Name: Dr. Stephen Cito
When: 1996
Sport: High School Football

When you're doing your best to win, sometimes it's in your best interest to pull out all the stops. Sane people call this "cheating." Complete assholes call it "gamesmanship." Jerry Rice used stickum, Ray Lewis used deer antler spray, and Dr. Stephen Cito (emphasis on "doctor") sharpened his son's chin-strap in an effort to literally slash the competition. After one two three four five kids left a single game due to lacerations (with one later going to the hospital for a dozen stitches), officials stopped the action to investigate, and found out the young Cito's helmet was "sharp enough to shred a magazine cover." For failing to stop his crazy dad, the younger Cito was expelled from his high school. For being a crazy dad, Cito was given a weekend in prison, a year on probation and 400 hours of community service. Afterward he was free to resume his life as a children's dentist.