Anna Kournikova – Adidas, Estimated $50 Million

Big brands usually book gold medalists and star athletes as their endorses. In the case of Anna Kournikova, she was very lucky. The Russian tennis player managed to become one of Adidas’ ambassadors despite not winning any singles title (though in 2000, she was ranked 8th in the world). To get the whole $50 million, she had to start winning. Sadly, she just couldn’t win and the money that she got from the brand was only $3 million. While that may be a small amount of money for celebs, it’s a generous size for ordinary mortals with mortgage issues.