Like, what kind of dictator are we talking here? Is this a Lord Vetinari benevolent dictator, or your typical generic slimeball autocrat?
Personally, I’d like to think that if they did become the latter, they’d be so far different from the person I love that I would break from them. Thoughtfulness, intelligence, and consideration aren’t usually things I see associated with dictators, you know? But people have an incredible capacity to isolate and put on different masks between their personal and professional lives…
This is fundamentally a variation on the question of a Temporal Paradox, also known as a Grandfather Paradox (“You go back in time and kill your grandfather. What happens?”). Although no killing happens in this variation, the basic idea is the same: Information is transmitted to the past from the future, but results in a situation where it cannot be transmitted in the first place.
Accordingly, there are several hypotheses to cover this. This isn’t even all of them: