A real estate tycoon known for his risky investments and whole neighborhood developments has passed away. Paul Milstein was 88.

Milstein, who died in his home in New York City, was ranked 237th on Forbes’ world list of billionaires with a net worth of $3.8 billion. His career gave birth to 50,000 apartments, 8,000 hotel rooms, and 20 million square feet of office space. He was also responsible for some luxury buildings near the Lincoln Center.

New Yorkers will probably remember Milstein for his bold investments, including the demolition of the New York Biltmore Hotel in 1981. His group rehabilitated the city’s “rundown” areas of Battery Park City, lower Harlem, and Times Square. In fact, his purchase of the then boarded-up Lincoln Hotel in 1978 was seen as the turnaround of Time Square. He rebranded it as Milford Plaza. “’We felt we made a contribution to the city of New York by redeveloping that entire rundown area,” Milstein was quoted as saying.

Milstein is the son of a Russian immigrant who came to Bronx in 1919. His father started a business on refinishing floors. Paul and his brother eventually moved to construction, building the Dorchester Towers. Their partnership was seen as a total success, with Seymour charming bankers and Paul dealing with the construction. Seymour died in 2001.

The real estate mogul is also a known philanthropist. His family funded a Paul Milstein Hall currently being constructed at Cornell University.

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