We have to be honest: "The People Could Fly" isn't all that focused on its characters. It is a folk tale, after all.
Like most folk tales, "The People Could Fly" treats its characters as symbols rather than individuals. This has to do with the way they're created: Instead of having only one author, like a novel, folk tales have tons of authors. This is because they're the result of a bunch of people sharing a single story, each shaping it in their own way before passing it along to the next storyteller who, in turn, adds their own take on the tale.
All of this is to say that you have to take old man Toby at face value. Toby represents a strong leader, selfless and completely dedicated to the good of his people. You don't have to do much digging to understand him, but that doesn't have to be a bad thing.
Let's go ahead and list the guy's accomplishments, shall we?
As you can see, Toby is a Moses-like figure, leading his people from slavery into freedom. Interestingly, however, he follows the people, flying "behind them [and] takin care of them" (27). That's true leadership. It would've been easy for Toby to lead the pack (more like flock) and take all of the glory, but he prefers to humbly bring up the rear. You know how the captain's supposed to go down with the ship? Toby models this maxim through and through.
Interestingly, Toby never gets emotional throughout the story. He isn't " laughin" or "cryin" (28) as he flies away from his former prison. Instead, "his gaze fell to the plantation where the slaves who could not fly waited" (28). Toby is an objective observer of the situation—after all, he seems to be the only one who actually remembers the past well enough to know they can fly. So what exactly makes Toby different than everyone else?
The story only hints at an answer. Toby is referred to as the "seer" (28) as he looks down on the people who remain enslaved, echoing the idea that he is a sort of observer. But this is a play on words—a seer is also someone who can look into the future. Similarly, this term brings to mind the Overseer, the cruel rider who leads the Driver to his victims. Toby plays a similar role for his people—the only difference being that Toby uses his vision to realize freedom instead of oppression.
But there's another meaning tucked in there, too: Toby is the only person who can see past the surface into the power that's on the inside. He's the only who can tell which people have the power of flight and which don't. No matter how much they're treated like they're less-than-human, the people can always have faith that Toby is looking past the exterior and into their hearts.
So we can only hope that Toby goes on to live a long healthy life, chilling in the clouds with Hawkman and Superman, maybe even taking a trip to the moon if he can fly that far. That's a story we'd love to read.