Billups had an extensive history of violence off the football field. 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. She later dropped the criminal charges, but filed a civil lawsuit against Billups. In Billups' civil trial, Fair testified that he threatened to hire someone to cut Fair's face with a razor blade and "finish the job" if she did not drop the criminal charges. Fair also testified that she required six operations on her face from the assault, including a
bone grafting procedure in which her nose was reconstructed with bone pulled from her skull and ribcage. Billups ultimately paid Fair $30,000 in an
out-of-court settlement. 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. He pleaded not guilty. He was later found guilty of all charges by a jury and sentenced to serve 30 days in the Hamilton County jail. In the other call, Billups said: "Now, I'm telling you right now as God as my witness, I swear on my mother's life, if you ever speak to a guy, speak -- just say 'Hi' to a guy from Kentucky, I promise you (Billups' associates will) go see your brother and he'll never play basketball again." Billups flew up to Kentucky from Florida to meet Jenny, but instead was met by FBI agents and arrested. Numerous people testified about Billups' violent nature, including Jenny Chapman and Tracy Fair, and stated that they were fearful for their safety in Billups' presence. In October 1993, Billups pleaded
no contest in
Seminole County, Florida to a charge of criminal conspiracy. Billups was arrested in December 1992 and initially charged with criminal conspiracy as well as aggravated sexual battery and extortion, stemming from an incident where Billups, in collusion with a friend named Gregory Calloway, was accused of drugging and sexually assaulting a woman at Billups' residence in
Longwood while Calloway recorded the assault on videotape. According to the victim, Billups, who had been a neighborhood friend, invited her over to his home to join he and Calloway for lunch. An unspecified drug was then slipped into the victim's drink which caused her to pass out. The victim claimed that Billups then threatened to send copies of the videotape to her husband, other family members, and friends listed on her Christmas card list if she failed to meet Billups' demand of paying him and Calloway $20,000 each. Billups and Calloway were subsequently arrested in Seminole County on December 16 after warrants for their arrests were issued, and they were each released on $50,000 bond the following day. This case prompted multiple women to come forward and accuse Billups of sexually assaulting them in similar fashions, but no additional charges were filed. 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. Billups died just five days after his federal incarceration ended. == Personal life and death ==