Year: 1996

Despite having been married since 1957, Sterling has been a widely-acknowledged (and very public) philanderer during his time owning the Clippers. In 1996, one of his former ladies brought a suit against him, and while under oath cited numerous examples of horrifying behavior from Sterling.

Among them: Sterling groped her on numerous occasions in a way that made her feel “uncomfortable,” he requested that she visit his friends and have sex with them, and he enlisted her to find massage therapists who might offer the happiest of endings, or as Sterling said, "I want someone who will, you know, let me put it in or who [will] suck on it."

Yikes.