Sing Sing’s Death House – 1891 to 1963.


Sing Sing. The name alone implies bad conditions, violence, fear, poor food, hard labour, harder punishments, misery and death. Even the name itself suits a prison, coming from the Native American phrase ‘Sinck Sinck’ meaning ‘Stone upon stone.’ Movie fans may remember James Cagney’s ‘Angels with Dirty Faces’ where screen gangster ‘Rocky Sullivan’ (inspired by … Continue reading Sing Sing’s Death House – 1891 to 1963.

On This Day in 1893 – Morphine murderer Carlyle Harris, his last mile and his last laugh.


When Buchanan entered the condemned cells at Sing Sing he was probably a little embarrassed to finally meet the 'stupid amateur' and 'bungling fool' he'd so disastrously mocked. Buchanan had had the first laugh. Harris laughed last and longest, but had little time left to do it.

On This Day in 1926 – Gerald Chapman, America’s first ‘Public Enemy Number One.’


“Death itself isn’t dreadful, but hanging seems an awkward way of ending the adventure…” – Gerald Chapman to his lawyers after being condemned to hang for murder in 1925. ‘Gerald Chapman’ was his favorite alias, but his real name was probably George Chartres. Given that records are sketchy and Chapman was always evasive about his youth, … Continue reading On This Day in 1926 – Gerald Chapman, America’s first ‘Public Enemy Number One.’

1954, a mass break-out from Sing Sing’s Death House (almost) and Sing Sing’s last ‘triple-hitter.’


Rosario, believing he had done enough to catch the right eyes, awaited his clemency and heard nothing. There was no more ominous silence than when a Governor was considering clemency, it usually meant there wouldn't be any.

Thomas Tobin and Sing Sing’s Death House, the prison he built for himself.


If the worst prisons are those we make for ourselves Thomas Tobin couldn't have constructed anywhere more hideous.

On This Day in 1925 – John Hurlburt performs his last execution. ‘Yellow Charleston’ has his last dance.


A few years ago I covered the story of John Hurlburt, New York's second 'State Electrician.' Trained by predecessor Edwin Davis, Hurlburt executed 140 prisoners during his tenure. Hurlburt's official debut was executing George Coyer and Giuseppe DeGoia at Auburn Prison on August 31 1914. Unofficially he had already executed prisoners under Davis's supervision. As … Continue reading On This Day in 1925 – John Hurlburt performs his last execution. ‘Yellow Charleston’ has his last dance.

Frank Rimieri, Adolph Koenig and Doctor Allan Mclane Hamilton – A dark day that cast a very long shadow…


When Frank Rimieri and Adolph Koenig rode the lightning at Sing Sing on 20 February 1905 that was nothing unusual in itself. First used on William Kemmler on 6 August 1890, New York's electric chair was already seeing regular use. Single and double executions like this one were standard practice and New York, already enthralled … Continue reading Frank Rimieri, Adolph Koenig and Doctor Allan Mclane Hamilton – A dark day that cast a very long shadow…

On This Day in 1890 -Martha Place, the first woman in the electric chair.


A free chapter from my book 'Murders, Mysteries and Misdemeanors in New York,' available now. Like many countries the US has an at times contradictory attitude to its death penalty, no more so than when a woman faces execution. Women account for fewer than 5% of death sentences in the US and less than 1% … Continue reading On This Day in 1890 -Martha Place, the first woman in the electric chair.

On This Day in 1932, Michael Malloy – The Man Who Would Not Die


They had started with the obvious: alcohol. That should have been a simple, effective means of their victim destroying himself rather than the Trust taking the additional risk of actually murdering him. Insurance fraud was not a capital offence then or now; first-degree murder no longer is in New York State, but in 1932, it certainly was. The 1920s and 1930s was the busiest period for New York’s electric chair, averaging around twenty executions every year. If choosing Malloy was a bad idea, then actually murdering him was even worse.

On This Day in 1927 – Paul Hilton, Antonio Paretti and the finale of the Mafia-Camorra War.


Double executions were no rarity at Sing Sing, especially in the Roaring Twenties. Prohibition and the Jazz Age saw an unprecedented number (125 men and a few women) walk their last mile in the Empire State. That trend would peak in the 1930’s (153) before decreasing in the 1940’s (114) and decline further in the … Continue reading On This Day in 1927 – Paul Hilton, Antonio Paretti and the finale of the Mafia-Camorra War.