Normally Sing Sing’s electric chair, the legendary Old Sparky, accommodated single or double executions. Triples were less frequent, quadruples a rarity and very seldom did five convicts die on the same day. December 9 1920 was one of those days. State Electrician John Hurlburt (in the post since 1914) was firmly established as perhaps the leading ‘electrocutioner’ in the country.

According to his standard deal, that night he would earn $350 for his services, $150 for the first prisoner and $50 per head thereafter. The State Electrician might have been a private contractor but, being paid out of the public purse, the State of New York liked to pay its servants as cheaply as possible.

That deal (agreed with the first State Electrician, Edwin Davis) remained in place until the reign of Dow Hover (the Empire State’s fifth and last). It was a lucrative enough position at the time and Hurlburt (though he came to detest the job and its effect on him) needed the money. With a chronically-ill wife and medical bills always on his doormat, he had little choice but to continue killing to order.

Hurlburt’s successor Robert Elliott earned as much as $46,000 between 1926 and 1939, performing executions in six different states. Elliott was so busy that he once carried out two triple executions in two different states on the same day. That night Hurlburt’s job was slightly easier. He only had to kill five men in cold blood in one place, one after another. It wasn’t the first time he’d done so.

The five in question were of little particular note, four members of the Milano gang and another whose death warrant happened to coincide with theirs. Not that that made Warden Lewis Lawes’ job any easier. Simultaneously America’s leading opponent and practitioner of capital punishment, Lawes hated executions with a passion. He always said he’d never actually seen one, closing his eyes just before signalling the executioner to do his job. That night he would close his eyes five times, five out of the 303 convicts who died at his command, if not to his liking.

As was standard the prisoner most likely to break down was brought in first. Milano Gang member Howard Usefof was also claiming innocence. He denied shooting subway ticket agent Otto Fialo to the end. Co-defendant Joseph Milano supported Usefof’s claim at first, issuing a written confession that had cut no ice with the authorities. Usefof died far calmer than expected, issuing only a brief final remark before taking his seat:

“You see an innocent man dying tonight. Thank you, Warden, you have been a kind man.”

Minutes later Usefof, innocent or guilty, was also dead. Hurlburt had already earned the lion’s share of his fee. One down, four to go.

Next was Joseph Milano himself. Milano’s confession might just have saved Usefof had Milano not retracted it. As he began his last mile, actually around twenty steps between his cell and the chair, he was serenaded on his way by fellow gang-member James Cassidy. As Milano left on his final walk Cassidy, himself due to die that night, sang him on his way with ‘Oh, What a Pal was Mary.’

Perhaps feeling remorse at having sealed Usefof’s fate (though probably little at having murdered Fialo) Milano went to his death denying Usefof’s guilt but not his own. His last words were simple ones:

“Usefof did not take part in this crime.”

His death was as simple as his final statement. With two of the five now gone, it was time for Charles McLaughlin to pay his debt, increasing Hurlburt’s fee in the process. When Lawes had made his final visit before the executions McLaughlin had been putting on a brave face. He’d even put his hand through the cell bars, offering it to Lawes accompanied by the words:

“Shake, put it there, shake.”

As seemingly calm and cheerful when the time came, McLaughlin maintained his buoyant attitude (or façade) right to the end:

“God bless you, boys, I got the old smile on my face.”

With that he turned sat down and was dead minutes later. Another $50 was added to Hurlburt’s fee for the night’s work. Now, having serenaded Milano to his end, it was time for James Cassidy to face his own. Cassidy, who at least one doctor admitted had the mind of a nine-year-old, had arrived at the Death House illiterate, but willing to learn. Hours before his death he had written the Remembrance on his cell wall, a breach of prison regulations. True to form Lawes overlooked it as he visited Cassidy for the last time, especially when Cassidy pointed to it, remarking:

“Isn’t it Hell, Warden, when you get so you can write words like that to have to be bumped off..?”

As he entered the death chamber Cassidy, a talkative man by nature, had a little more to say. Knowing Lawes’ hatred for executions Cassidy made a point of greeting him as he walked calmly through Sing Sing’s infamous ‘little green door.’:

“I know I’ve done wrong. I know I’m paying for it. Hello Warden, I see you back there, old-timer.”

As he sat down, still as chatty as ever, Cassidy had time for one last remark:

“Give her the gas, kid. I’m taking it with a smile.”

A silent wave of Lawes’ hand was followed by Hurlburt’s immediately jerking the switch and the conversational Cassidy was no more. Minutes later he was unstrapped, placed on a trolley and wheeled away. Four down, one to go and $300 to Hurlburt’s credit. Now only Howard Baker remained.

Baker was the only man that night who wasn’t part of the Milano Gang. Baker had been in a gang of his own beside his mother and her toy-boy lover. While robbing a clothing store the gang had been surprised by a night watchman. In turn Baker had surprised the night watchman with a fatal gunshot wound. As he left his cell Baker had bidden his fellow-condemned a simple farewell:

“Goodbye, boys.”

As he sat down Baker became a little more talkative in the few seconds left to him:

“If I’ve got to leave this good old Earth, I want to make a statement before I go. I’m feeling all right, but it’s over others I’m worrying.”

His remark was dignified, presumably showing a concern for those who’d cared for him. It also conformed to the convict tradition in the face of death; Never let them see your fear. Minutes later Baker was gone, wheeled into the adjoining morgue and autopsy room. Another $50 was owed to the State Electrician.

Hurlburt packed away his equipment and collected his unusually-large fee. Those remaining in the condemned cells could clearly hear prison doctor Amos Squire’s bone saw as he began the autopsies mandated by State law. Knowing full well those remaining could hear him at his grim task it was a sound Squire detested inflicting as much as the condemned hated to hear. The men’s few personal possessions were removed and their cells made ready for whoever would occupy them next.

No matter how many passed through the little green door, whether they walked, were dragged or had to be carried, in the 1920’s there was always somebody to take their place. Hundreds more would do so.

The careers of Warden Lewis Lawes, John Hurlburt and New York’s four other State Electricians covered more fully in my new book Murders, Mysteries and Misdemeanors in New York which, by a handy coincidence, was published in bookstores and online on November 25..