Real estate mogul Dan Gilbert's downtown Detroit skyscraper is proposed to rise another 100 feet. : Real estate mogul Dan Gilbert's downtown Detroit skyscraper is proposed to rise another 100 feet. Detroit businessman Dan Gilbert plans to break ground soon on the tallest building in Detroit. But history suggests that plans for 'tallest towers' may herald the coming of a recession. JC Reindl, Detroit Free Press An updated rendering from September 2017 of the proposed building on the Hudson's site in downtown Detroit that will be built by Bedrock and designed by SHoP Architects.