Penn South was sponsored by the International Ladies' Garment Workers Union based on a cooperative model promoted by the United Housing Foundation.
[3] The New York City Committee on Slum Clearance recommended Penn Station South for federal funding in August 1956.
[9] The UHF's president, Abraham Kazan, later called the preservation a "mistake" because it had prevented Penn South from being developed earlier.
[13] Groups of residents also organized picket lines and filed affidavits that attested to the hardships caused due to their relocations.
[14] In another act of protest, tenants living in the future Penn South site withheld rent payments to the ILGWU, their new landlord.
[22] Early on in the construction process, supporters of Penn South wanted to include "Chelsea" in the name, in order to better integrate it with the surrounding community.
President John F. Kennedy addressed the workers on the project, with former First Lady Eleanor Roosevelt and New York Governor Nelson Rockefeller in attendance.
[30][31] That October, some tenants were prevented from moving into their units due to a union dispute regarding sink installations.
A New York Times article published that year said that Penn South was "widely regarded as one of the best-run cooperatives in the state".
[42] In 2014, Penn South's management opened up a lottery system in which it randomly distributed some vacant apartments to applicants who met specified criteria.
[25] The possibility of Penn South generating its own power had been proposed as early as 1960, before the development had opened, due to disagreements with utility provider Consolidated Edison over electricity rates.
[50] To help keep Penn South affordable to those with limited incomes, New York City gave the development a 25-year tax abatement between 1961 and 1986.
[36] A further adjustment was made when the development asked the city in 1999 for tax relief when the building boom in Chelsea caused the project's assessed value to skyrocket.
The city responded in 2001 by allowing the development's taxes to be calculated based on the cooperative's income, as is done with Mitchell-Lama housing.
Under the terms of agreements reached with the City of New York in 2002, and separately with the United States Department of Housing and Urban Development, Penn South's eligibility for tax abatements offered by Mitchell-Lama was extended to 2052.
[36] In February 2017, the New York City Council extended Penn South's tax abatement to 2052, ninety years after the development's opening.