In 1989 Askew killed his pregnant 15-year old girlfriend and wounded a couple of her relatives.
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After doing his time in state prison for those crimes, he was released-only to murder another girlfriend and wound her sister, prosecutors have charged.
Now family members of Sylvia Brice, whom authorities say was Askew's latest victim, want to know how such a violent criminal could be on the streets only to con and kill again.
"It happened so fast," said Montra Tuffour, Brice's niece, who says she was stabbed six times during the attack in which her aunt died. Tuffour called 9-1-1 from her aunt's home near Chicago's Roseland neighborhood-as the knife attack was underway. Her screams can be heard on police tapes obtained by the ABC7 I-Team.
"So I'm still on the call-next thing you know he pulls out this big large kitchen knife and stabs me right here," Tuffour said. Photos of her wounds show horrific cuts in her abdomen that had to be stapled closed.
Brice, 52, had dated Askew for a short time according to family members who say she had no idea of his criminal past.
After a rocky breakup, the mother, grandmother and school teacher obtained a court order of protection to keep Askew away.
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About a month later, on New Year's Eve of 2016, Askew went to her home anyway in the 9300-block of South Wentworth Avenue according to police and court records.
Tuffour says she and her aunt tried to get Askew to leave, but that he went after them with a knife.
He is charged with murder and aggravated battery and has pleaded not guilty.
Family members say they want to know why Askew served only 20 years of a 40-year sentence, had numerous other criminal arrests when he got out, but was still out on the street to terrorize them?
An official from the Illinois Prisoner Review Board that oversees such decisions said violations and offenders are evaluated on "a case-by-case basis." The board's chief legal counsel Jason D. Sweat said that, "members of the Board who heard Mr. Askew's violation cases in 2013 found, under the totality of the circumstances and evidence available to them, that Mr. Askew had violated his release. The Board's findings resulted in additional incarceration in the Department of Corrections, as well as additional restrictions upon his return to the community. Ultimately, after the second violation, Mr. Askew remained confined until he reached the maximum of his possible sentence."
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He was released in 2014 and is charged with killing again in 2016. Sylvia Brice's loved ones have hired Chicago attorney Marty Dolan to look into their questions.
"We want to challenge what's is going on here," said Dolan. "There's got to be mechanisms in place in these situations-where you got an ex-murderer coming out, now he's on a domestic, he's in court and as soon as somebody realizes from records he's on parole --there has to be something that's done."
"The bottom line is, we want justice for Sylvia's death because it was senseless and it should not have happened," said the victim's sister Odessa Brice.
Askew's attorney, public defender Christopher Anderson, told the I-Team that he "is vigorously defending Mr. Askew's rights to a fair trial in this matter, and would like to remind (ABC7) viewers that he is presumed innocent of these charges."
Askew's next court appearance isn't until January, when DNA evidence test results are expected to be completed. If the case goes to trial, the state's key witness is expected to be surviving niece, Montra Tuffour, who told the I-Team, "Every day I ask God to, you know, help me make peace with it, help me make peace with the fact that she's gone and that you know I still have to continue on with my life."