The playing field is a Holodeck, the tech level and environment is equivalent to Rome before its fall. They all start out separately in the City of Rome yet at the same time, with nothing but a small amount of local currency and robes. Using all of their leadership, mental and physical capabilities, who would win and how?
I vote Captain Picard.
With his tenure, knowledge base, and obvious abilities to lead a crowd, I see him gathering followers and leading them to victory. It also helps that he had special mind abilities in another universe altogether and his special X-men team
And didn't Q at one point or another make him a Q or something? I thought there was an episode. So yes.. Picard is the obvious, and solid choice!
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RE: Captain Series Brawl!
Riker was made Q, but refused to be Q
I think it would be a toss up between Kirk and Picard, there charisma is so high they can gather followers. They have very different approches to it. They both ended up rewriting a lot of Star fleet laws and rules. They other captians may have had great stories and remarkable out comes.