Sounds... awesome... if you enjoy pvp? Did you have any thoughts for a more accessible pve component to this or would this be an event where everyone that isn't a hardcore pvp player just sits it out and continues doing whatever they would have been doing anyway?
Something somewhere in between this idea and the bounty event could be interesting though. Sign up for it and it puts you in a queue, get on a team (bolstered but not role neutral) and enter the arena to face off against a team made up of one random enemy of comparable strength to a kingpin and three random enemies of comparable strength to the henchmen.
Or maybe there's room for both. You select which one you'll queue for in the conversation when you register for a match but the warzone and flashpoint will count towards the same event daily. Maybe even make the daily require 2 or 3 victories so there's room for players to decide whether they want to do it all one way, all the other way, or with a mix of both types of matches.
Do you remember the KOTOR Dueling Ring of Taris?
Something else to point out to me that I apparently forgot 99% of what happened in those games after I completed them.