SPORT: Track and Field
COMPLEX SAYS: Tim Montgomery gained praise and fame by collecting a silver medal at the 1996 Summer Olympics in Atlanta and later winning gold at the 2000 Olympics in Sydney. He was also in a relationship with track star Marion Jones. However, by 2005 he was stripped of his medals after he was found to be using performance-enhancing drugs. Things got from bad to worse when he was was convicted of selling over 100 grams of heroin in the Virginia Beach area and sentenced to five years. Yeah, we'd be sporting' the screwface too if we lost all that in a matter of a few years.