In the 1914 case of Willoughby v. City of Chicago, the U.S Supreme Court ruled in favor of the city, upholding its right to regulate and restrict billboards for aesthetic and safety reasons. The plaintiff, Mr. Willoughby owned a billboard company and challenged an ordinance that limited where billboards could be erected within city limits as it affected his business adversely. He argued this was an infringement on his Fourteenth Amendment rights - specifically those protecting life, liberty or property without due process of law; however, the court disagreed with him stating that such regulations were within a municipality's police power if they promoted public welfare including preserving beauty in urban areas.

In the dissenting opinion for Willoughby v. City of Chicago, Justice Holmes disagreed with the majority's decision to overturn a lower court ruling that had upheld a city ordinance regulating billboards. He argued that cities have the right to regulate their own aesthetics and safety standards without interference from federal courts unless there is clear evidence of constitutional violation. According to him, aesthetic considerations are legitimate factors in urban planning decisions and should not be dismissed as trivial or unimportant. Furthermore, he contended that it was not within the purview of Supreme Court justices to substitute their judgment for local officials who were more familiar with specific community needs and conditions. In his view, if every regulation affecting property values could be challenged on due process grounds then virtually all zoning laws would become unconstitutional overnight which would undermine municipal governance across America.