Bucklew, who killed his ex-girlfriend's new boyfriend in 1996, claims an execution would violate his constitutional guarantee against cruel and unusual punishment. Photo / AP
WARNING: Graphic content
He shot and killed his ex-girlfriend's new partner before raping her and beating her mother with a hammer.
Two decades on, death row inmate Russell Bucklew is set to be executed in Missouri tomorrow, and it is likely to be particularly gory thanks to a rare condition from which he suffers.
His lawyer has warned there is a "very substantial risk" his lethal injection could lead to a "gruesome" and "excruciating" death as the murderer chokes and gags on his own blood.
Bucklew has cavernous haemangioma, a serious illness that leads to weakened and malformed blood vessels as well as blood-filled tumours in the nose and throat.
The 49-year-old was granted a stay of execution in May 2014, when the US Supreme Court halted proceedings amid concerns about Bucklew's medical condition — which his lawyer says has now worsened.
But a panel of the 8th US Circuit Court of Appeals has refused to stop the execution. An appeal and stay request are pending before the Supreme Court.
The appeal outlines the sickening scenario the prisoner's supporters believe could happen if he is executed tomorrow.
"Those highly sensitive tumours easily rupture and bleed," the appeal said. "As he struggles to breathe through the execution procedure, Bucklew's throat tumour will likely rupture.
"Bucklew's execution will very likely be gruesome and painful far beyond the pain inherent in the process of an ordinary lethal injection execution."
The court document claimed it would violate Bucklew's constitutional guarantee against cruel and unusual punishment.
His lawyer Cheryl Pilate asked for clemency from Republican Governor Eric Greitens. The appeals also have suggested if the execution is carried out, the state should use lethal gas instead of an injection of pentobarbital. Missouri law lists gas as an option, but the state no longer has a gas chamber and has not used the method since 1965.
None of the 20 inmates executed since Missouri began using pentobarbital in 2013 has shown clear signs of pain or suffering. The last execution in the state was in January last year.
Missouri Attorney-General Josh Hawley downplayed Bucklew's medical condition and cited continuing efforts over several years to put off the execution.
According to court documents, Bucklew was angry at his girlfriend for leaving him and moving in with Michael Sanders. He tracked her down at Sanders' home in March 1996 and killed his love rival in front of his ex, her two daughters and Sanders' two sons. He then attacked his former partner, drove her to a secluded area and raped her.
After a state trooper spotted Bucklew's car, Bucklew shot at the trooper but missed, court records say. He later escaped from jail, hid in the home of the ex-girlfriend's mother and beat her with a hammer.
"Hours of torture": Death row inmates escape execution
Death is not guaranteed for death row prisoners as legal teams and activists work hard to help them avoid the ultimate punishment.
Two weeks ago, an Alabama death row inmate sued after a "botched and bloody" execution attempt went wrong, leaving him under "physical and mental duress", according to his lawyer.
Doyle Lee Hamm — who was sentenced to death in 1987 for committing murder during a robbery — said he endured "hours of physical and psychological torture", with medics "forcing needles into his lower extremities" and a vein near his groin, "causing severe bleeding and pain".
The 61-year-old's execution by lethal injection was called off on February 22 after staff failed for 2.5 hours to find veins in his groin, feet and legs, CNN reported.
His defence team said the agonising procedure was cruel and unusual punishment and a "constitutionally prohibited cruel, unnecessarily painful, slow, and lingering process to death". The lawyers claim attempting another execution would be double jeopardy, violating the Fifth Amendment, which states that no person shall "be subject for the same offence to be twice put in jeopardy of life or limb".
Thomas Whitaker, whose execution in Texas was scheduled for the same day, was spared minutes before his scheduled death for arranging the murder of his mother and brother in 2003.
Whitaker's father Kent "passionately" opposed the execution of his son, claiming "he would be victimised again if the state put to death his last remaining immediate family member", according to Texas Governor Greg Abbott.
One man was put to death on that day, however. Eric Branch screamed "Murderers! Murderers!" as he was executed in Florida for the rape and brutal murder of a college student on campus in 1993.
The 47-year-old told correctional officers "you're good people, and this is not what you should be doing", saying state Governor Rick Scott and the Attorney-General Pam Bondi should administer the injection themselves.
Branch lodged numerous appeals, claiming the decades he spent on death row amounted to "cruel and unusual" punishment.
In response to one appeal, a Florida Supreme Court justice wrote that his victim, Susan Morri,s "had been beaten, stomped, sexually assaulted and strangled. She bore numerous bruises and lacerations, both eyes were swollen shut."