His support of Trump also comes off the back of a long career dunking on the establishment, from his early material which covers subjects like voter discrimination, policy brutality, and the crack epidemic to his later work criticizing presidents who mistreat black people -- which includes Barack Obama (both for using him to appeal to the youth during his first election campaign and about how "nothing" changed in Chicago during his time in office) and George W. Bush for you know why, don't play this game.
West is a performer given to making huge proclamations and gestures, and he married into a family that turned "being rich and living in California" into an omnipresent dynasty our civilization hasn't seen since the Habsburgs. Also, during the 2016 election, Kim supported Hillary Clinton and Kanye donated $2,700 to her campaign, and that's off the back of another $15,000 he donated to the DNC in 2014 to assist with the midterms. If this doesn't turn out to be a piece of performance art, there's always the explanation that he's trying to jinx Trump 2020.
When he announced his newfound love of Trump, his first foray into punditry wasn't subtweeting Sean Hannity; it was posting poorly pirated versions of Scott Adams' videos -- you probably know Adams better as "the Dilbert guy" -- in which he rambles on for an insane amount of time about how Kanye West liking some crazy right-wing videos has caused reality to break. Furthermore, this whole incident reminds us about the last time a mainstream-rattling musical icon teamed up with a square, embattled president for his own self-serving, devious ends, none of which made anybody involved look particularly cool.