How it happened: Doug Harmon and Leona Helmsley

Broker’s relationship with the “Queen of Mean” was transformative for his career
May 23, 2019 04:30PM

Doug Harmon (Credit: Cushman & Wakefield)

Doug Harmon (Credit: Cushman & Wakefield)

In the late 1990s, when Cushman & Wakefield’s Doug Harmon was still a fairly anonymous broker at Eastdil Secured, a man at a dinner party in Anguilla let him know that Leona Helmsley wanted to sell a $5 billion portfolio of property she inherited from her husband, Harry. His career has never been the same.

Details about Harmon’s relationship with the infamous “Queen of Mean” came out in a new Financial Times profile on the mega-broker, who recently sold 450 West 15th Street for the fifth time in his career. (The property went to Google this time for $600 million, 100 times its 1996 sales price.)

Helmsley’s reputation for being unpredictable and difficult meant that Eastdil did not even want her business, despite how valuable her properties were, so Harmon established a separate division in the firm to handle her buildings. He also gave Helmsley her dog, a Maltese named Trouble, who she would famously leave $12 million to upon her death.

Harmon frequently went with Helmsley to the Four Seasons restaurant, where she would regularly demand that he give her $10 bills to tip the bathroom attendant. Eventually, he realized this money was not going where she said it was.

“It was a training ground for the craziness that exists in real estate,” he told the Times.

Harmon’s work with Helmsley launched him into a new tier of buyers and sellers at the same time as real estate was becoming a more mainstream industry, factors that helped turn his career into what it is today.

“In the mid-90s, real estate became an industry that everyone was interested in,” he said. “It’s money, it’s the power, it’s everything—and then you get New York.” [FT] – Eddie Small