Condemned To Death: 5 of America’s Longest Serving Death Row Inmates

Condemned To Death: 5 of America’s Longest Serving Death Row Inmates

Patrick Lynch - March 26, 2017

The existence of the death penalty in 31 states (and the federal government) continues to cause controversy as human rights activists try to claim it is a barbaric method of punishment. On the other side of the coin, proponents of the death penalty say it is the correct sentence for anyone found guilty of committing murder. There are over 3,000 Death Row inmates in the U.S. 1,447 people have been executed in the country since 1976.

Approximately 65% of Americans agree with the death penalty, and the vast majority of executions are carried out by lethal injection. The main issue with Death Row is the length of time inmates spend there before being put to death. There is an average of almost 16 years between sentencing and execution on Death Row, and an increasing number of inmates are spending over 25 years waiting to die. The appeals process is a long and arduous one, and most prisoners use it as a means of gaining a stay of execution. In this article, I will look at 5 of the longest-serving Death Row inmates in U.S. history.

Condemned To Death: 5 of America’s Longest Serving Death Row Inmates
Raymond Riles. Murdermedia

1 – Raymond Riles (41 Years)

Riles has spent over 41 years on Death Row; the longest anyone has spent waiting to die in Texas, and one of the longest-serving Death Row inmates of all time. Riles was convicted of the murder of John Henry in 1974 during a robbery and sentenced to death the following year. Mental illness is what has prevented Riles’ execution to date.

On the fateful day in 1974, Riles accompanied Herbert Washington to John Henry Motors in Houston, Texas, where the latter previously bought a used car. Washington was angry because the vehicle had problems, so the duo confronted John Henry, the owner of the company, and demanded a refund. Henry said he wouldn’t issue a refund, but did agree to repair the vehicle. Riles ended up shooting Henry him from behind. Henry didn’t die immediately, and Riles stood over him and demanded money.

The dying man complied and Riles, along with Washington, traveled to Herby’s Foods and spoke to a manager about job openings. The manager refused to provide the men with job applications, so they robbed him and his wife and stole $1,800. The police saw the pair in Washington’s car and chased it at speeds of up to 100 mph. Eventually, Washington crashed his car, but instead of surrendering, the two men opened fire on the police and fled, only to be arrested soon after.

Riles’ unstable mental state was on full display during his trial when he continually interrupted proceedings to the point where he was eventually confined to a cell. During an interview with a psychiatrist, Riles acted like a dog; he attempted to bite her and started howling and barking. Washington said that he once witnessed Riles tying his wife to a railroad track as a train approached; he screamed ‘Repent, Jezebel’ at the terrified woman.

Although Washington received a death sentence, it was later overturned, but he did get a 50-year jail term for trying to murder a police officer in a different case. Riles also received the death penalty, but a retrial was necessary in 1978 because prosecutors used evidence from the Herby’s robbery during the murder trial. Nonetheless, Riles was again convicted and sentenced to death. He received the first of several stays of execution in 1980.

In 1985, Riles, along with nine other Death Row inmates in Texas, signed a petition to forego appeals and accept execution. However, as Riles has a mental illness, it is highly unlikely that he will ever be executed. There is little question that Riles is mentally unstable. He blamed God for his suicide attempt in 1985 where he set himself on fire in his cell.

He has shown the bizarre workings of his mind in several interviews. For example, he claims ‘they’ are trying to silence him because he knows about the secret satanic societies of the TDC shadow government e-system. One wonders if people such as Riles and the next man on this list should be confined to mental institutions instead of wasting time on Death Row when they most likely won’t be executed.

Condemned To Death: 5 of America’s Longest Serving Death Row Inmates

2 – Gary Alvord (39 Years)

In the end, it seemed as if Gary Alvord was ‘too crazy’ to be executed. He was sentenced to death for a triple murder on April 9, 1974, but died from a brain tumor on May 19, 2013. Alvord was convicted of the cold-blooded killings of Georgia Tully, her daughter Ann Hermann, and her granddaughter Lynn Herrmann which occurred on June 18, 1973. There was no doubt about his guilt and the vicious nature of the murders. The fact that he also raped Lynn Herrmann meant few people complained when Alvord was sentenced to death in Florida the following year.

Alvord was born in Michigan in 1947 and doctors suggested he suffered from antisocial personality disorder and paranoid schizophrenia from a young age. He was jailed for raping a 10-year-old girl in 1967 but was released after three years because a jury overturned the verdict and declared he was not guilty because of insanity. Alvord spent the next three years in a mental institution but escaped and managed to live a relatively normal existence; he even had a girlfriend.

