I've actually, as a DM, rolled trip 20s three separate times, twice against player characters, once for an NPC attacking a Slaad. Both times it resulted in player death, and much endless bitching. Sorry guys, player death happens. No character is invincible, and sometimes as a DM it's important to remind the players that they are mortal.
But last night, my wife's Paladin 5/Pious Templar 4/Griffon Rider 2 rolled trip 20s on a smite against a mature adult dragon (CR 13), slaying it instantly. Now she's a Griffon Rider 3.
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