Except for Muhammad Ali and George Foreman, no modern athlete has made a more radical image transformation than John McEnroe. He was once an arrogant, irascible tennis prodigy whom parents implored their kids not to emulate, even as he played with an intellectual approach and ascended to number one in the world. Today, at age 49, he's a self-deprecating, unsparingly honest tennis commentator for NBC and a host of other networks, and the only person with the chops – not to mention the balls – to campaign for the as-yet-uncreated job of commissioner of tennis.

Prodigy, for once, is no overstatement. For those too young to remember, McEnroe reached the semis at Wimbledon in 1977. He was 18. In '79 he won the U.S. Open, and two years later, Wimbledon. His creative shot-making and fiery outbursts led people to think of him as an artist and a genius, and his epic matches with Björn Borg, Jimmy Connors, and Ivan Lendl got Americans excited about tennis. He won seven grand-slam singles titles and was number one in the world from 1981 to '84, but by 1986 he'd lost a step, took a break, and married another prodigy, actress Tatum O'Neal. The time away wasn't supposed to be the end of his career, but it turned out to be the beginning of the end. He never won another grand slam and seemed to lose his Midas touch.

McEnroe had short, unsuccessful stints as captain of America's Davis Cup team and as a TV talk show host, and he and O'Neal divorced in 1992. He's now in an 11-year marriage to Patty Smyth, the lead singer of Scandal, and raising five kids from his two marriages, plus one from Smyth's previous marriage. He's also playing seniors tennis and dealing art. (He recently sold an Andy Warhol portrait of him and O'Neal at auction for about $475,000 and gave the proceeds to Habitat for Humanity.)

Our interview took place in his downtown Manhattan gallery amid pieces by Warhol and Jean-Michel Basquiat. McEnroe is great company, a guy's guy, but he also struck me as a lion in repose, as if talking tennis and playing it on the seniors tour aren't quite enough to quench his hunger for adrenaline and success.

Was Rafael Nadal beating Roger Federer at Wimbledon really the best match you've ever seen?
John McEnroe: Actually, it was. The way it ended: 9–7, and they couldn't have played another game [because it was almost 9:30 pm in London]… There was just some unbelievable tennis. The fact that they'd had two rain delays. The fact that it looked over a couple of times. It's not often where you sort of switch allegiances mid-match, where you're pulling for one guy, then you start pulling for another guy. To be able to be in that commentators' box was awesome. I could definitely relate to what was going on there because it brought back some memories. There are a lot of similarities, for me at least, to what Björn Borg and I went through at Wimbledon. It really was a match for the ages and a changing of the guard and a changing of the game.

Is Nadal number one on the planet now?
Yep. He's definitely the number one player in the world. It's not official, it won't show up on the rankings for a little while, but it's gonna happen in the next couple of months.

One of the most dramatic moments of the whole telecast was after the match, when you interviewed Federer in the hallway, asked him, like, two questions, and then just ended the interview and gave him a hug. Why'd you do that?
He was crying, and I felt like he needed something besides another question. I could feel him losing it. I wanted him to get the feeling of respect that we all had for him. I could definitely relate to him, to a devastating loss like that after giving so much. I mean, the guy dug deeper than he's ever dug, and he didn't win. I could see it with the first question. For the second, I could see, he was just on autopilot. I could feel him welling up and losing it, so it just seemed like the thing to do. In most cases in those post-match interviews, you don't get a whole lot, but every now and then you get a sense of the individual. You lose sight, when what you see on the court is so great, that these guys are human beings. And I know that somewhere in the back of his mind, a small part of him is wondering, Is this the beginning of the end? He'd never tell you that, but he's a student of history. He knows how it goes. Somewhere deep down he's wondering, Is this where I lose my dominance? And that's not something you ever want to confront.

I've been having this argument a lot lately: Who's the best player of all time? Is it Federer, Pete Sampras, or Rod Laver? Those are the only three names in the conversation, right?
Yeah, those three. Laver has won two grand slams and was my childhood idol. But he's smaller, 5-foot-9, and times have changed. Could he handle a guy like Sampras at Wimbledon? I don't think he could. Personally, I idolize Laver, so I would never put anyone in front of him, because he was left-handed, and I just love the way he played. I tried to play like him when I was a kid.

