When he announced his running prior to 2016, I thought it was a joke.
The apprentice guy? I was born in 92 and really just hardly aware of him except for the apprentice, of which I only watched a few of the celebrity apprentice episodes because it had celebrities on that I liked such as Gilbert Gottfried and Penn Jillette.
So I didn't really care for Trump for two reasons.
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I associated him with reality TV and I did and still do despise reality TV. I saw it and still see it as one of those things that decayed the American culture.
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When he was the subject of a comedy central roast around the time he announced he was running, he didn't seem like he could take a joke.
I've since seen that Trump's not the type of guy who does big hearty showy laughs. If he's amused by something he'll just sort of smile. But at the time, I didn't think he had a sense of humor about himself, and I've always been someone who's wary of people who can't take jokes about themselves.
But what changed for me officially was when I saw a video of his, one of his campaign videos addressing the problem of political correctness in the culture and stifling free speech.
That alone was enough to ensure I was behind him 100%. I never saw any other "conservative" politician boldly address this issue or even address it at all really.
Mostly it was just us on the internet fighting the culture war who bothered to address and fight political correctness. Where was John McCain's take down of PC culture? Where was Mitt Romney's takedown of PC culture? But here, the guy who I thought was just doing this for attention as a reality TV guy, is the only one to flat-out say, political correctness is a problem and needs to be addressed.
So that video made me a Trump supporter. Then seeing how the mainstream media treated the man made me see things even clearer.
The moment John Oliver mocked him I know I was locked into licking him.
I knew he was something of a media mogul, had cameos here and there in TV and movies but really didn't think much about him.
But then Hillary showed up and John Oliver thought Trump was a joke worth mocking over the plutocratic puppet which exemplified the authoritarian Left.
Easy side to pick and what an enjoyable ride it's been too :)
I was, and am, a classic liberal (In the non-US sense) and so would have been considered a Lefty all the way through Obama's administration. I know lots of people who also jumped ship as soon as Hillary showed up and so they did that one to themselves.