[3] His best season was in 1988, when he intercepted 4 passes and recovered 2 fumbles, helping Cincinnati reach the Super Bowl.
Towards the game's conclusion, Montana threw a 10-yard touchdown pass to John Taylor to give San Francisco a 20–16 lead with 34 seconds left.
In May 1987, Billups was arrested in Hamilton County, Ohio and charged with felony domestic battery for beating his then-girlfriend, a Cincinnati resident named Tracy Fair, after she ended their relationship.
[4] In January 1990, Billups was arrested in Hamilton County, Ohio and charged with the unlawful possession of a concealed firearm, the unlawful transportation of a firearm in a vehicle while committing a crime, and two counts of aggravated menacing after pointing a .38 caliber pistol at two undercover police officers.
In March 1993, Billups was arrested by FBI agents in Fayette County, Kentucky and charged with making terroristic threats against Washington Bullets basketball player Rex Chapman, whose sister, Jenny Chapman, Billups had been dating and allegedly abusing.
[4] Billups pleaded guilty to the charge in June 1993 after accepting a plea deal, and he was sentenced to serve twelve months in the federal USP Atlanta, three years of supervised release, and he was fined $10,000.
[9] This case prompted multiple women to come forward and accuse Billups of sexually assaulting them in similar fashions, but no additional charges were filed.
[6] Billups accepted a plea deal that reduced his charges to only one count of criminal conspiracy, and he was sentenced to serve three years of probation, which would begin following his release from the Atlanta federal penitentiary on April 4, 1994.
Driving at speeds in excess of 100 mph, he lost control of his Corvette convertible on Interstate 4 when trying to avoid contact with another vehicle making a lane change, destroying over 55 feet of steel security railing in the process.