Daryl Wheatfall, then 25, was initially sentenced to death for the murders of James and L.B. Fitzgerald, 62 and 67, in southeast Houston.
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According to attorneys, Wheatfall and an accomplice, Mack Terrell, went into the couple's Sunnyside home shortly after the 62-year-old returned from work.
The 67-year-old was struggling to wield a shotgun and the walker she relied on when Terrell took it away from her and removed the ammunition, according to prosecutors.
Terrell searched the home for any money he could find after realizing the Fitzgeralds did not have $50.
The couple's son, James Fitzgerald Jr., and Wheatfall began a brief fight, which led to the 19-year-old being shot, according to arguments during the latest hearing.
Prosecutors added that Fitzgerald Jr. did not know that his parents were killed until he woke up at a hospital.
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In 2015, the Texas Court of Criminal Appeals threw out the death sentence based on the judge in the initial case giving flawed jury instructions.
The state's highest criminal court ruled back in 2015 that jurors who sent Wheatfall to death row in 1992 had instructions during his trial's punishment phase found to be unconstitutional.
His trial was held at a time when the Texas jury instructions covering mitigation issues in death penalty cases were evolving under U.S. Supreme Court decisions. The appeals court ordered his case be returned to the trial court for a new sentencing hearing.
More than eight years after the appellate ruling, the jury in his new sentencing heard his case from about 2 p.m. until 7 p.m. on Tuesday, prompting a sequester overnight.
The Harris County District Attorney's Office was adamant about having Wheatfall's death sentence stand, but Wheatfall's attorneys asked the jury to consider life imprisonment instead.
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Wheatfall's attorneys attempted to steer the weight of Terrell's role in the killing, but on Wednesday, after more than 10 hours of deliberation, jurors decided to send Wheatfall back to death row after hearing the closing arguments.
Attorneys argued that the now-57-year-old is a changed man, adding that he now relies on a cane to walk and had his prostate removed after a cancer diagnosis.
According to ABC13's news partners at the Houston Chronicle, Assistant District Attorney Sarah Seely argued Wheatfall's roles in other incidents, including an instance where he stabbed a Texas Department of Criminal Justice guard with a makeshift spear after his death row confinement.
Wheatfall maintained his innocence in the months before the latest trial. The Houston Chronicle reported that he told District Judge Kelli Johnson he mistakenly befriended someone who was "not a true friend."