Why does Trump care so much about Time — a magazine that, like all national magazines, has been hit hard by the fracturing of the media and the changing advertising landscape?

Because all of Trump’s ideas about the media were formed in the 1980s. And at that time, Time was a massively important part of the culture. It was a tastemaker — and breaker. And, most importantly for Trump, it had a cover. A cover that, if you were on it, signified success in the broader culture.

That sort of recognized success is what Trump has spent his whole life craving — and disdaining when he doesn’t receive it. He views himself as someone who, despite his successes and wealth, has never been accepted into the clubs and communities that he covets. He is forever the guy with his face pressed against the glass, watching the people he wants to be friends with eat, drink and be merry in clubs they won’t let him into.