1988. Trump is way less charismatic than W Bush and his gaffes have no positive spin. If you need any evidence that he's not play 4-dimensional chess, just look at his comments about Judge Curiel. There was no benefit to his poll numbers, in fact they went down. He got a lot of media attention out of that event, and it didn't benefit him. He's not a tactical genius; he's an idiot.
As Obama said, we all make misstakes.
Trump is not an idiot. Actually, I don't think, that there is anybody, who'd be that close to winning an election, after spending so little money to ads.
I'm not a subscriber to the "great man" theory. Trump tapped into the discontent brewing since 2009. His personal acumen has little to do with it beyond fueling the flames of populist resentment. The problem is, his controversial remarks have not been helpful since he won the nomination back in May.