I am guessing that probability is close to zero. The presidential race is a multi-stage contest. Trump happens to be good at working the current stage, but his current actions will eventually catch up to him later. I used to be a big fan of the show Survivor. Russell Hantz had a similar run: twice in a row he made it all the way to the end, but because of how he got there he could not actually win the grand prize. Trump is similar: he is going to pull a lot of stunts, get lots of attention and spend lots of money. Then the rubber meets the road and he'll lose. The real question is whether he is going to be the Republican nominee, because if he is then they'll be handing the victory over to the Democrats. My guess is that like many vanity candidates before Trump, he'll fizzle out before the primaries, but if he does make it even more hilarity will ensue.