Sheryl, Mike’s wife of eight years, manages Matthew and the household so Wilbon can maintain his manic travels from games to TV studios, from DC to New York to Scottsdale. A DC native, Sheryl has an undergraduate degree from the University of Virginia and a law degree from Duke.
Just to see the Cubs?
Yep. I took my father-in-law to Wrigley Field. My father-in-law’s a Washingtonian. He is a knowledgeable observer of sports. Redskins season-ticket holder, the whole thing. I said, “You haven’t been to Wrigley Field?” So I’m still connected with my Chicago teams.
Which are you most tied to?
I’m most tied to the Bulls now. Two months ago I was most tied to the Bears. You know what I’m doing in March? I’m going to Arizona because the Cubs will be in spring training.
Do you have that same cracked-out feeling about the local teams? Redskins?
I have no rooting interest in any of the local teams. I kind of root for all the colleges. I love it when Georgetown and Maryland and George Mason do well.
Talk about the other guy from the Windy City. When did you first meet Barack Obama?
We met in 2004. I was writing a book with Charles Barkley. Charles wanted to do a book on race and how people saw race in America, and Barack is one of the people we wanted to talk to.
At that point, he was in the Senate?
US Senate. We hung out with him for the better part of the day. We walk out of Barack’s office, we go to the car, and Charles and I look at each other across the hood of the car. I don’t know who spoke first. We just said, “Can you believe this guy?” Neither one of us had ever seen anyone like him up close and personal.
In what sense?
He was just impressive. The way he can inspire you to feel something. Sort of the call to action, the call to be encouraged. I came back home and told my wife, “This guy’s going to be president.”
You said that?
At the time, the notion of some unknown black man from South Side Chicago winning the presidency was unthinkable, but I just thought, this guy, he can appeal to people. I knew the whole story, his interracial parentage and where he was from. We had some people in common.
I went to Northwestern, where his brother-in-law, Craig, was assistant coach. And Craig grew up on the South Side at the same time as my brother, Don, and I did. Craig and my brother played basketball with and against each other.
Did you see Obama in Chicago before he ran for president?
We used to run into each other at restaurants like Japonais in Chicago. We’ve run into each other a couple of times.
Do you hang with the President?
I’m not some insider. He called me when Matthew was born. He called when he heard I’d had a heart attack. It was during the presidential primaries. He called to get on me about not being able to go to any more rib houses in Chicago after having a heart attack—which was very kind of him.
It seems like that’s the kind of human being he is—a normal guy. He likes to be in the NCAA pool. Our conversations have often been about “Who’s left in your pool—your bracket as dead as mine is?” It’s not that he’s a sports fan, but he’s rooted in sports, rooted in basketball. Basketball is a metaphor for much of his life, like the Democratic process. And so we share that.
Have you been to the White House?
I don’t expect to see him at all in Washington. I may never see him as president.
You might find yourself invited to a state dinner.
I doubt it. I’m not in that circle. I don’t crave it, you know? Most people in the White House—not him—most people in politics look at sports people as trash. They look at us as secondary people.
I’m not sure that’s accurate.
Sure it is. People in the media—people in my own newsroom think we’re second-class journalists.
Hard to believe. You’re probably the highest-paid journalist at the Post. Back to sports: Your take on the Redskins?
They’re stuck in this sort of land of mediocrity.
Most teams are stuck in that area. The Redskins suffered for many years due to management. They spend a lot of money, not all of it wisely.
What’s your estimation of Dan Snyder as an owner?
He’s brilliant in terms of business and is incredibly seasoned and as successful as any owner in the league. He’s already tied for number-one owner when it comes to making money—and putting it back in the franchise. Snyder does that.
How would you rank him as an owner able to establish a winning team?
On a one-to-ten scale, he only gets a five—four or five. They’ve been to the playoffs a couple of times. They’re not Detroit—not that terrible. They’re just not really good. So he’s a middle-of-the-pack guy, just like a bunch of others.