500 W 42nd Street was the winner of the 1899 Model Fireproof Tenement competition. The building was designed by Ernest Flagg, a well-known architect who built the Singer Building -- one of the earliest skyscrapers in NYC that was torn down in 1968 -- and the Corcoran Gallery. He had a deep interest in better and more efficient tenement design. A proponent of tenement design, he planned and constructed 500 West 42nd Street complex model, originally part of a 12-building complex with 1,100 apartments and included the first use of structural concrete in residential construction in New York City. The complex was partially demolished for the West Side Improvement Project, which relocated the rail line below grade on the West Side. The remaining buildings were owned by the Flagg family through the 1970s.

After the buildings were sold, they quickly fell into distress. In the 1970s through the 2000s, these buildings became the site of some of the worst tenant harassment in Hell’s Kitchen. There was no heat or hot water, sometimes for the entire winter, with frozen pipes and sprinklers. Two elderly tenants died during that period. Eventually, New York City’s Department of Housing Preservation and Development (HPD) made a legal finding of tenant harassment on the site.

A series of developers next owned the buildings, including one who was convicted as part of a City-wide arson-for-hire ring . The mortgage was not paid, and the buildings went into receivership. After continued changes of ownership, the bank that held the mortgages failed. The Federal Deposit Insurance Corporation (FDIC) then took it over, hosted an auction, and sold the buildings to yet another developer. Throughout this series of events, Housing Conservation Coordinators (HCC), a neighborhood tenant advocacy organization, organized and worked with the tenant association to ensure livable conditions. That harassment finding prevented redevelopment without the provision of affordable housing on the site, as part of a Cure for Harassment (Cure) under the Special Clinton District. Throughout the entire period of real estate speculation, every owner sought to demolish the historic buildings on West 42nd street and proposed a market-rate tower.

In 2000, at the invitation of HCC, CHDC worked to develop a plan to relocate the proposed tower to West 41st Street and renovate the historic West 42nd Street tenements to meet the affordable housing harassment requirement. The result was the current project.

The developer would renovate two of the West 42nd Street buildings to meet the Cure requirement for affordable housing, and include 16 additional apartments of permanently affordable housing in the newly constructed tower on West 41st Street to create a zoning bonus for that building. After the long-term tenants moved into the Cure building, the remaining two buildings on West 42nd Street would be donated to CHDC and renovated as supportive housing funded by the City of New York, creating a single building with 91 units of housing affordable to households at 50%, 60%, and 80% of the Area Median Income. The ground floor corner CVS drug store is a commercial condo, and was retained by the developer; the other commercial condo is owned by CHDC is occupied by a barbershop, a coffee shop, and veterinarian.