Mathematically Assassinate is Bad

Commenting in an old thread, but for anyone Googling I just wanted to say this is terrible analysis. Less important but the guy didn't need to run a simulation. You can just calculate the exact odds with basic stats.

Anyway, Rogues have tons of things that can boost their stealth to make the surprise round nearly guaranteed. You also don't need to win the initiative to activate the ability. If you lose initiative the creature is surprised during their turn and loses their turn. Then next turn they go first. And you're going to get advantage on the attack. The odds of landing a hit are closer to 80-90% with the right combination of abilities.

There are also ways at higher levels and with multiclassing to get off multiple attacks and add bonuses with hunter's mark, sharpshooter, sneak attack, etc.

If you land multiple attacks with additional damage from abilities and have guaranteed crits on all of them you're going to do heaps of damage.

/r/dndnext Thread