On March 23, 1995, Moss backed a friend in a hallway fight against a white student who had allegedly used racist comments towards Randy's friend. Moss was initially charged with a felony for kicking the student, but it was later reduced to a misdemeanor.
On August 1, 1995, Moss pled guilty to two counts of misdemeanor battery and was sentenced to 30 days behind bars at the South Central Regional Jail in Charleston, West Virginia. He served 3 days in jail starting that night and would be required to serve the remaining 27 days within the following 18 months, after he completed his freshman year in college. Moss was expelled from DuPont and completed his education at Cabell Alternative School.
After originally signing a letter of intent to play college football with Notre Dame in 1995, Moss took part in a racially charged fight at his high school that left one person hospitalized. Notre Dame subsequently denied his enrollment application
In 1996, while serving his 30-day jail sentence in a work-release program from 1995, Moss tested positive for smoking marijuana, thus violating his probation, and was dismissed from Florida State. He served an additional 60 days in jail for the probation violation