It's not that events supposedly repeat themselves, but circumstances and choices do. And it's not supposed to be referring to an individual, but rather the overall course of human history. Like if you're a national ruler and you know that a certain choice will inevitably lead to war, and history has shown that in similar situations you won't win, and you make the choice you're dooming yourself to repeat it.
I don't buy into the cyclic theory.
I think if you drew the course of history it would be more like a swinging pendulum. Swinging from one extreme to the other and back.