How about "Yojimbo (from FFX) at the Gold Saucer"?
He walks over to a roulette table and puts down a pile of gil. You must dps that pile to reduce the amount he's bet. But you reasonably cannot zero it.
Then everyone is transported to random spots on the roulette wheel, and 3 balls drop on you, doing 5k if they hit you. Then the wheel spins and you have to dodge the randomly bouncing balls.
If Yojimbo wins, his distributed winnings appear and you have to knock his tokens (moved by hitting them) from high win zones to low win ones.
After 10 seconds, Yojimbo collects.
If he does not win, then he claims the game is rigged, starts throwing aoes at the table/arena, gaining 5% more gil for every person hit. Then collects 75% of his original bet.
So now Yojimbo has some cash so it is back to a normal arena. Here Yojimbo will throw a pair of dice into the air and smack them with his sword in a random direction. Getting hit by a die deals 10k damage, knocks you to the wall, and stuns you for 10 sec.
Depending on his die roll (2-12), he will perform a sequence of attacks.
Every time he does this, he loses X gil from what he won at the roulette table until he runs out and plays roulette again. But once he's "broke", he takes 10x damage for some 20-30 seconds.
So its a 2 part fight.
First you have to dps, avoid, and coordinate to minimize his earnings.
Then you have to deal with a flurry of random attack sequences, including landslides, divebombs, doom, petrification.... just ALL the good stuff.
And IF you win... IF...
You get ALL the "special gil" he used during the fight, and access to a "store" where you can buy any raid gear, including an exclusive weapon.


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