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.
A friend took me and our wives to dinner one night. Middle of the meal he wants to talk politics and I don't.
I've had a policy since I was a kid of never talking politics with someone I'd like to stay friends with. Reason being that any political discussion only goes two ways: I give a simple answer that is unexpected and get barraged with a bullet list of talking points we could address, but the listener is too distracted by there being more talking points in the queue to hear any of my responses. The other way is I give a simple answer, the other person chuckles and we never talk about politics again (because we agree, or because he's so alarmed and wary he doesn't want to talk to me anymore).
His question was, "Can we talk about Trump?" And I responded, "Can we not and tell others we did?" He laughed at the joke and pushed forward, "I want to read a post I saw and get your response to it. It makes sense to me, but I wanted to know what your take was." I wince, this is the talking-point barrage happening pre-conversation, and say, "That sounds like a terrible idea over dinner, and our wives are here." His wife pipes up, "No, I'm interested too." Mine stays quiet.
Sufficiently emboldened, he pulls out his phone and begins reading. This is the primary cycle of the 2016 race, and honestly I'm doing my level best so far in not paying close attention to anything. I've not voted for a primary candidate that went on to get the nomination at any point before. Every winning nominee since I'd begun voting wasn't my pick (or even second pick). In 2016 I had less than zero interest in following the primary candidates closely.
What he read was a rant to the effect of "Every candidate is better than Trump in every way." To which I asked, "Does that include Hillary?" He cocked his head and finally asked carefully, "Are you saying Hillary is not better than Trump?" I shrugged and said "Trump is not at the bottom of the list, nowhere near it. Hillary, however, name a single candidate in this field you think is worse than her. I can't."
He finally said that he wasn't thinking of her as a serious candidate, more of a perfunctory inclusion. But he admitted, no, nobody is worse, even Trump. So I finished with "There's a number of people I'd be happy to see make it through. Trump doesn't bother me, and I don't know why he bothers other people so much. Hillary, however, bothers me enormously. I think we have many more important problems to consider before we get to how good or bad Trump is."
Later, Hillary won the nomination, and at that point I was totally invested in Trump.