Either like Wallace today or like Bryan in the 1940s. If he loses the nomination and leaves politics for good, he's clearly Wallace. If he wins the nomination and then loses the general or keeps running again and again into the 2020's, parts of his platform will eventually become mainstream. If so, will a toned down version of Trump eventually win in a landslide?
This. The most likely scenario in which this would occur is a Wall Street crash that occurred during a neoliberal Democratic administration (an HRC or say a Cory Booker) - this wouldn't convince people that a return to Reagonomics would be the answer and I could see folks going to someone like Trump in that situation.