Washington, Jefferson, Adams, Franklin and Crockett.
Woken from cryo-sleep to join the civilization building party traveling to a newly discovered earth-like planet in a nearby star system. They would all help write the Code of governance for the new home world. Washington would oversee the military, Jefferson would work with architecture, civil engineering and public works, Adams would be responsible for the legal code and courts of law, Franklin would deal with agriculture and natural resource allocation and utilization, and Crockett would take care of internal security, law enforcement. Once the groundwork was laid, there would be open elections for all citizens to vote to either keep or replace the original office holders. No individual would have complete authority over their tasks, they would be more like project managers to ensure the quality and efficacy of the systems implemented.
Churchill could come too. He would be in charge of all public address and ambassadorial duties to outlying worlds.
Hillary Clinton could join as well for female representation, though she is closer to a gentleman than a lady. Her job would be to stand in the agricultural sector as a scarecrow in order to frighten the native fauna away from the crops. However, she could only work the night shift, lest her terrible visage stunt the growth of the plants she guards.
"I don't believe in guilt, I only believe in living on impulses"
"Stereotypes about personality and gender turn out to be fairly accurate: ... On the binary Myers-Briggs measure, the thinking-feeling breakdown is about 30/70 for women versus 60/40 for men." ~ Bryan Caplan
Basically, you're asking for morally ambiguous but stylish rogues who get shit done?
Andrew Jackson: He may be a bastard, but he's also a bad-ass. Battlefield expert.
Theodore Roosevelt: Do I really need to explain? Roaming operative.
Otto Von Bismark: Just about the craftiest son of a bitch who ever lived. Master strategist.
Winston Churchill: Duh. The driven, charismatic leader who is everyone's second choice as leader, and therefore the only one they would all accept.
Catherine the Great: always comes out ahead, and romantic tension for 'extrordinary gentlemen' who know its a bad idea, but just can't stay away from her.
Alcibiades would probably be the best choice for traitor, working with the villian Rasputin (for the sake of entertainment, we'll pretend the latter is actually a hard-to-kill sorceror rather than an illiterate con-artist). They both manipulate Alexander the Great into working for them, untill his services are no longer needed.