I'm A Banana
Potassium-Rich
Whereas my character doesn't see himself like that at all. He sees himself as more like Odysseus -- a guy who succeeds through cunning, trickery, and pragmatism, who outsmarts dragons and tricks fiends, who couldn't care less about Little Timmy the Village Cripple (unless he's got some valuable information to share), who's just as likely to keep the macguffin for himself as he is to return it to its "rightful" former-owner, and who intends never to find out wheter or not he can take a bullet wound in the face and survive. And because of that he'll still be alive at the end of the day, listening as all the other dead heroes are memorialized by the bards.
Odysseus wooed and slept with saucy foreign women and never once worried about catching the ancient greek herpes.
Odysseus spat in the face of GODS, in fact, one of the most ancient and powerful of all gods, and lived to tell the tale.
When faced between Scylla and Charibdis, Odysseus didn't say "I will stay here because it is safe." He said "I need to get home, and they are in my way, so I will go THROUGH them. Damn the danger!"
Odysseus was VERY heroic. He recklessly confronted dangers of an extreme and obviously deadly nature and lived to tell the tale. He lived because of his cleverness (and no small amount of divine intervention), but that doesn't eradicate the fact that he most definately did not play it safe. Safe would have been accepting his fate. Safe would have been not going to Troy. Safe never entered into his equasion.
Apparently, the really smart BBEG isn't all that smart, because it's a foregone conclusion that the heroes will eventually win and the BBEG will always lose at a dramatic and climactic moment because that's how games of HEROIC fantasy gaming work (everybody knows that, duh!). So no matter how well he plans, how much money he spends or how cunning he thinks he's being, he ought to know he is done for because he's not just up against any old opponent, he's up against a band of HEROES.
When he notices that someone just built a new railroad line leading directly to his hideout, the really smart BBEG realizes it's time to take his treasure and retire to a small village, before the HERO EXPRESS chugs it's way over him.
Evil doesn't always loose. You're wrong to assume so. You are once again mischaracterising those opposing you of wanting it easy and simple, and that remains as untrue as it ever was. People don't want it easy. They just want it fair and fun.
No, evil attains many victories. But unless those victories make for a more interesting game, they really don't matter, and probably shouldn't be included. And certainly D&D should be played with the assumption that it is fair and fun.
This magical death lever is crazy out-of-the-blue assassination that only the very paranoid characters (and, thus, not fully apt for the vast majority of D&D characters) or most prescient metagame thinkers would avoid.
This makes it unfair, and, for most, not fun.
"Unfair" is a completely valid and apt label for this scenario, and one doesn't need to resort to ad absurdium attacks to disagree, merely just be comfortable with paranoid characters or presceint players.