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THE RULES
* Obi-Wan only has to survive 30 seconds against his opponents. If he does, he goes to the next round.
* In character.
* Full heal after each round.
* Fight on Utapau, no droids/people, starting distance 10 meters.

THE GAUNTLET
1. General Grievous / Durge / Boba Fett
2. HK-47 /Pre Vizsla / Jango Fett / Bossk / IG-88
3. Agen Kolar / Kit Fisto / Saesee Tiin
4. Jaina Solo / Plo Koon / Tresina Lobi / Antares Draco
5. Savage Opress / Asajj Ventress / Darth Nihl / Darth Talon
6. Count Dooku / Darth Maul / RotJ Luke Skywalker
7. Mace Windu / Anakin Skywalker / Darth Krayt
8. Ajunta Pall / Karness Muur / Exar Kun / Darth Tenebrous / Darth Venamis

Dies at 1, which should honestly be above 3

He won't survive 30 seconds?

Not to mention Boba and Durge utilizing their equipment would threaten Grievous, who would take a huge space around Kenobi by his size, essentially hindering them. Boba and Durge won't be able to use heavy artillery with huge ally fighting Obi-Wan in close combat.

Dies horrendously at 2.

I don't see him surviving any of them tbh

They could still spam flamethrowers while Kenobi's dueling GG, or GG could step back while they spam Obi with explosives and the rest of their arsenal then GG charges in to clean house.

Done at one unless surviving counts as being crippled for life.

He has to survive 30 seconds only, if he's alive that's enough

There is a chance that Kenobi might have a pulse at the end of the 30 seconds for round 1; I'll push him to two but that's it.

Sonic Screamers would also be pretty bad for him, of which Boba and 88 have.