Off the court, Ms. Kournikova is the highest paid female tennis player in terms of endorsements, licensing and sponsorships. In fact, she takes the top earnings seed among all female athletes.
She has an estimated $15 million in business deals with the likes of Adidas, Berlei, Goshen, Pegaso and Yonex. If some names don't sound familiar to Americans, that's by design.
"We're taking a global approach," says Phil de Picciotto, president of the athlete representation division of Octagon, which represents Ms. Kournikova.
Such Asian brands as Yonex and Goshen supply her tennis equipment. Her telecommunications partner is Mexican company Pegaso. She has clothing deals with Germany's Adidas and the U.K.'s Courtalds Textiles' Berlei.
In 1998, Ms. Kournikova and her family turned to Octagon for career management, which includes marketing, legal and financial planning.
"From the very beginning, we created a plan with Anna and her family that had a lot of strategic elements," says Mr. de Picciotto, 45. "It's long-term, quality over quantity, lifestyle-related product and service affiliations."
Octagon also assisted Ms. Kournikova in an area where she was already adept -- covering the net. The company struck a deal for Ms. Kournikova to take a stake in AthletesDirect, the Web company that manages her site.