What about the modern era: Sampras or Federer?
Roger's serve isn't as big a weapon as Pete's. Even though Pete's movement was underrated, the way Roger moves is more like a ballet dancer. Roger's forehand is more of a flowing shot, more of a beautiful shot. Pete's was like a hammer. But if you asked me who was better – say, if they played 10 times on grass – I would pick Pete over Roger, like, 6–4.

The crop of Americans we have out there right now is good, but not world-beaters like we've become used to. Andy Roddick's a top ten player, but you don't expect him to get past top guys like Federer or Nadal at the U.S. Open.
Andy to me always has a puncher's chance. He's like George Foreman when he beat Michael Moorer with one punch. You can never count Andy out. I always looked at him as a smart kid and a likable personality. He's got a harder serve than anyone who has ever served. He may not be as good a server as Sampras – he doesn't place the ball as well and he doesn't do as much with it and he doesn't back it up with as good a volley – but nonetheless it's a massive serve, and he has a huge forehand. He finished number one in the world in 2003, which is quite an accomplishment. He's been in two Wimbledon finals, and he won the U.S. Open. So, he was a little unfortunate, maybe more than a little, when Federer came along as he was playing his best tennis.

The other big American now is James Blake, and sometimes I think his career has been disappointing. He's also in the top ten in the world, but he's never gotten past the quarters in the majors.
Well, I don't think it's disappointing. It depends on what your expectations are. It seems to me he's got one plan, and that's hit it as hard as he can. It's like the guy who throws the fastball by you. There's not really a Plan B.

Nadal is amazing to watch. His physical ability to run and make shots while he's three feet wide of the court, to make a crazy angle and get back in position is unlike anyone I've ever seen.
Borg was like that. People forget.

But Borg didn't have the mobility that Nadal does.
Yeah, he did. I disagree. He was faster than Nadal. He wasn't as strong, but you're talking about a guy who ran a 100-yard dash in 9.6. You're talking about one of the fastest individuals ever on a tennis court. He didn't hit the ball as hard, but try hitting the ball hard with the racket he used – a wood racket strung at 90 pounds. Nadal wouldn't be hitting those shots with that racket; it was a different time. I pick up these rackets of these other guys, like Nadal; he's using a racket that is 30 to 40 grams lighter than the one I used. Federer's is 20 to 30 grams lighter. So that's the trend. And the racket speed is incredible. I don't know if you follow baseball, but when Willie Mays and Mickey Mantle played, they had 38-ounce bats, and people thought you had to have a heavier bat. Now they see a Barry Bonds with lighter bats [between 32 and 33 ounces]. So it's about bat speed. In the old days, if you told Mickey Mantle that he needed to go from a 37-ounce to a 31-ounce bat he would have looked at you and said, "You're full of you know what."

You had some amazing battles with Björn, but now you guys are friends, right?
Yeah, we're friends on and off the court. He's my buddy. I don't see him that often, but he's an incredibly nice guy, great to talk to, would give you the shirt off his back.

What would young McEnroe the player think about McEnroe the commentator?
When I was 25, if you'd have said I was going to be a commentator, that would seem like, "Oh, my God. That's a huge step down." And I didn't realize it would allow me to show a side of my personality that I felt was always there: that I wasn't always a person who took myself so seriously, that I was able to show some self-deprecation, yet I had a knowledge of the game.

In your day there were a lot of guys who were serve-and-volleyers, guys who made their living in front of the service line. Now barely anyone serves and volleys. Why is that?

For a number of reasons. It's become intimidating because people hit the ball harder than ever. And if you look at a guy like Nadal, the spin he puts on the ball is wicked and his pace is phenomenal, and the comfort level to come in to the net against guys like him is just not there. Against him you don't really have enough time to volley. Another reason is it's not taught at a junior level, so if you're not taught the technique as a kid, you're not going to feel comfortable trying to figure that out as you get older. When I was growing up it was considered something that almost every player would do. Now, ironically, I watched the doubles finals, and some of these guys are serving and staying back, which is laughable. That used to be, like, against the law.

When did you start to serve and volley?
I didn't serve and volley until I got to Wimbledon in '77.

Really?
When I was in the 18s [junior tennis] I was a clay court player. The only tournaments I won were on clay, and then I went to Wimbledon. I had enough points to get into the qualifying tournament, but I saw that the courts were faster and I felt like I was strong enough to make the quick moves required to cover balls like passing shots, and my fitness level had improved, so that's the first time I did it. And I made it to the semis. I lost to Jimmy Connors. My personality is to attack, to put pressure on the opponent.

