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Phil de Picciotto plays caretaker for the most valuable property in all of women’s sports. That would be Anna Kournikova, the Russian-born tennis queen who this year should become the first $15 million-a-year jockette. He swears it’s not the easiest job in the world.

Everybody wants a piece of the comely Kournikova, from tournament directors to the suits on Madison Avenue. But to get to her, they now have to go through the Tysons Corner offices of Octagon Athlete Representation, the management giant of which de Picciotto is president. And these days, almost all suitors, including some with the deepest of pockets, are being turned away.

De Picciotto, though a New York native, has played the show-me-the-money game around these parts for a long time. After law school at Penn, he signed on with ProServ, the D.C.-based pioneer in athlete representation that was headed up by Donald Dell. In 1983, ProServ split up acrimoniously, and de Picciotto, then just 28 years old, co-founded another sportscentric agency, Advantage International. This fall, after some corporate takeovers and office shifts, Advantage was renamed Octagon. The company now boasts gross billings of approximately $1 billion for its clients, including the top talents in women’s tennis over the last decade: Steffi Graf and top-ranked Martina Hingis.

But for all his experience, de Picciotto’s never handled an athlete like Kournikova, for whom he thinks the prudent managerial advice is to reject many endorsement deals and service contracts. You might be surprised to learn that Kournikova, the biggest draw in tennis regardless of gender, has never won a tournament—she’s reached the finals of only two tournaments in her career, and lost them both.

Given that endorsement money is her bread and butter, it would seem likely that her agent would advise Kournikova to grab every dime that’s offered…now. De Picciotto doesn’t view Kournikova’s situation in those terms, however. Ever since he took over her management about a year ago, his duty, as he sees it, has been to help her get to a place where her forehand gets as much attention as her backside.

For the short term, that means restricting the public exposure of her name and face (and other body parts), no matter how many millions it costs.

“The money will be there for her,” de Picciotto says. “We have a plan that, over time, will make people realize that she’s a very good tennis player who happens to be exceptionally good-looking, and not just somebody who is exceptionally good-looking but her tennis doesn’t matter. There is something contrarian about our philosophy; it’s a less-is-more approach. But over the long haul, we feel that strategy will be more lucrative.”

The Octagon plan has already had Kournikova turning down seven-figure offers from more than one men’s magazine (de Picciotto wouldn’t get any more specific than “the obvious ones, the big ones”) to pose nude. De Picciotto has also shooed away a shoe company that wanted her to appear in a television commercial that, the company representative told de Picciotto, “would create the appearance” that she was playing tennis naked.

“My first question was, ‘You say you want to “create the appearance” that Anna is naked—so does that mean she’d have to be naked when you film it?’” de Picciotto recalls with a laugh. “And the answer was, ‘Well, yeah.’ So that wasn’t acceptable.”

The most ingenious of the high-dollar offers rejected by Kournikova’s representative came from a manufacturer who wanted the player to get a tattoo of its logo on her arm in exchange for millions of dollars. On the advice of counsel, she declined.

De Picciotto says the austerity plan wouldn’t have been necessary had Kournikova been better managed earlier in her career. She has been a known quantity since grammar school, when her family shipped her from Russia to Nick Bollettieri’s tennis factory in Bradenton, Fla. At the age of 9, she was signed by the Cleveland-based IMG, the biggest sports-marketing firm in the world (now best known for representing Tiger Woods). When Kournikova jumped from the junior circuit to the pro tour in 1995, at 14, she was prohibited from playing tournament tennis regularly because of rules put in place that year ostensibly to protect adolescent savants from burnout. According to de Picciotto, those rules had a very negative impact on Kournikova, from both tennis and image standpoints.

“She was the first name player impacted by the age limitations,” he says. “She was immediately very popular, and if she had been able to play in more tournaments, I think she may have been viewed much more from the beginning as a tennis player, because the articles would have been about her as a tennis player. But the inability to play gave her more time to pursue things outside of tennis—and gave writers the chance to write about her for things other than tennis.”

Kournikova’s relationship with Sergei Federov, the hockey star 12 years her senior and a fellow Russian, became favored fodder for journalists on the tennis beat. Federov picked up balls for her during a practice at Wimbledon two years ago, starting the rumors flying. Several months later, she returned the favor by attending Game 1 of the 1998 Stanley Cup final series between the Washington Capitals and Federov’s Detroit Red Wings, wearing what the Detroit Free Press described as “high heels and a pelt.”

Though she was still a minor when she returned to Wimbledon, the Sun, a London tabloid, gave Kournikova the space on Page 3 normally reserved for nudes of age. Other photo spreads, most notably one she did for Rolling Stone in red spikes and a red miniskirt that only partially concealed her panties, further Lolita-cized her image. Before long, her name or likeness or both were featured on more than 18,000 Web sites, many of which were pornographic. She had no financial stake in any of the sites.

“There were no restrictions on how Anna was presented to the public,” says de Picciotto of Kournikova’s days with IMG. “She didn’t even control her own name, as far as a Web address.”

The first sign that Kournikova was bumming about her public persona came during the 1998 U.S. Open, when she terminated her IMG contract and signed with what was then Advantage International. Federov, who like his gal pal was under contract to IMG (and had only recently been given a $28 million contract with an $18 million signing bonus—the largest in NHL history), also bolted to Advantage. De Picciotto would not comment on how his company had obtained Kournikova as a client, other than to deny that she and Federov had come as a package and to add that Advantage had paid a “negotiated settlement” with IMG to complete the transfer. IMG representatives did not return phone calls asking for comment on the defections.

“What we’re saying is that she is first and foremost an athlete, and that she desires professional success and excellence,” de Picciotto says. “The result of the untargeted focus on her before was that the athletic ability got lost in the mix. Her skills and desire were doubted.”

After taking over the reins, de Picciotto got control of the address kournikova.com and launched an official site, and he has begun going after the exploiters of his client on the Web. And, along with limiting new endorsements, de Picciotto has upped Kournikova’s asking price for those products she had already sanctioned. One industry source estimated that Kournikova’s relationship with Adidas alone could now bring her $10 million a year, making it the most lucrative apparel deal on the women’s tour. She’s also getting large coin from Berlei, a sports-bra maker, and Yonex, a racquet manufacturer. Her only major sponsorship deal with a nontennis company is with Charles Schwab, the investment firm.

Kournikova opened her 2000 campaign this week as the second seed in the Australian Women’s Hardcourt Championship but was knocked out in the quarterfinals by an unseeded unknown. Though de Picciotto won’t say so, Kournikova could do away with the need for an image makeover just by winning a tournament or two. Until she does, she will have to settle for the kind of attention she no longer seeks. The wire services recently reported that she had dumped Federov for another Russian hockey star. And on eBay Sunday, an autographed tennis ball from Kournikova failed to draw a single bidder. The Anna Kournikova Nipples Clock went for $15 that same day.—Dave McKenna