In a court hearing early Monday, a Harris County judge signed a death warrant for 66-year-old Danny Bible.
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"Some criminals' actions are so heinous, they earn the label 'worst of the worst,'" Harris County District Attorney Kim Ogg said. "The jury who listened to the facts and saw the evidence of the crimes Danny Bible committed clearly reached that conclusion by sentencing him to death."
In May 1979 in Houston, Bible brutally raped and stabbed Inez Deaton to death with an ice pick. Deaton, 20, was married and the mother of a 2-year-old girl. She was also best friend's with Bible's cousin.
For nearly two decades, Deaton's murder went unsolved. In the meantime, Bible fled Texas, but later returned and murdered three more people.
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In 1983, Bible raped and murdered Pam Hudgins, Tracy Powers and Powers 4-month-old son, Justin.
Bible was eventually caught in 1984 and pleaded guilty to murdering Hudgins. He was sentenced to 25 years in prison.
He was released on parole in 1992, after just 8 years.
While still under supervision Bible raped five young family members.
The quadruple killer then fled to Louisiana in 1998, where he brutally attacked and raped another woman.
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VIDEO:Rare look inside San Quentin Prison, home of death row
During the interrogation for that attack, Bible confessed to Deaton's murder after nearly two decades.
A Harris County jury convicted Bible of capital murder in 2003 and sentenced him to death.
Over the course of many years, Bible challenged Texas' death penalty, raising claims about alleged bias during his case.
On Monday, Bible appeared in the 351st State District Court in Harris County for a hearing, and a judge signed off on the execution order and issued a death warrant.