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.