Clarence Ray Allen, convicted of ordering a hit in 1980 that resulted in the deaths of the target and two bystanders, was executed just after his 76th birthday, making him the second-oldest man in U.S. history to be executed. He had been in prison for ordering the murder of his son's girlfriend when he ordered the hit that resulted in the death penalty conviction. However, appeals caused him to remain on death row for 23 years. 
His lawyers had attempted to make the case that it would be cruel and unusual to execute the man, attempting to save his life under the Eighth Amendment to the United States Constitution. However, the courts rejected the appeal, and the Supreme Court refused to hear the case, upholding the death penalty conviction.
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Clarence Ray Allen is executed