in-chief have a way of losing their power if they’re said often enough.

Speechwriters have often sought to hammer out such crutches, aware that an audience’s eyes and ears begin to glaze over if subjected to a rhetorical overdose. (Easier said than done, of course, when a president delights in veering off script.)

“If you keep forcing the same phrases into people’s ears all the time, people start to wonder what you’re actually meaning,” Matt Latimer, a literary agent and former speechwriter for Mr. Bush, said in an interview. He said the danger in Mr. Trump’s tendency could be, “after a while it’s like, ‘He really doesn’t know what’s going to happen, does he?’”

Mr. Latimer said that while Mr. Trump enjoys a strong economy and policy victories, like tax cuts, aimed at his base, it’s probably easier for him to wax extemporaneously. For instance, of the impending deadline on negotiations with Iran, Mr. Trump twisted the phrase to suit his penchant for showmanship: “Nobody knows what I’m going to do on the 12th, although, Mr. President, you have a pretty good idea — but we’ll see,” he said during a meeting last week with President Emmanuel Macron of France.

But Mr. Latimer, who scripted a president through the Iraq war and a looming recession, said Mr. Trump’s laissez-faire attitude probably would not last as consequential negotiations advance: “Free styling only works when things are going pretty well.”

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