There is a chance of success based upon relevant stats and traits and one of the outcomes is that failed assassination attempts often result in them becoming harder to assassinate as they take more precautions and occasionally show mental side effects.
Now look at Fidel Castro and the clownish job of the CIA's loony toons assassination attempts.
It sounds absurdly gamey at first but assassination resistance may be effectively trainable like immune systems or antibiotic resistance. There is nothing magical about it - the target simply builds up infastructure of countermeasures, deliberately not following schedules, and less physically accessible to anyone unvetted. If in the dirty business of sending assassins in the first place quantity does not have a quality in its own but makes defenses stronger - strategically what is needed is one to do it right.
"Stop sending people to kill me! We’ve already captured five of them, one with a bomb and another with a rifle… If you don’t stop sending killers, I’ll send one to Moscow, and I won’t have to send another"