William James “Flip” Williams Jr. was born on November 9, 1956, and raised in Youngstown, Ohio. From a young age, Williams became immersed in crime, particularly drug dealing and robbery. He developed a reputation in the city as a hardened career criminal and was said to be ruthless in both his drug business and street dealings.

By the early 1980s, Williams had already been tried for murder, though he was acquitted in 1981. He spent five years in a California prison for cocaine trafficking and bank robbery, strengthening his reputation as a dangerous and calculating figure. His nickname “Flip” became well known in Youngstown’s criminal world.

Williams was ambitious and protective of his territory. When he returned to Youngstown after his time away, he discovered that his former drug business had been taken over by new rivals.

The crime that sealed Williams’s fate took place over the course of September 1–2, 1991, in Youngstown, Ohio. His targets were three rival drug dealers including Alfonda R. Madison, William L. Dent, and Eric Howard who had taken over his former operations. A fourth victim, Theodore Wynn Jr., became collateral damage.

Williams orchestrated the murders with the help of three young accomplices: his 16-year-old girlfriend, Jessica Cherry, her brother, Dominic Cherry, and Dominic’s 17-year-old “cousin,” Broderick Boone.

The plan began with Jessica Cherry visiting Madison’s home under the guise of arranging a drug deal. Later that night, Williams and the group arrived. Armed with walkie-talkies, the young accomplices entered first, holding Madison at gunpoint. They signaled for Williams, who entered and handcuffed and gagged Madison with duct tape.

Soon after, Theodore Wynn Jr. knocked on the door looking for Madison and Howard. Jessica lied, telling him they were not home, but Williams realized Wynn could identify them. Wynn was lured inside, restrained, and gagged. Jessica was then sent to lure William Dent by phone. Dent arrived with Eric Howard, and both men were ambushed and forced into the bathroom.

Williams then personally strangled Madison and Wynn, before executing all four men with a gun belonging to Madison. Their deaths effectively eliminated his rivals in one night.

On September 24, 1991, Dominic Cherry turned himself in to police. His confession led to the arrests of Jessica Cherry and Broderick Boone. Williams himself was arrested soon after, but on October 15, 1991, he escaped custody. While a fugitive, he was indicted on four counts of aggravated murder, four counts of kidnapping, and one count of aggravated burglary.

Williams resurfaced dramatically on January 12, 1992, when he stormed the Mahoning County Juvenile Justice Center with two armed men. They tricked the receptionist to gain entry, then held her and a deputy sheriff hostage. Williams demanded access to Jessica, Dominic, and Broderick—his former accomplices—intending to kill them so they could not testify. After tense negotiations, he eventually surrendered. His indictment was expanded to include twelve counts of aggravated murder and additional charges of kidnapping and burglary.

The three juvenile accomplices all pleaded guilty to reduced charges of complicity in murder, kidnapping, and burglary. Williams, however, pleaded not guilty. In 1992, he was convicted on all counts and sentenced to death.

Williams’s trial attracted widespread media coverage due to the brutality of the killings and the youth of his accomplices. Despite appeals and attempts to delay execution, the Ohio Parole Board unanimously recommended against clemency. On October 24, 2005, Governor Bob Taft upheld the decision.

On October 25, 2005, at the Southern Ohio Correctional Facility in Lucasville, Williams was executed by lethal injection. He declined a final meal, requesting only a cup of coffee. In his final statement, he expressed love for his family but dismissed his case, saying:

“I’m not going to waste no time talking about my lifestyle, my case, my punishment. Mom, you’ve been there for me from the beginning. I love you. To my nieces, nephew and uncle I love you very much. Y’all stick together. Don’t worry about me. I’m OK. This all ain’t nothing. That’s it.”

Williams was pronounced dead at 10:20 a.m. EDT, aged 48.