One of three scenarios...
1) A wildly popular incumbent president (70-80% approval rating) presiding over a booming economy and a peaceful world stage plunders a terrible opponent.
2) A wildly unpopular incumbent president (15-25% approval rating) presiding over an economic depression and/or an unpopular war gets plundered by a flawless challenger.
3) A colossal third-party candidacy takes root and splits one of the parties in half, resulting in the other party benefiting from the fracture.
I feel 1 and 2 are far more likely than 3. Even if the 3rd scenario happens this third-party likely wins enough electoral votes in junction with one of the major parties to prevent the other major party from clearing 500. Like it could be a 450/50/38 split.
Due to current polarization I think even 400+ would be a stretch. Obama only got 365, and that was after 8 years of a Republican President who had 25% approvals at the end, a Recession occurring, and two unpopular wars. Even though he was viewed as a messiah by some he couldn't clear 400.
I can't even imagine how bad, or good, things would be for someone to clear 500. Politics have drastically changed since Reagan in 1984.