He started his career as a Lawyer and eventually a partner in the Chicago law firm of Mayer, Brown & Platt. In 1969, he co-founded JMB Realty with Judd Malkin. He serves as a Managing Partner of Walton Street Capital and Lamb Partners. He is also President of the ALP Liquidating Trust and the Northbrook Corporation, and Chairman of the Board of HSP Gaming and the Falls Management Company. He owns the Holdings Acquisitions Co.. He is a former Co-Chairman of the Board of Urban Shopping Centers. He is Chairman of the Board of Midwest Gaming & Entertainment which owns casinos in Vicksburg, Mississippi, the Rivers Casino in Pittsburgh, Philadelphia, Rivers Casino in Des Plaines, Illinois, and Casino Niagara in Niagara Falls, Canada.