It was always likely that Alvord would revert to his criminal ways, and he did so in the most violent manner within a few months of his move to Tampa. One day, the owner of the Guys and Dolls Billiard Hall, Ann Herrmann, got into an argument over the cost of a pool game with someone Alvord knew. Apparently, Alvord said: “Usually when someone rips off my friends, I kill them.” Unfortunately, this was no idle boast, because Alvord broke into the Herrmann house and strangled three generations of the family. At that time, he used the alias ‘Paul Brock’ and confessed the murders to his girlfriend.

Alvord was among half a dozen inmates considered in the late 1970s when prominent people in the state of Florida began looking to resume executions, but his mental state prevented it. In what is a terrible paradox, Alvord was on Death Row in the first place because he was most likely insane, yet this mental condition ensured he could never be executed. He was sent to a state facility in 1984 to receive treatment yet doctors refused to comply; they didn’t want to restore his mental faculties just to ensure he died.

Alvord was returned to Death Row in 1987 and remained there until his death in 2013. His lawyer, Bill Shepherd, complained about a ‘sick’ system that spent a fortune keeping a man who couldn’t be killed on Death Row. During the 39 years Alvord waited to die, 75 other prisoners were executed in Florida, with most of them spending less than half the time that he did on Death Row. Death warrants were signed for him in 1981 and 1984, but he was always deemed mentally unfit. In the end, Alvord died from a brain tumor; his health was poor in his later years as he also suffered from lung cancer.

Condemned To Death: 5 of America’s Longest Serving Death Row Inmates
Brandon Astor Jones. Chattanooga Times Free Press

3 – Brandon Astor Jones (36 Years 4 Months)

On February 3, 2016, Georgia’s oldest Death Row inmate, 72-year-old Brandon Astor Jones, was executed by lethal injection. He spent over 36 years on Death Row after being sentenced to death for murdering Roger Tackett during the robbery of a convenience store in 1979. Jones was the second man to die for the crime; his co-criminal, Van Roosevelt Solomon, was electrocuted in 1985.

It appears as if the two men attempted to rob the convenience store and perhaps Tackett tried to stop them. Both Jones and Solomon had guns, and both fired their weapons, although each man claimed the other fired the fatal bullet. A police officer heard four gunshots in total and arrested both men in the store. He found the seriously wounded Tackett in a locked storeroom, and he later died from his injuries.

While Solomon was executed within six years of the murder, Jones spent decades fighting against his sentence. A federal court ordered a re-sentence in 1989 after it ruled that a Bible was brought into the deliberation room. The court decided that the presence of the holy text would persuade jurors to base their decision on Scripture rather than on the law. However, another jury sentenced Jones to death in 1997, but he continued to appeal. According to Jones, his lawyers did not introduce evidence of his history of childhood sexual abuse and mental illness.

Jones’ case brought to light a disturbing trend in the state of Georgia. In 2005, the state opened the Office of the Georgia Capital Defender. The goal was to find a solution to the age-old problem of defendants on trial for capital crimes with a low standard of representation. When Jones was on trial in the late 1970s, any member of the Georgia Bar could represent someone in a death penalty case. According to Stephen Bright of the Southern Center for Human Rights in Atlanta, the result was that people were sentenced to die because they had a bad lawyer instead of being sentenced for committing a terrible crime.

The case also brought up the issue of racial bias. Both Jones and Solomon were African American, and Georgia has a history of black men and women receiving woefully inadequate defense while also receiving disproportionally harsh sentences. In 1974, five years before Jones committed his crime, a man named Wilburn Wiley Dobbs received a death sentence for murder during a robbery. He court-appointed attorney didn’t bother trying to mount a defense and called Dobbs ‘boy’ throughout the trial. The attorney later admitted that he believed black people were inferior to whites.

There are numerous other instances of probable racial bias in capital crime trials, but in 1987, the Supreme Court ruled in the McCleskey case that racial bias in handing down death sentences wasn’t unconstitutional unless intent was proven. Critics called it ‘New Jim Crow’ and suggested that the ruling immunized the justice system from instances of racial bias.

Jones made a final attempt to have his sentence commuted to life imprisonment in January 2016, but failed and was executed by lethal injection on February 3, 2016. It was a messy execution and took almost an hour as the executioners struggled to find an appropriate vein on Jones’ left and right arms. Eventually, a doctor injected it into his groin.

Condemned To Death: 5 of America’s Longest Serving Death Row Inmates
Bittaker (left) and Norris (right). Sick of your Crap

4 – Lawrence Bittaker (36 Years)

While everyone on this list was convicted of a capital crime, Bittaker could be considered the most evil man in this article. Along with his accomplice Roy Norris, Bittaker raped, tortured, and murdered five teenage girls over a period of several months in 1979. Even allowing for the slow-turning wheels of justice, it is remarkable that Bittaker has yet to be executed. Norris received a life sentence in return for testifying against his partner in crime.

