Sending convicts to 'Old Sparky' was a solemn duty in one of America’s oldest correctional facilities. Situated in New York State, Sing Sing carried a dark legacy, with the executioner earning a hefty sum to pull the fatal switch.
In the early 20th century, newspapers around the globe covered stories about criminals condemned to die in the electric chair. Public debates raged over whether the electric chair was a cruel or humane method of execution, with some questioning the culpability of the condemned.
Certain journalists used dark humor, while others attempted to report the cases impartially. Numerous articles sought to humanize those who met their end in the chair, while a few cruelly detailed their final moments.
10. The New Chair

In 1892, newspapers were abuzz with reports that Sing Sing had introduced a new electric chair. Charles McElvaine, a convicted murderer, became the first man to sit in it, and his final hours were documented for all to read.
At midnight, the death warrant was read to Charles. The warden, in a bizarre show of kindness, suggested that he sleep, as though rest was necessary before sitting in the electric chair. The following morning, a priest arrived, and the prisoner ate a simple breakfast. Carrying a cross, Charles walked to the chair, where he was strapped in, and then:
The first shock, at 11:15, passed through his hands and head for forty-five seconds, followed by a second shock to the head and the right calf. Moments after the first shock ended, foam emerged from his mouth, accompanied by a choking gurgle. The current was quickly reapplied for another 45 seconds, after which the doctors examined him and declared him dead.
9. Smile

In 1921, five men were condemned to die in Sing Sing’s electric chair. Strangely, it was reported that some of them were resolute in facing death with a smile. Two were convicted murderers, while the other three had assisted in one of the killings.
On the day of the executions, the first man approached the chair and declared, “You will now witness the death of an innocent man. I will die with a smile on my face. Can you see it?”
After he was declared dead, the second man, a mere 20 years old, was brought forward. Trembling with fear, he needed assistance to sit in the chair. He had no words to say.
The third man, branded as an 'imbecile,' entered the room and boldly proclaimed that he would face death with a smile. The fourth prisoner walked in and greeted everyone with a 'hello,' and as the final electrode was applied, he simply said goodbye.
The last prisoner sat quietly in his cell, singing 'Oh, What a Girl Was Mary' while the others were executed, until his turn arrived. When he entered the room, he admitted, 'I know I’ve done wrong and I deserve to die.'
Once strapped into the chair, he shouted, 'Let ‘er go!' He was the only one who appeared to die with what resembled a smile. Sadly, this man was also classified as a 'mental defective' and may not have fully understood the gravity of his fate.
8. Not Just For Men

Sing Sing didn’t only execute men. Women faced the same fate. In 1935, for example, it was reported that Mrs. Eva Coo met her end in the electric chair.
Mrs. Coo was the owner of a roadside amusement park. Whether driven by greed or desperation, she decided to kill one of her employees for the insurance money. She first knocked him unconscious by striking him over the head with a blunt object.
While he lay on the road, she drove her car over him several times, hoping to make the incident appear accidental. However, running over a victim multiple times doesn’t typically look like a simple accident.
Mrs. Coo was arrested, convicted, and sent to Sing Sing to await her execution. In June 1935, she was placed in the electric chair. Shortly after her death, a gangster took her place.
7. Anything To Avoid The Hot Squat

Louis Boy had spent 18 years in Sing Sing for murder and was awaiting his turn in the electric chair when he was offered the chance to participate in a medical experiment. The purpose was to help a young girl suffering from leukemia. Boy consented to have '18 quarts of blood in his body [to] pass through the body of the stricken child in a vein to vein exchange.'
Sadly, the young girl died a few days after the experiment. However, Louis Boy was granted his freedom by the governor in 1949 for his participation in the experiment.
6. A Song And Dance

