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It's pretty easy.
The poorest billionaire would be the one that is closest to having just over one billion dollars.
The worst spartan would be the one that is least effective as a difference-making special forces soldier.
My vote is Emile - I love the guy, but a shotgun is not a sniper rifle and I don't think he got one kill in my whole campaign on Heroic. As far as non-game canon goes, any member of Alpha company from the first Spartan III class that broke team cohesion and got the others killed without achieving much of anything.
Actually, Emile's from Alpha company. Not a co-incidence.
[Edited on 05.15.2011 8:40 PM PDT]