From Boston sports blogger to chopping it up with the President of the United States—say what you want about Bill Simmons, but he’s the perfect example of anything being possible.

Simmons has his hands in everything these days, stepping away from his podcasts and HBO dealings to sit down with Barack Obama for GQ.

There were definitely some high points, so let's check out a few:

“It’s really aggravating not having you on Grantland,” he said, almost like I betrayed him. “I go to the site and there’s no Simmons. Come on, man, it’s not the same.”

You’re out to dinner with your wife and the phone rings. How many of the people in your life are you like, “Uh-oh, I’ve got to take this”?
Malia and Sasha. [laughs] And maybe my mother-in-law. My national security adviser, Susan Rice, and Denis McDonough, my chief of staff. Those are the only people whose call I would take during a date night with Michelle.

What’s the most entertaining conspiracy theory you ever read about yourself?
That military exercises we were doing in Texas were designed to begin martial law so that I could usurp the Constitution and stay in power longer. Anybody who thinks I could get away with telling Michelle I’m going to be president any longer than eight years does not know my wife.

Is it true you have a virtual driving range in the White House?

Has anyone come to the White House and picked up your older daughter for a date?
No, but I’ve seen some folks glancing at her in ways that made me not happy.

Does it scare you that your wife could have a billion-dollar daytime talk show and you could be Stedman 2.0?
[laughs] Uh…

Because that’s in play. She could do that if she wanted.
And if that’s what she wants to do, I’m okay with her making a whole lot of money. There’s nothing wrong with that.

Would you ever want to be part of the ownership for an NBA team?

Would it have to be the Bulls, or would it have to be somebody else?
Well, you know, I know [Jerry] Reinsdorf pretty good—he’s not giving that thing up anytime soon. But I have fantasized about being able to put together a team and how much fun that would be. I think it’d be terrific.

I had to ask you one thing you can’t answer! Here’s one you have to answer: Who’s more untradable, Derrick Rose or Jay Cutler?
[pause] Oh, I think Rose still has more upside. Remember, Rose is still awfully young.

So you haven’t given up on Rose?
I’ve not given up on him. Sadly, I think it’s hard to imagine, after that many injuries, him getting back to his MVP-season performance. But he can still be a top-ten point guard.

By Glenn Erby


Low price, available in multiple styles and colors!