Sports figure(s) involved: Ronaldo Luís Nazário de Lima
Year: 2008

Be careful about picking up women in Brazil. Very careful. After a night at the club, Ronaldo took three transvestite prostitutes back to the crib and, upon finding out that they were male, allegedly offered each $600 to leave. One of the especially entrepreneurial hookers made a $30,000 counteroffer. When Ronaldo declined to barter over his potential humiliation, the prostitute leaked the story to the press. Not surprisingly, the Brazilian soccer star's engagement to Maria Beatriz Antony ended immediately after the scandal went public.