A midcentury painter’s spooky and foreboding view of the Octagon on Blackwell’s Island

By the time Hell’s Kitchen–born George Picken painted this image of darkness and isolation over the Octagon on Roosevelt Island around 1940, the island’s name had been formally changed to Welfare Island.

Picken must have known this. Perhaps he’s setting his painting in the 19th century, when this spit of land known as Blackwell’s Island served as a dumping ground for the city’s poor, criminal, insane, incurably ill, abandoned, and others deemed to be cast-offs from proper society.

The Octagon, built in 1834 by architect Alexander Jackson Davis, became the main entrance of the Lunatic Asylum from 1837 into the early 1900s. This is the same deplorable “madhouse” Nellie Bly exposed in a sensational article series published in the New York World in 1887, which led to reform and ultimately the shutting down of the facility.

Picken captured a piece of Blackwell’s Island backlit with an ominous vibe. He casts light on the rocks by the East River shore, and there’s a yellow glow from the windows of the building behind the Octagon.

The light gives the scene a haunted feel. A red lighthouse in the foreground adds depth and dimension to the painting. It’s almost like a boundary line between the viewer and the dangers of Blackwell’s Island—or between sanity and madness, between being part of society or one of the discarded.

Hmmm, what would Picken think if he knew that the Octagon would become part of a new high-end “apartment community” on what would be renamed Roosevelt Island?