The vile nature of their deeds is such that experienced FBI agent John Douglas said Bittaker was the single most disturbing individual he has ever performed a criminal profile on. Steven Kay, a prosecutor in California, said Bittaker was the worst criminal he has ever encountered, with his partner Norris a close second. In his opinion, Bittaker deserves the death penalty more than anyone in the state of California, yet he is still alive.

Both Bittaker and Norris were career criminals; Bittaker served time for attempted murder while Norris was convicted of assault with a deadly weapon and within months of his release, he raped a young woman. They met in prison in San Luis Obispo and soon came up with a plan to murder a teenage girl of every year from the ages of 13 to 19. They put their plan into action soon after their respective releases. For a four month period in 1979, they picked up 20 female hitchhikers. They did not assault any of these women; the purpose was to conduct ‘trial’ runs to see how easily they could lure women into their van.

Satisfied with their reconnaissance, they murdered their first victim on June 24, 1979. She was the first of five victims with the final girl murdered on October 31, 1979. They became known as the ‘Tool Box Killers’ because the items they used to torture and kill victims were found in a household toolbox. Although Bittaker apparently has one of the highest IQs of any Death Row inmate in the United States, his partner seemingly does not because Norris bragged about the crimes to an acquaintance named Jimmy Dalton. Dalton reported the information to the police and a young woman named Robin Robeck identified Bittaker and Norris as the two men who raped her on September 30. For some reason, they allowed her to escape in the midst of their murderous spree.

Police arrested both men and found evidence of their crimes. They were found guilty, and Bittaker received the death sentence on March 24, 1981. Norris testified against Bittaker with the guarantee that he would not be executed. He was eligible for parole in 2009, and while it was turned down, he could be released in 2019. To date, Bittaker has filed approximately 40 frivolous lawsuits while in prison; complaining about receiving crushed sandwiches and broken cookies and suggesting they are examples of ‘cruel and unusual punishment. He has also claimed he is afraid of death, and it appears as if he will die in his San Quentin cell as there is no plan to execute him anytime soon.

Condemned To Death: 5 of America’s Longest Serving Death Row Inmates
Jack Alderman. MYAJG

5 – Jack Alderman (33 Years)

At the time of his execution in Jackson, Georgia on September 16, 2008, Alderman had the distinction of being the longest-serving Death Row inmate to be executed (later surpassed by Jones). This is one of the reasons why he makes the list when others such as Thomas Eugene Greech, Michael Morales, and Albert Greenwood Brown have spent longer on Death Row. There are suggestions that Alderman might have been the victim of a gross miscarriage of justice as the circumstances surrounding the murder of his wife Barbara Jean on September 21, 1974, were not completely clear. Her body was found in her car in Effingham County, and the county police detained Alderman the following day and kept him in prison for 10 days.

Meanwhile, a man named John Brown was also questioned and he initially confessed to beating Barbara Jean to death with a wrench. However, Brown changed his story and claimed he killed the woman with Alderman who allegedly paid him for his help. Later on, Brown admitted that he accepted benefits to testify against Alderman.

The case against Alderman was weak; the prosecution claimed he tried to defraud a sum of $20,000 from his wife’s life insurance. Other than this motive, the only real evidence against Alderman was Brown’s testimony as the prosecution had no forensic proof. He refused plea bargains that would have saved his life because he protested his innocence and would not confess to a crime he apparently didn’t commit.

In November 1974, there was supposed to a preliminary hearing which was a joint indictment of Alderman and Brown, but the State did not present Alderman’s attorney with crucial documents until two working days before the hearing. As a result, the lawyer (who was 78-years-old) did not speak on his client’s behalf, which meant the joint indictment became separated into two trials with Alderman in court first. Despite relying on the testimony of the alcoholic, drug addicted Brown, the prosecution succeeded in its task and Alderman was found guilty and sentenced to death on June 14, 1975.

Brown was also found guilty and sentenced to death in November 1975, but his sentence was commuted to life imprisonment in 1978. Alderman was supposed to be executed on July 6, 1980, but a Federal Judge ordered a retrial while the State of Georgia appealed. In 1985, Alderman was offered life imprisonment in exchange for a guilty plea, but again, he refused and was found guilty and sentenced to death on April 1.

Over the next quarter of a century, he had numerous appeals turned down and a number of organizations in Europe appealed to the United Kingdom’s Foreign Secretary to ensure Alderman received a stay of execution. These attempts failed, and the unfortunate man received one more false piece of hope in 2007 when his original execution date was canceled as the Supreme Court debated on the constitutionality of death by lethal injection. Finally, Alderman died on September 16, 2008, and to this day, a large number of people familiar with the case believe an innocent man died.