One of Brooklyn’s first penitentiary institutions, or more simply, its first prison, was established in the mid-19th century. In 1846, the Kings County Board of Supervisors purchased a plot of land bordered by Rogers and Nostrand Avenues, Carroll and Montgomery Streets. At the time, this was a sparsely populated area, overgrown with brush.
This land originally belonged to Dutch settlers in the early 1600s, passing through multiple hands over the centuries, often owned by wealthy families.
More details on how Brooklyn’s first prison was built and what happened to it can be found on brooklyn-future.com.
Brooklyn’s First Prisons
On this land, the city constructed a prison facility and a workhouse, enclosed by a high stone wall.
The Kings County Penitentiary housed serious criminals, while the workhouse detained people convicted of minor offenses. Both men and women served their sentences there, but they were housed in separate wings of the facility.
The workhouse included a shoe factory, where many inmates—both men and women—worked.
Male prisoners wore black-and-white striped uniforms. Many of them were gang members involved in street robberies in Brooklyn. These individuals were commonly referred to as “crows,” which eventually led to the entire area being called Crow Hill.
It should be noted that no prison in 19th-century America was comfortable, but even among them, the Kings County Penitentiary stood out—for the worse.
Prison officials and guards were accused of negligence, unprovoked cruelty, and aggressive behavior toward inmates, as well as maintaining inhumane conditions.
Ultimately, in 1906, Kings County sold the prison to the Catholic Church, which in turn sold it to the Society of Jesus (Jesuits). The Jesuits intended to build a large educational campus, which would include a college, a preparatory school, and a gymnasium.
In 1907, the old prison was demolished, and the foundation stone for Brooklyn College and the preparatory school was laid.
By 1913, the college was closed, and the school was restructured into Brooklyn Academy.
Later, the institution was renamed Brooklyn Preparatory School, becoming a boys’ high school.
Over time, the entire site of the former prison was transformed into a school complex with classroom buildings and sports fields. These facilities produced many notable graduates, including William Peter Blatty (author of The Exorcist), Joseph Califano (former U.S. Secretary of Health, Education, and Welfare), and college football coach Joe Paterno.
The school maintained a strong academic reputation until its last graduating class in 1972.
Raymond Street Jail
By the late 1960s, the Jesuits were forced to merge their schools due to rising costs and declining enrollment.
By 1968, they knew the school would have to close, and in 1971, they sold the Brooklyn Prep campus to the City University of New York (CUNY) for $2.75 million.
Thus ended the story of Brooklyn’s first prison, but not of penitentiary institutions in the borough.
Another notorious Brooklyn jail was located on Raymond Street. It was widely known for its brutal conditions.
The prison’s cornerstone was laid in 1836—by the prisoners themselves.
Over the years, the facility underwent multiple expansions and renovations.
By 1879, the Raymond Street Jail resembled the West Point Fortress, which served as its architectural inspiration.
The main building housed male inmates, while a separate annex held female prisoners.
The women’s building was later demolished and rebuilt in 1911.
From the beginning, this penitentiary was poorly planned and chronically overcrowded.
To illustrate how carelessly it was designed, during one of its final renovations, architects forgot to include entrance doors.
As a result, the main entrance had to be carved into the wall after construction had already begun.
It seemed as though the designers intended for no one to ever leave.
Conditions inside the Raymond Street Jail were medieval—there was no proper lighting, tiny cells, unsanitary conditions, and extreme overcrowding.
After years of efforts to shut it down, the city finally closed it permanently in 1963, replacing it with the modern Brooklyn House of Detention on Atlantic Avenue.
The Transformation of Raymond Street
The Brooklyn Hospital, located next to the jail, later expanded northward and, in 1976, constructed the 19-story Maynard Building on the former prison site.
Even Raymond Street itself ceased to exist—it was renamed Ashland Place.
Brooklyn House of Detention
The new Brooklyn House of Detention on Atlantic Avenue was built in 1957, designed to house 800 inmates.
Interestingly, plans for its construction date back to 1948–1949.
However, delays in budget approvals and project details stalled construction.
By 1950, just as everything was finalized, the Korean War began, prompting the U.S. government to redirect resources elsewhere.
As a result, construction of the Brooklyn House of Detention for Men was postponed.
Even after it was completed, the Brooklyn House of Detention was not used as originally intended.
Instead of housing pretrial detainees from Kings County, the facility served as a shelter for teenagers from all five boroughs of New York City for nearly 12 years (from January 1957 to September 1968).
Bill de Blasio’s Prison Reform Plans
In January 2018, New York City Mayor Bill de Blasio announced a 10-year plan to close the Rikers Island prison complex and relocate inmates to four new jails closer to courthouses, families, and legal representation.
This plan was based on recommendations from the independent Lippman Commission, whose 2017 report condemned conditions at Rikers Island.
One of the new jails was planned on the site of the Brooklyn House of Detention, which was deemed outdated and not compliant with modern correctional standards.
For example, inmates suffered from extreme heat, particularly in recent years, prompting authorities to allocate funds for air conditioning.
City officials stated that the new jails would be designed more humanely, making it easier for detainees to remain connected to the legal system and their families.
In 2020, the city closed the Brooklyn House of Detention as part of de Blasio’s prison reform strategy.
The approximately 390 inmates housed there were transferred to other facilities, including the Manhattan Detention Complex and the Vernon C. Bain Correctional Center, a floating prison barge near the Bronx.
Most staff from the Department of Correction were also relocated, except for a small team of about 10 employees, who remained to maintain administrative operations, oversee bail processing, and secure the vacant facility.