This post is separate from the video I made on this topic. This is solely designed to focus on who The White Shadow was in the context of The Boondocks show. My interpretation of the concept was simply a giving Chappelle's situation, as well as the case for many black people, a name.

Who is The White Shadow really? What was Aaron trying to do?
Aight, I'll bite. The White Shadow was simply supposed to represent this idea of independent reality. But, what's that? Well, I'm first gonna use a quote from Aaron from an AV Club interview.
"So, you know, it's all subjective. But I think the New Yorker article actually just taught me a really good lesson, which is–and now that I've been feeling stressed again, I'm reminded of it–it's all… None of this is actually reality. This is all interpretations of reality. You know, one writer's perspective, and you accept it for what it is, and you have to keep all of that stuff–everything regarding celebrity–at arm's length."
Now, Aaron was speaking about this in the context of an article painting a negative picture of him as lazy. Aaron loves The Matrix. He calls it a "parable of our time" on several occasions. And, The Boondocks episode, "The Real" was all about reality, the nature of it and how we perceive it.
Let's take a brief look at the scene between Huey and Jazmine that precedes the introduction of The White Shadow. Jazmine explains how the Tooth Fairy is coming, and Huey explains why it's a lie. Now, I'm assuming if you know this you know that the Tooth Fairy isn't real... right? But, to Jazmine, it is. That's her reality.
And while Huey ridicules Jazmine's belief in the tooth fairy, to Jazmine it's no more ridiculous than believing a secret government agent is watching him. Jazmine's role in this episode isn't just for cheap jokes, it's there to contextualize how silly Huey's perception of reality is to someone not seeing it from his eyes.

Now, does that mean it's not real?
It's real to him. An independent reality. Now, we gotta ask something different? Is something real because it's real to you or only when it's real to everyone else? Is reality dictated by yourself or everyone else?
If you're the only person that thinks something, society would dictate that you're crazy. And, to be honest, maybe you are. Or is that just what they want you to think?
Dave Chappelle once said:
“The worst thing to call somebody is crazy. It's dismissive. "I don't understand this person. So they're crazy." That's bullshit. These people are not crazy. They strong people. Maybe their environment is a little sick.”
Huey ends "The Real" with this quote:
"It's getting harder. Distinguishing reality from the illusions people make for us. And, the ones we make for ourselves. Maybe that's apart of the plan. To make me think I'm crazy... it's working."
Truth be told, reality is designed to give us comfort. Comfort isn't necessarily being happy with what we know, but simply in understanding them.
Jazmine finds comfort in her own reality. That's why she believes in the tooth fairy. Huey struggles to find comfort with his reality, because no-one else sees it. Jazmine has the lies of her parents to lean back on, whilst Huey has nothing, so he tries to reject it.

But you can't reject your own reality. Simply because it's how you see the world.
It's easy to become paranoid when nobody sees what you see. It's easy to be called crazy when the world doesn't think like you. It's like The Matrix. Everyone is plugged into the same system. And, when your thoughts don't fit with the system, you're deemed as crazy. The people that control the world will tell you that, the people brainwashed by the system will tell you that, and eventually, you'll start to believe it. Just like Huey said: "It's working."
Season One had this obsession with dreams, miracles and religion. The White Shadow could be any of the prior. He could be God. He could be The White Man. He could be a dream. The Govenement or whatever. But, that's not for us to decide. The only thing we truly know is that it's Huey's reality, and like Aaron said earlier, we have to accept that.
Ultimately, The White Shadow is an exploration into independent reality, and how we dictate what is real and what is fake. The episode is called The Real because it explores the lies we tell ourselves and the lies we tell others. There is no singular reality.
Just our own independent truth.