In recognition of the 20th anniversary of his run to the Wimbledon finals, this is the second of a two-part interview with American MaliVai Washington. Here, he speaks on the prospects of American men in the game and his current projects.

TW: You were part of one of the greatest generations of American men to play the game, with your peers Sampras, Andre Agassi, Jim Courier and Michael Chang winning Slams, and you and Todd Martin making Slam finals. What do you think can be done to turn the tide for American men right now?

MW: I don't have an answer for you. If there was an answer I think the USTA would've had it or spent the money to find it. Success at the top of the men's game is not something that comes easy. It's not something you just throw money at.

I think it's cyclical. We've seen over the years where Sweden is producing a lot of players, Spain is producing a lot, the U. S. is producing a lot of players. Right now Sweden is in that same downturn we're in. Outside of Rafa [Nadal], have there been any male players from Spain winning Slams in the last decade? And you can also talk about the women's game: Where are the ones from Sweden? Every country is trying to achieve the same thing. Why did Djokovic break out of a small country? If you're going to pick a country that would have a Grand Slam champion, you're probably not going to pick Serbia!

I don't have an answer on what it's going to take. Actually, Taylor Dent told me this: Trying to produce a Grand Slam champion is like catching lightning in a bottle. It's tough. You have to have a good talent pool, you have to have someone with the work ethic and the God-given ability, and you put it all together and you might—might—produce a Grand Slam champion.

On the men's side, the last 10 years, how many different Grand Slam champions have there been? It's that difficult. And to think Switzerland has had Stan [Wawrinka] and Roger [Federer] in that list in the last decade is phenomenal.

It takes a lot of hard work and a lot of dedication, and a big talent pool.

TW: And what do you think about college as an option for development, for others and for yourself as a young player?

MW: I don't think you can ever just pick a group of players and say we're all going pro. I'll use my personal example: I turned 18 and went to the University of Michigan and when I chose to go to Michigan, Pete Sampras, Jim Courier, and Michael Chang all chose to forego college and turn pro. In fact, some of them turned pro before the end of high school. And those were my peers growing up. From 12 and unders all the way to the 18s, and in junior tennis, I beat Michael Chang, and I beat Andre Agassi. But if I jumped on that bandwagon of turning pro, too, it would've been a disastrous decision for me. I needed to develop emotionally and physically, and my game needed to develop when I was 18, and college tennis allowed me to do that.

One year in college wouldn't have been enough for me. Three years in college would've been one year too long. After my sophomore year, having finished No. 1 and having some modest success on the tour, having beaten some players in the top 100, top 200 and winning a Challenger in 1989…things like that started telling me now was the time.

It's such an individual decision for a player to turn pro, and it has to be a decision that player feels comfortable with. It can't be their agent or the parents pushing them to turn. Certainly, they can have influence, but that player has to be comfortable with that decision to turn pro.

TW: It’s evident education is something you believe strongly in, particularly with your work through the MaliVai Washington Youth Foundation. How difficult was it to start that during your playing years?

MW: We started it in 1994, and it was literally on paper and there were no programs that we were running at the time. And toward the end of my career in 1997 is when we really started creating programs and ideas about what we wanted to achieve.

And at that time, my current executive director, Terri Florio, and I had ideas about what we wanted to do. And I certainly didn't have the expertise as a touring tennis professional on how to run and start a foundation. I wasn't trained in that skill, but she had that expertise and I think I had some ideas on what I wanted to do. I didn't even have fully developed ideas. But I know I wanted to introduce the sport of tennis to young people, that group of kids who otherwise wouldn't have the opportunity.

And the two of us, we put our heads together and started creating partnerships with the Boys and Girls clubs of northeast Florida and started tennis programs, and then progressed into after-school homework programs. And now we're 20 years into it, running programs.

It would've been difficult to be a part of the foundation [full-on] while I was on the tour. We started it then but we didn't have any programs. Knowing the amount of time I put into it now, I wouldn't have been able to put in that time while I was on tour.

TW: And now you’re doing real estate work now through your firm, Diamond Life Real Estate. How did that come about?

MW: I say it's my second love. I always loved tennis and from being a kid, I remember being fascinated by real estate. Knowing that tennis is something I've been involved in since I was five years old, I knew and still know today that tennis is something I'll be engaged in for the rest of my life in some way.

But I always had a desire when I left the tour to also be engaged in something that had nothing to do with tennis. I didn't have a big desire to get back out on the road 25 weeks a year to coach. That would've been tough for me. And what I realized soon after that, actually while I was injured, real estate allows me to be involved in something I love to do that has nothing to do with tennis. It's so fascinating to me.

And most people don't know this: I was recovering from my first knee injury in the spring of 1997, and one day I was literally looking in the classified ads and looking at real estate. And there was an ad in there for a real estate class. Knowing that I was going to be rehabbing for, it turns out, the next eight months, I said, “You know what, maybe I'll take a real estate class!” So I literally called them up at that moment and said, “Hey I see you have a real estate class, can I sign up for it?” She was like, “Well, the class started today and you can't miss too much of it, but if you come in this afternoon, you'll be fine.” I was like, “Cool.”

So I signed up right then on the phone and as it turns out, I realized the first couple of hours there that this was the class to get your license. So I was like, “Maybe I'll get my license!” It was a crash course, seven days, knocked it out—I didn't have anything else to do but rehab. I'd get my rehab in either early morning or late in the evening, and in the middle of the day for this week, I was sitting in real estate class.

It's kind of funny how it happened!

TW: That is an interesting turn! Coming back to Wimbledon, this year any picks?

MW: It's hard to pick against Serena [Williams] and Djokovic. I think if someone wants to pick a dark horse, they can. But those are the two best players in the world:  Djokovic by far on any surface right now, and with Serena, certainly the best player in the world who has had some misfortune in the last three majors. But with her game and her power, I think this year it's going to be her most likely major to win.

I know I really went out on a limb picking Serena and Djokovic!