Another formerly-famous crook, nowadays largely forgotten. Oreste Scillitano, AKA ‘Oresto Schillitoni’, ‘Harry Shields’ and several other aliases occupies a rare if not singular place in the annals of crime. There have been many triple murderers, many cop killers and more gangsters in New York than you could shake a billyclub at, but you can count on one hand the number who, having been condemned to death and shipped to Sing Sing Prison’s infamous ‘Death House’ managed a successful (though very brief) escape therefrom.

Oreste Scillitano, triple murderer and Death Houseescapee

Oreste Scillitano, triple murderer and Death Houseescapee

Death Rows across America have one thing in common. They’re populated by violent offenders who feel that, from their sentencing, that they have nothing to lose. Many don’t take advantage of that to cause trouble, but those who do are inclined either to cause as much trouble and violence as possible or to attempt escape. If they become perpetual trouble-makers then the worst that can happen is they end up in permanent solitary confinement. It’s not as though they’ll lose their time off for good behaviour and the threat of another piece of paper added to their conduct sheet is hardly a deterrent when they’re marked for death anyway. Their mantra is very simple and, for other inmates and prison staff, potentially very dangerous:

“What are you going to do about it? Kill me?”

The escape-minded have a different mantra, though no less iron-clad. For them it’s more a matter of playing the percentages, of taking the very slim chance of a successful break from Death Row (which has been managed more often than you might think) against taking your chances of your lawyer getting not only a removal of your death sentence but also getting either a pardon or a reversal of your conviction (in which case the authorities will be free to opt for a retrial anyway). Between a slim chance and no chance at all, it’s not hard to understand why Scillitano (convicted for murdering two cops in addition to another gangster) decided that his chance of escape (paper-thin though it was) far exceeded the likelihood of not having a seat in Old Sparky.

Born in Foggia, Italy on October 22, 1890 Scillitano was one of the thousands whose families brought them to America in search of a new and hopefully better life. Whether America was as enthusiastic about the life he chose (and the deaths he caused) is entirely more questionable. From a young age he was in trouble, serving a couple of juvenile sentences before resorting to full-time crime, starting off with theft and grand larceny for which he served a stretch in Sing Sing. His homecoming to the big house up the river wouldn’t be long in coming.

A confrontation with small-time hood John ‘Kid Morgan’ Rizzo on May 4, 1913 saw Scillitano (whose short fuse and violent nature were never far from the surface) murder Rizzo with a pistol. Rookie cop William Heaney heard the shots and came running. It wasn’t long before he too lay dying on the sidewalk. A Patrolman Teare also came running and soon joined Rizzo and Heaney slumped, fatally wounded, to the ground. Scillitano’s days as nothing ore than a low-level New York street thug were over.

The dragnet was nationwide. Police departments all over the country were only too happy to aid their New York brethren in catching a killer who had slain one of their own. The NYPD also put pressure of their own on Scillitano by arresting his father in connection with the murders, figuring that Scillitano (known to the underworld and NYPD alike as possessing some small sense of integrity) might feel an obligation to turn himself in in return for his blameless father’s release.

The ploy worked. On condition that the NYPD release and exonerate his father and brother (also arrested in connection with the slayings) and treat his family with respect, Scillitano sent word via the underworld grapevine that he would surrender and could be picked up on a street corner at Morningside Park at 9am on June 14. The NYPD kept their word and so did Scillitano. He was now under arrest pending trial for 3 counts of capital murder (New York had a mandatory death penalty for murder at the time) including the murders of 2 police officers. Barring some major miracle Scillitano’s goose was cooked. If the NYPD, District Attorney Charles Whitman and executioner John Hurlburt had their way, Scillitano would find himself done to a crisp as well.

Judge and jury concurred with that suggestion. On March 3, 1914 Scillitano was convicted on 3 counts of first-degree murder with no recommendation for mercy. Three days later Scillitano was on a train from New York to the upstate town of Ossining escorted by two heavily-armed detectives. Whoever was manning the ticket booth that day knew full well what it meant when detectives stood at the counter and made the standard request:

“3 tickets for Ossining. Two returns, one single.”

