I wouldn't trust you in a bet no matter what.
In any case, the way you presented the bet is fucked up.
Do you mean that in 3 years and 3 months from now you will bet me $100 that Trump was never a dictator during that time? Or are you making some kind of bet NOW...that will be settled in 3 years and 3 months?
Either way, there are two things wrong with that.
One...I am 89...and there is a good chance I will not be here for the bet.
Two, the decent, intelligent folk of America may be able to stop you ignorant, disgusting people from installing him as dictator.
Either of those give you a distinct advantage. So you would have to give me odds to compensate for that advantage...something you did not discuss.
But even if you did, as I said above, I wouldn't trust you in a bet no matter what.