Can Trump run as an outsider?

But Trump’s unconventionality might, in itself, help him retain some kind of outsider cachet in a way that is unusual for an incumbent president.

“For any other president, yes, it is a challenge,” said Alex Conant, a Republican strategist who worked for Sen. Marco Rubio (R-Fla.) in the 2016 presidential primaries.

“But Trump is unlike any other president. Trump has been at war with the establishment since the moment he set foot in the White House,” he said…

“He is certainly an outsider to the political establishment. They still don’t get him and he is not coming around to their way of thinking,” said Barry Bennett, who worked as a senior adviser to Trump’s 2016 campaign. “He may live inside the gates but he does not live inside the establishment. … I don’t know anyone who believes he has become some kind of Georgetown socialite.”