Leonard Steinberg

Leonard Steinberg is a polarizing figure. 

After more than a decade at Douglas Elliman, Steinberg was at the top of his game, running the firm’s leading team in Downtown Manhattan. In 2013, he sold a townhouse in Tribeca for $43 million and was one of the brokers behind the $32 million sale of Dolce & Gabbana designer Domenico Dolce’s penthouse on 11th Avenue in 2009. 

Then in 2014, he announced a major shakeup: Steinberg would jump to Compass, then just a two-year-old brokerage. The move shocked many in the industry. Compass was (and still is) a controversial company. Backed by millions in venture capital funding, the firm marketed itself as a break from the traditional brokerage, a quasi-tech company that promised to change the future of real estate transactions. 

Now more than 10 years later, he’s become a major figurehead at Compass (with a vanity title to boot) and a vocal supporter of its CEO Robert Reffkin’s campaign against policies requiring agents to upload properties on multiple listing services and listing syndicators within one day of public marketing. Last year, his team placed seventh in The Real Deal’s ranking of the top brokers in New York City, with more than $150 million in sales.

He’s been a vocal critic of real estate-focused reality TV, going so far as to say at last year’s TRD New York Forum, “If I was a woman, I would feel extremely disappointed,” earning him consternation from some front-facing female brokers.

— Sheridan Wall