Jay tells Robinson that Barack Obama’s 2008 election “actually renewed my spirit for America. It was like, Oh, wow, man, this whole thing about land of the free, home of the . . . it’s, like, real—it’s going to happen, everyone’s getting to participate in it. But growing up, if you had ever told a black person from the hood you can be president, they’d be like, I could never . . . If you had told me that as a kid, I’d be like, Are you out of your mind? How?”
Jay tells Robinson that his mother knew he was dealing drugs as a teenager, “but we never really had those conversations. We just pretty much ignored it. But she knew. All the mothers knew. It sounds like ‘How could you let your son . . . ’ but I’m telling you, it was normal.”
Jay’s checkered past taught him a few things that he says will come in handy in his new role as a sports agent: “I know about budgets. I was a drug dealer,” he tells Robinson. “To be in a drug deal, you need to know what you can spend, what you need to re-up. Or if you want to start some sort of barbershop or car wash—those were the businesses back then. Things you can get in easily to get out of [that] life. At some point, you have to have an exit strategy, because your window is very small; you’re going to get locked up or you’re going to die.”
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