In 1925, reports surfaced that US prisoners displayed unusual behavior on execution days. Unlike in England, where prisoners were confined to their cells, staying there until 'the whole terrible thing is over,' Sing Sing offered a different experience.
At Sing Sing, inmates were permitted to dance and sing during executions. At times, they even performed highly comedic plays. Though it may seem unsettling to allow the prisoners such freedom, there was a rationale behind it:
Because the law mandates executions to take place, they must. If the execution were canceled that night, many other prisoners in Sing Sing would be consumed by thoughts of the executions. With the entertainment ongoing, it gave them something else to focus on, which could be a blessing. It’s known that execution night brings extreme depression among the inmates. The realization of the events in the death house drives some to a frantic state. Therefore, if 'Sue, Dear' can help ease their mental anguish, it will have done a great service.
5. A Mother’s Last Goodbye

In 1934, Anna Antonio offered her three-year-old son an apple, marking her final gift to him. She was granted a few precious hours to play with him before giving him a farewell kiss.
Anna Antonio’s head was shaved as she was escorted to the electric chair. While whispering her prayers, she was strapped into the chair, and the helmet was placed over her head. Within moments, she was pronounced dead.
Some witnesses were so disturbed by the scene that they fainted, and the priest visibly struggled, crossing himself in dismay. She was the fourth woman to face execution in Sing Sing's electric chair, but she would not be the last.
She had been sentenced to death for the murder of her husband. The two men she had hired to carry out the crime were executed right after her.
4. Too Late To Learn Patience

Giovanni Ferraro, convicted of murder, was sentenced to die in the electric chair in 1919. Hoping for a reprieve, he believed the governor would commute his sentence to life after learning that another murderer had received such a commutation.
When Ferraro thought his plea for mercy had been denied, he went wild with rage. He attacked three guards with a knife, severely wounding two of them, and attempted to flee.
He was quickly subdued, and news of his violent outburst was sent to the governor. Despite the timing of the review, the governor ultimately rejected Ferraro’s plea after hearing of his actions.
It was revealed after Ferraro’s execution that the governor had almost certainly planned to spare his life before hearing of his violent outburst.
3. A Horrific Death

Initially, the electric chair was introduced as a more humane alternative for carrying out executions. Thomas Edison himself worked on refining the electrical charge for the chair, aiming for an approach that would be both more efficient and less painful than hanging. However, early executions using the chair were far from the humane solution it was intended to be, with results that were often gruesome.
In 1926, the chaplain at Sing Sing recounted a harrowing account of an execution performed on an experimental electric chair from the late 1800s. The condemned man was strapped into the chair, a polished brass cap placed on his head, and no gag was used. When the switch was thrown, the man screamed out in agony. His convulsions were so violent that one of the leather straps holding his arms snapped.
Still alive, the prisoner was given a second shock. Once again, he screamed and convulsed. The priest, witnessing the suffering, urgently pleaded with the others to end the man's misery.
The governor, who had come to observe the execution, quickly stood up, seized the switch, and sent a powerful, unbroken flow of electricity through the prisoner. It took eight minutes for the prisoner to finally die in the chair.
2. Paid Well

Despite the inherent risks of the executioner's role at Sing Sing, 85 individuals had already applied for the position just two days after it was announced that John Hulbert had resigned. Men were eager to secure the job, competing fiercely for the opportunity.
The reasons behind the interest in this job were likely diverse, but the most appealing factor was the potential earnings. The executioner's role offered a base salary, along with additional bonus pay on execution days. In some cases, the total could exceed $400 per day, a significant sum for 1926.
It was rumored that the warden was eager to fill the role quickly. Although he opposed capital punishment, he realized that without an executioner, he would have to perform the executions himself.
1. Not An Easy Job

John W. Hulbert served as the executioner at Sing Sing from 1913 until 1926. Throughout his tenure, he received multiple threats on his life. A man of solitude, he avoided sleeping cars, fearing for his safety.
Before one execution, Hulbert's food was poisoned, almost preventing him from performing his duties. On another occasion, he traveled to Omaha to demonstrate the electric chair, where he was confronted by an angry mob and narrowly escaped lynching. Eventually, he left his post, stating, 'I got tired of killing people.' Hulbert oversaw 140 executions at Sing Sing.
In 1929, Hulbert was found dead in his home with gunshot wounds to his abdomen and head. His death was officially ruled a suicide.