Trump is a boomer. Mattis, Flynn, Tillerson, too.
There was a boomer split in the late 60's; hippies/non hippies.
Trump, and other non hippies are settling the score for what the hippies did then and have been doing since.
Remember back then the population exploded (baby boom) but the slots available for what kids aspired to didn't. Still 11 starters on a football team, still 5 starters on the basketball team, etc.
There were suddenly a lot more kids who didn't make the cut.
Look at the Clinton's for the Hippie response; brain better than brawn, fuck the rules, fuck any traditional method to a position of authority and fuck anyone who poses a challenge by wielding any power they deem necessary.
Have to take a good look at the players, how successful they were then, and try not conflate boomers with hippies.