I can see it now. I predict that he wins the 2024 election for sure. Another president did this years ago. Some one please chime in with his name.
Everybody has an opinion, but the name is Grover Cleveland.
Personally, I think that the chance of this happening is low, but non-zero, of course.
Chance = Yes.
But the only possible chance is Donald J Trump winning, the former President, not any of his sons or anything along those lines.
If anyone would like to make a new "Trump or not Trump" 1:1 bet for 2024 - you know where to find me 
. Same conditions as per OP, just add 4 years to dates. 0.01 BTC minimum, 1 BTC max (total budget). Escrow required unless you're in my trust list and the amount is 0.1 BTC or less. To make it more bearable let's make it any Trump and throw in Jared too.
You bet on: Donald J Trump, or one of his children (Ivanka, Don Jr, Eric, Tiffany), or one of his past/current spouses, or Jared Kushner.
I bet on: none of the above.
Any takers?
Let's see how sure
. Same conditions as per OP, just add 4 years to dates. 0.01 BTC minimum, 1 BTC max (total budget). Escrow required unless you're in my trust list and the amount is 0.1 BTC or less. To make it more bearable let's make it any Trump and throw in Jared too.You bet on: Donald J Trump, or one of his children (Ivanka, Don Jr, Eric, Tiffany), or one of his past/current spouses, or Jared Kushner.
I bet on: none of the above.
Any takers?
I predict that he wins the 2024 election for sure.
Let's see how sure
I'd like to hop in on your side of this bet, SuchMoon, if we get enough people for that
Only person with a real chance, like I said above, is Donald J Trump. None of his sons or Kushner is going to be able to get people to vote for them like the elder Trump did.