New York justice moved a great deal faster in the 1910’s than it does today. Scillitano was convicted and condemned on March 3. He was shipped to Sing Sing on March 6. His one automatic appeal was denied on May 9, 1916. Scillitano, a mixture of a violent rebel and a calculating plotter, had plans of his own to stay Hurlburt’s hand and they didn’t involve anything as lawful as fighting his case. Starting by constantly feigning insanity (which failed as the prison doctor Amos Squire was very wise to it through long experience) he somehow secured a pistol and a box of ammunition.

Going insane in the Sing Sing Death House was not by any means unusual. The building’s original layout had the execution chamber separated from the cells by only a single door, the infamous ‘Green Door.’ Inmates in the cells clearly heard everything during an execution. They heard the current running through the wires. They heard the prisoner’s last words if they had any. They heard the sound of the switch being thrown. Worst of all, New York law required an autopsy immediately after an execution. The inmates in the cells waiting their turn clearly heard the sound of the bone saw as the prison doctor removed the top of the deceased inmate’s skull to examine their brain. All in all, it wasn’t hard to be driven insane and many Death House inmates were

Quite where he obtained a pistol and ammunition from within the most secure part of one of the most secure prisons in the country has never been fully established, but obtain them he did. He later claimed he received the weapon and ammunition from a fellow condemned inmate who had already walked through the dreaded ‘Green Door.’ Detectives felt that relatives had smuggled them in during a visit, but this was never proved. Whatever the source, Scillitano was now armed.

And extremely dangerous.

Not something on any prisoner's list of approved items, especially not a condemned murderer.

Not something on any prisoner’s list of approved items, especially not a condemned murderer.

Days before his scheduled execution, late on what should have been one of the last nights of his life, Scillitano took his chance. He started by shooting Guard Daniel McCarthy and leaving his body in Scillitano’s cell. Dashing through the execution chamber (knocking over ‘Old Sparky as he went) he headed straight for a door in Sing Sing’s outer wall normally used by guards and by witnesses leaving after an execution. It opened right from the prison wall near the Death House directly onto the bank of the Hudson River.

While guards scrambled to arm themselves and respond quickly to the break attempt Scillitano wasted no time. He did almost waste Guard Nichols and Guard Bullard, both of whom were fortunate to survive his shooting them, scrambled down the river in a hail of bullets, threw himself into the water and was gone.

Injured during the break, Scillitano staggered into the Ossining General Hospital. Having heard the siren, the night attendant was immediately suspicious when the bedraggled, soaking-wet stranger appeared before her in the small hours of the morning. Stalling for time, she took her time attending to his injuries. She also discreetly alerted the authorities who promptly arrived, disarmed Scillitano and arrested him. Having managed the almost-unmanageable, Scillitano had blotted his copybook by being caught after only a couple of hours of freedom.

Given the murder of Guard McCarthy, on June 29, 1916 Sing Sing Warden James Osborne personally requested that Charles Whitman (the same Charles Whitman who, as District Attorney, had sent Scillitano to the Death House) issue a stay of execution so he could be tried for McCarthy’s slaying. Whitman, as tough a Governor as he’d been a DA, firmly refused. Scillitano would walk his last mile as scheduled at 6am on June 30, 1916.

He did, amidst a blaze of media publicity and public interest. Normally Sing Sing’s death chamber held a maximum of 12 witnesses (including reporters, New York law requiring executions to be witnessed by the press). For Scillitano the rule was rescinded and the death chamber was standing room only.

Where Scillitano's story ended, the original Sing Sing death house.

Where Scillitano’s story ended, the original Sing Sing death house.

Escorted into the chamber by the Chaplain Father Cashin and by four guards instead of two, with two in front of him and two behind, Scillitano was somber and quiet as he took his final seat. His final words were brief and to the point:

“Goodbye, and God bless you all.”

Hurlburt and the guards applied the electrodes and secured the heavy leather restraining straps. All was ready and Hurlburt crossed the chamber to the alcove containing the switchboard. At a silent signal from Warden Osborne, Hurlburt took a final look at the strapped, hooded figure and threw the switch at 6:01am.

Oresto Scillitano, alias Oreste Schillitoni, Harry Shields, the ‘Paper Box Kid’ and several other names, was dead.