That's interesting, because you had an aggressive serve and aggressive volleys but not aggressive ground strokes.
Well, I was aggressive in the sense that I was looking for ways to use the geometry of the court to go from a defensive or baseline position as soon as possible.

For players who are reading this, can you break down what we're talking about with the court geometry?
From the baseline in, imagine different areas of the court where you could find an angle and get to a position where you could take advantage of a person being off-balance. The farther you get back behind the baseline, the more difficult it is to do that on one shot. If you get 10 feet behind the baseline, you can't just charge the net. If you're at the baseline, you could do it with one shot. I'm trying to create that constant feeling of uneasiness, which is what Pete Sampras was so good at – being able to not allow you to relax. And I would use a racket that was more like a slingshot, in a sense. As opposed to the guys that take huge swings, I would use their power. That's why my swings were shorter, because I felt like the best way to take advantage of what they were doing to me was simply to take advantage of it and to use their pace to my advantage. It got more difficult, and I became unsuccessful at it later on in my career because I lost half a step, and you lose some of that confidence.

You talk about geometry in terms of the hyperintellectual player, and yet we've seen you be so emotional. When you were angry out on the court, were you out of control or in control?
I was in control most of the time. I think later in my career I became more out of control. I always thought I was borderline arrogant, but I wasn't saying anything obscene, so I think I was in control.

Were you trying to throw off your opponent?
My feeling was that if you reach the professional level, you're a professional, and you have to deal with certain things. If you're saying it's ruining my concentration, you don't deserve to be out there, as far as I'm concerned. So I wasn't deliberately thinking, All right, I'm gonna get this guy. I'm gonna stall for a minute. I was legitimately upset; I felt that I had been shortchanged. If I go up to the umpire and I say, "Fuck you," what are the odds of that umpire, the next time around, giving me a call? I would say that he would want to screw me because I just said "Fuck you" to him, right? So if a player would interpret what I was doing as intimidating an umpire, I would kind of laugh that off, because I was willing to lose four, six, or seven points to say what I really believed and win anyway.

Is there a weird thing going on in the locker room in tennis? I mean, you're in there with a bunch of guys who aren't on your team – nobody's on your team.
I always thought it would be better if we were separate, like boxers, and Connors, I'm sure, would agree. So you could build up this sort of energy, like whatever you need to sort of get that edge. And it is weird when, like, Nadal and Federer are right next to each other in the locker room – "Hey, how you doing?" – and then you go out and play and it's a different thing. It's unusual. You don't have that in other sports. You're just sort of all in one room and then you're playing. It doesn't make sense in a way, but it's just the way it is.

A lot of guys like to debate where women would be if they played on the men's tour. Let's take Serena, playing at her hottest, and put her on the men's tour for a year. Where would she be? Top 10, top 20, top 100?
I would say if she played a full year of just men's tennis, it would be tough for her to win matches. I'd say she'd be around 500th in the world.

That low?
The less she played the better off she'd be to beat people.

Let's send her to four majors. Can she get to the quarters?
No.

What about Steffi Graf at her best?
Whoever. You name it.

She can't make it to the third round?
That's my opinion. Now, if you set up one match, and she's gonna play a guy ranked 100, 200, 300, or whatever, then there's a possibility, because Serena Williams has been in way more high-pressure situations, more than a guy who's ranked 100 or 200. So that guy could fold. But there are also juniors out there who hit the ball harder than Serena Williams. Kids who are 18 who you've never heard of would beat Serena Williams on a given day. But of all the sports, one of the only ones that gives out equal prize money is tennis. If you would have asked me 25 years ago, I would have said it would be a bunch of baloney that it's even considered. The disparity was so great. And the other argument is that men play best-of-five sets and women play best-of-three. But just because a movie takes three hours doesn't necessarily mean it's better than the hour-and-a-half movie. I mean, we're setting such a great example. Where else are women being treated equally? Very few places. That's like saying, "Where are blacks being treated equally?" So as a somewhat more mature person at this stage in my life I see what that means, and what Billie Jean King represented.

