What are we drinking?

I was careful not to pick a drink that isn’t one of our sponsored beverages so I figured I’d go with a Tequila Avión margarita. And because it’s Cinco de Mayo this week!

You took over as President of Chicago Sport and Social Club back in 2001. What has been your favorite aspect of the job?

Really the satisfaction of so many people enjoying what we do. I go down to the beach on a Thursday night in the summer and there’s 4,000 people playing volleyball with smiles on their faces, leaving the stress of whatever happened at the office out of their mind completely. It’s pretty rewarding in that capacity. There aren’t many jobs where you really see the fruits of your labor and how it affects people and this is certainly one of them.

Do you play on any of the leagues?

I do bowling in the winter, softball in the spring and volleyball in the summer and I like all three of them. I played flag football last fall and realized that guys my age should not be playing flag football. I do the undercover boss thing and sometimes I actually sign up as an individual and go out and play on random teams just to see what the experience is like.

What is the funniest team name you’ve come across?

The team names crack me up. There’s every sexual innuendo that you could think of that comes up in these names. We don’t flag too many of them but sometimes you have to. Just like vanity license plates, people sometimes try to sneak through a plate that’s going to read different than how the letters look. Sometimes we’ll call people out or have to change the name. Every bodily function or sexual deviant you can think of becomes a team name.

You previously worked as a reporter for Fox News. What was your most memorable experience as a journalist?

The coolest thing that I got to work on was President Clinton’s impeachment. I was in D.C. the day Monica Lewinsky’s name was released. Word had gotten out that she was at this members-only club down the street and the entire national press corps went. It was three people thick along the fence lines with ladders, cameras in the air and live trucks. It was the first time anyone in the country was going to see her. For an on-going story that was the biggest story in the country, a president getting impeached mixed with my passion for politics that really kind of pulled it all together. And there was a little sex thrown in too so you can’t go wrong with that.

Do you hope to get back into politics one day?

My passion is politics. It’s funny, I’m not a sports fan at all. I like watching sports and of course that’s my business, that’s what I sell but when I got tickets to the Bulls game the other night people who don’t know me that well were like, “Oh, you must be so excited!” I’m like, “Uh yea, I like the hot dogs.” Politics is definitely an interest of mine more so than sports. I don’t know what I’ll do with that or if I’ll run for office some day but right now it’s just much more of a hobby.

Best advice you’ve been given?

To use a sports analogy, which I usually don’t but it’s probably the best advice I’ve been given, is to just keep your eye on the ball. Don’t lose sight of what the goal is. Sometimes you can get side tracked and start paying attention to the little things that don’t affect the business at the end of the day so you really need to stay focused on what the end goal is and what you’re trying to get to.

Do you have a favorite restaurant in the city?

I like restaurants off the beaten path typically. A place in Little Italy called Tufano’s is one of my go-to places. You never really see anyone you know there and the food is fantastic. It’s family owned so when you walk in they’re like, “Hey!” and it’s a very charismatic welcome.

Are you single?

I’m about as single as they come right now. I’ve been in several long-term relationships but for one reason or another they don’t work out. You know, I’m the best guy you’re ever going to meet so I would like to think it’s not my doing but who knows. Relationships aren’t easy.

How would you describe the dating scene in Chicago?

It’s a great dating city but it’s very incestuous. It’s hard to find someone who is out of the circle or doesn’t know someone you know. Sometimes it would be nice to just meet someone who doesn’t know you or doesn’t know your friends so you can get a clean slate and start from scratch but outside of picking up and moving out of Chicago I don’t know where to find that.

What neighborhood do you live in?

I’ve lived in Bucktown for eight years but I’m ready for a change, my place is for sale. I’m looking to move further East, closer to the lake. I don’t like high-rises, I like more space because I have a dog. I have a King Charles Cavalier Poodle, great dog.

That is not the kind of dog we would have expected.

It’s not one of those little ones, it’s not a toy. I want to clarify! Her name is Ruby. She’s not a big dog but she’s tough. She’s almost 20 pounds and she’s kind of a bad ass. She’s a lovable bad ass!

Last item you splurged on for yourself?

I lost about 18 pounds in the last couple of months and I realized that nothing in my wardrobe fit me so this past week has been an insane shopping spree for me. I have really bought an entire new wardrobe. I’m a clothes whore, I’ve been shopping like a mad man.

If you could choose one food to be calorie-free, what would you choose?

Chicago deep dish pizza. I grew up on Aurelio’s Pizza from the South side. It’s a medium crust so I love that it reminds me of my childhood. But Gino’s East’s deep dish pizza stuffed with cheese, sausage and pepperoni, I could eat that ’til there’s no tomorrow.

You’re stranded on a deserted island but can have one personal item, what are you bringing?

It would probably be a razor. I know it sounds stupid but I’m not a facial hair kinda guy and I would go crazy with the stubble and the beard.

If you could have a drink with anyone, who would it be?

Someone once asked if I was having a dinner party and could invite four guests who would they be and I think I picked Jimmy Fallon, Oprah Winfrey, Princess Diana and JFK Jr. You have politics, you have royalty, you have comedy and you have someone who has made a huge impact on society.

Photography by Neal Agustin