You made it to last year's U.S. Open final. Do you have one more fairy-tale run in you?
I don't know what's in there. But I've spent a good portion of my career feeling that way and overcoming my own questions. There's nothing this year to suggest I have a high level of tennis in me, which has been frustrating. That being said, New York is going to be very comfortable for me. I'm either going to win the last match I play or make somebody beat me.
Do you agree with those who have said you used to be a punk?
I still spend many days being a punk, to be honest. But I've basically grown up. And when I look at myself 20 years ago, I understand that person a heck of a lot more than I want to be that person.
When you see a picture from your past — tie-dye shirts, denim, the mullet — do you cringe?
It's hard to get me to see it, because I would never look. And if I did get my hands on it, it would probably hit the fireplace.
Your dad Mike worked your game hard when you were growing up. What's your advice to parents who may be pushing their kids too much?
I would caution against categorizing it as advice because you have to understand somebody's circumstances to direct it to them. What I will say is that, in my experience, the healthiest thing you can do as a parent is to define what success is to you. And hopefully that conclusion won't be a result inside the playing fields of any sport.
Your kids Jaden, 4, and Jaz Elle, 2 may have the best tennis genes ever. Do you feel pressure to nudge them into tennis?
You haven't met the rest of my family. So let's not necessarily conclude that they have the best genes. But if either one chose tennis, I would marvel at their grit and ultimately have to respect that. And I would have to take a deep breath.
There no new American tennis players that people are excited about. What is going on?
We've come through an amazing few generations of American tennis champions, all the way back to Stan Smith, to John McEnroe and Jimmy Connors, to Pete [Sampras] and myself. It's a standard that's a bit unrealistic as far as continuing generation after generation. That being said, we do have 290 million people to choose from.
At the start of your courtship of Steffi, you spied on her and even recruited a ferry operator to report on her whereabouts. How did she get over the fact that you were a stalker?
I sort of fed her that information piece by piece. I waited till the roots were deep before I exposed the depths of my capabilities.
Who wears the pants, you or Steffi?
Well, she looks better in pants than I do. It's a nice mixture for us. We both like to be busy. We both like to make sure the people around us are more comfortable than we are. I tend to take more chances, and she keeps things very grounded. I tend to second-guess my own eyes — whatever I see I question. She has a lot of clarity and trust in her instincts. I don't trust my instincts.
You built a charter school in Las Vegas. Have you given any thought to teaching?
School isn't my wheelhouse of strengths. I was an 8th-grade dropout, though I finished with correspondence classes. When I walk through the classrooms at my school, I try to figure out what the classroom's grade is. I listen to the questions and try to answer them. When I get to a point where I can't answer the questions, I'm somewhere around the fourth grade.
If you could take back one thing from your past, what would it be?
Not seeing Frank Sinatra.
Frank Sinatra?
I had the opportunity to see him in 1990. It's almost sacrilegious to say this — at the time, I was like, "Why would I go see Frank Sinatra?" Listen, I can sit here and give you a list of things I wish would never have happened. At the end of day, the obstacles end up becoming your foundation, and that's a treasure. Why would I give that up?