Tennessee executed Harold Wayne Nichols by lethal injection Thursday in Nashville for the 1988 rape and murder of Karen Pulley, a 20-year-old student at Chattanooga State University.

Nichols, 64, had confessed to killing Pulley as well as raping several other women in the Chattanooga area. Although he expressed remorse at trial, he admitted he would have continued his violent behavior had he not been arrested. He was sentenced to death in 1990.

“To the people I've harmed, I'm sorry,” Nichols said in his final statement. Before Nichols died, a spiritual adviser spoke to him and recited the Lord’s Prayer. They both became emotional and Nichols nodded as the adviser talked, witnesses said.

Media witnesses reported that a sheet was pulled up to just above Nichols' waist and he was strapped to a gurney with a long tube running to an IV insertion site on the inside of his elbow. There was a spot of blood near the injection site. At one point he took a very heavy breath and his whole torso rose up. He then took a series of short, huffing breaths that witnesses said sounded like snorting or snoring. Nichols’ face turned red and he groaned. His breathing then appeared to slow, then stop, and his face became purple before he was pronounced dead, witnesses said.

Nichols’ attorneys unsuccessfully sought to have his sentence commuted to life in prison, citing the fact that he took responsibility for his crimes and pleaded guilty. His clemency petition stated “he would be the first person to be executed for a crime he pleaded guilty to since Tennessee re-enacted the death penalty in 1978.”

The U.S. Supreme Court declined to issue a stay of the execution on Thursday.

Jeff Monroe, Pulley’s brother-in-law, said the family “was destroyed by evil” the night she was killed.

“Taking a life is serious and we take no pleasure in it,” he said during a news conference following the execution. “However, the victims, and there were many, were carefully stalked and attacked. The crimes, and there were many, were deliberate, violent, and horrific.”

Pulley, who was 20 when she was killed, had just finished Bible school and was attending college in Chattanooga to become a paralegal, Jeff Monroe said.

Nichols has seen two previous execution dates come and go. The state earlier planned to execute him in August 2020, but Nichols was given a reprieve due to the COVID-19 pandemic. At that time, Nichols had selected to die in the electric chair — a choice allowed in Tennessee for inmates who were convicted of crimes before January 1999.

After the execution, Nichols' spiritual advisor, J.R. Davis, read a poem about forgiveness that Nichols wrote.