The firm subsequently renamed Leopold Property Consultants, became one of the largest [citation needed]companies in North America to represent only tenants.
In May 1986, while representing Coopers & Lybrand (today PricewaterhouseCoopers), Clarkson Tetrault (today McCarthy Tétrault), and Claridge Investments (the holding company for the descendants of the late Samuel Bronfman), Leopold inspired the redevelopment of one of downtown Montreal's most important heritage sites, The Windsor Hotel.
His leadership in the real estate industry, coupled with his well-publicized association with Prime Minister Brian Mulroney (1984–1993), brought Leopold into the spotlight in the Canadian press.
[3] In 1993 Leopold relocated to New York City to pursue large scale property development in Manhattan.
One of Leopold's largest development transactions included conceiving and creating nearly two acres of food courts in the World Trade Center.
Leopold has served on the Boards of Directors of the University Club of Montreal, the Edmonton Art Gallery, Ruby Foo's Restaurant and Hotel, the Montreal Alouettes of the Canadian Football League, the Canadian Guild of Crafts, and the Board of Governors of the Roosevelt Institute which in partnership with the National Parks and the National archives is responsible for the maintenance of the birthright grounds, home and Presidential library of President Franklin Delano Roosevelt.