During the days of slavery in America, there were plenty of people willing to risk their lives for freedom. Many did escape, many were caught, and many died, but there are a few stories of schemes that were so unbelievable that they not only worked, but went down in history. I particularly liked the story of Lewis Williams, who was arrested in Cincinnati for escaping from Kentucky. Williams was taken before a judge for an extradition hearing.
And they would have gotten away with it, too, if the leader of the black community in Cincinnati hadn't been a stone-cold badass by the name of Reverend William Troy. No sooner had he heard about the arrest than he was dreaming up a plan so insane that no one would see it coming.
As luck would have it, Troy knew another young man who bore a striking resemblance to Williams. And he also knew that some white people have famously questionable skills in the field of advanced telling black people apart. So when Troy heard that Williams had been seized, he made sure that a crowd of his fellow abolitionists rushed over and packed into the courtroom. Then they simply waited until everyone else was distracted by a dramatic legal argument, at which point Williams and his double quickly switched places and Williams crawled out the door on his hands and knees, hidden behind a wall of hilariously large old-timey women's skirts.
But that's not the end of the story, because he later had to escape from a safe house with another audacious scheme. Read his story and those of four others at Cracked. Link