In Medium, Matt Haughey puts his finger on the peculiar intimacy Trump conjures with his listeners — a skill he shares with that other performer-turned-pol, Ronald Reagan:
When you see Trump speaking at his stops, he’s clearly talking off the top of his head, and that can be refreshing when compared other political candidates that go off prepared remarks. Politics tackles big important problems that require research, so remarks are usually prepared well in advance. I came away from watching Trump realizing he’s the next phase of George W. Bush, who famously spoke in simple terms that when analyzed for grammar showed up as 8th grade level (most political speeches are at 11th-12th grade level). Everyone watching can understand every word and every sentence, even though what he says usually doesn’t have any specific steps or concrete information on how he’d combat problems.
In these venues Trump is clearly a guy talking off the top of his head, telling you what he really thinks, and it really did feel like he was “not like all the other guys” as he would describe it. People like that for the same reason they liked George W. Bush who I often heard described as “a guy you’d like to have a beer with.”
Trump talking at one of his events is like listening to a podcast, and people might like him for all the same reasons they’d like podcasts. There’s a combo of informality and intimacy that makes you feel like this one person is talking to just you, and telling you amazing things.