You grew up in New York, so what's your team: the Yankees or the Mets?
I was a Yankee fan until 1981. That was the year the Yankees were two up on the Dodgers and lost four straight. And George Steinbrenner apologized to the city. He said it was embarrassing. I remember the headlines. I lost in the Wimbledon finals around that time, and I thought, Listen, it's a hell of a lot better than the Mets. They're lucky if they're .500. Look at all the teams that don't even make the play-offs. And taking a crap on the team that just made it to the World Series just seemed lame. Really lame. I was disgusted personally because I knew how difficult it was to get to a final or a World Series. So right then I switched allegiances. That's when I switched from a Yankees fan to a Mets fan. That was the moment.

And you're still a Mets fan?
Sadly, I'm still a Mets fan.

How did you get into art?
Well, Vitas Gerulaitis [a top ten American player from the '80s] was responsible for that one. You get a little money, and you get a house and a car and music equipment. But he was always, "Hey, let's go to SoHo and just sort of check that out." That's where it originated. Also, I relate to artists in a way. The greatest compliment I ever got was when people called me an artist, and I understand that solo aspect of being an artist, when you're in there by yourself, trying to do something great, and people who don't even know you can come up and just dump on you. But also, just being by yourself like in tennis. From that standpoint I do take a lot of pleasure in being around art as opposed to, "Oh, uh, my GE stock went up a little bit."

So how did you go from being this angry man to supernice guy?
Well, I don't know about supernice guy. The irony is that when I play senior's tennis, and I don't go to an umpire and say, "Fuck you," people are like, "Oh, my God."

In the past you said you want to be the commissioner of tennis. It's a position that doesn't currently exist, but a lot of people think that's a good idea. Do you still want that?
I'd like to be the commissioner of tennis, but do I want to get into politics? Sometimes I have delusions of grandeur that that would be an interesting, good thing. I'm talking about actual politics, like being a congressman, but then I see how unbelievably nasty it really is, and maybe I'm not quite knowledgeable enough to actually do it.

It seems to me like mayor of New York City is a job that you could get.
I don't think so. See, when I actually sit and think about it, I think maybe I better stick to commissioner of tennis. [Laughs] It sounds good on paper. But the reality is that the reason I even think about these things is only because, all in all, I've been pretty lucky.

At this point in your life are you a little bored? Thinking, What am I going to do next?
[Long silence] Yeah, yeah. I am. But I find comfort in the fact that I'm able to look at the bigger picture, and I realize that most people have it a whole lot worse than I do. So when I get my perspective in order, I realize, Hey, don't force it. Let's be careful what we ask for.

Do you ever find yourself getting mad at your kids the way we used to see you get mad at the umpires: "You cannot be serious! I told you not to do that! What's wrong with you?"
Yeah. I think that happens. I don't use that same phrase, because I think that would be a little too obvious. I save that for the commercials. But, yes, it's a loud dinner table.

Do you still pick up the guitar every once in a while?
Yeah, I do. It makes me appreciate my tennis more. [Laughs]

Who are you going to vote for?
I'm going to vote for Obama. I'm going for the change. I like John McCain, or he seems like a cool guy in a lot of ways. I don't agree with a lot of his policies, but he still seems like a cool guy. To me Obama would be a much better thing for our country. I'll be pretty into it just to see how it pans out.

What is that one thing are you most proud of from your tennis career?
The best thing I ever did was when I was offered a million dollars to go play in South Africa and didn't take it. I was 21 years old, and part of it was like, Well, if they're offering me this obscene amount of money just to play one match, there must be something really wrong. Many years later, after Mandela became president, I was sitting in his house in Johannesburg. I'd brought my racket, the wooden racket I played with at Wimbledon, and I gave him that racket, and he held it. He had big hands, and he held it like he had played before, he held it the right way, and he seemed happy to have it. He seemed like he had no bitterness toward white people or the people who had imprisoned him for the better part of 30 years, and I thought, God, I'm pissed off at some guy if he, ya know…

Blows a call.
Yeah. Exactly. And this guy had this incredible aura about him, more than any other person I've ever met. I was there with a couple of guys – Yannick Noah, Björn Borg – and my wife, and I happened to be sitting right next to Mandela, and he says, "I've got to say, it's an honor to meet you." He says that to me, right? I thought, Oh, if I had a fucking tape recorder! That Nelson Mandela said that it was an honor to meet me! The memory of that was worth a million. Way more than that. That would have been the greatest thing anytime anybody ever said anything, right? I remember just thinking at the time: I just wish I could play this for all those assholes who said I was a jerk. [Laughs]