Macklowe quickly transitioned from broker to builder. Keenly interested in architecture and modern art, he soon became known for developing sleek modernistic buildings like the Metropolitan Tower and for his starkly white minimalist offices. His firm, Macklowe Properties, owns or has owned a number of New Yorklandmarks including 400 Madison Avenue, 540 Madison Avenue, the historic Drake Hotel and Two Grand Central Tower. In 1985, Macklowe was fined $2 million for ordering the late-night demolition, without a permit, of four buildings, including a welfare hotel, in Times Square. In 2003, he made his mark by purchasing the General Motors Building for a record price of $1.4 billion. The value of the skyscraper soon doubled, thanks in part to his persuading Apple to build a subterranean Apple retail store beneath the building's plaza, an idea he personally and successfully pitched to Steve Jobs. Jobs then proposed that the entrance to the sunken store be a 32-foot all-glass cube, which the city approved and was opened to the public in 2006. In February 2007, during the peak of the real estate market, Macklowe purchased seven Manhattan skyscrapers for $6.8 billion from the Blackstone Group. He used $50 million of his own money and financed the rest with $7 billion in short-term loans from Deutsche Bank and the publicly traded hedge fund the Fortress Investment Group. In early 2008, he failed to refinance a $5.8 billion loan from Deutsche Bank and lost all seven buildings. Among the buildings forfeited were the General Motors Building and the Credit Lyonnais Building.
Personal life
On January 4, 1959. Macklowe married Linda Burg. After over 50 years of marriage in 2016, Burg filed for divorce. In 2019 after a contentious, $2 billion divorce, he remarried to Patricia Lazar-Landeau. Macklowe put a massive picture of himself and his new wife on the corner of a building he owns in Manhattan, in what was widely seen as an insult to his former wife. The Macklowes have two children: William S. Macklowe and Elizabeth Macklowe. William replaced his father as President of Macklowe Properties in 2008. He and his wife belong to the Jewish Center of the Hamptons synagogue. In 1993, William married and divorced the Americanfashion designerTory Burch. In 2004, William married Julie Lerner in a Jewish ceremony at the Metropolitan Club in New York City. Elizabeth was married to and divorced from Kent Swig, son of fellow real estate developer Melvin Swig.