In the 1917 case of Sears, Trustee v. City of Akron, the United States Supreme Court ruled in favor of the city. The dispute arose over a piece of land that was originally owned by Mr. Sears but had been taken over by the city for public use as part of a street improvement project without compensation to Mr. Sears on grounds that he would benefit from increased property value due to improvements made around his remaining property. However, when it became apparent that no such increase in value occurred and instead resulted in financial loss for him, Mr. Sears sued for compensation arguing violation of his constitutional rights under Fourteenth Amendment's Due Process Clause which prohibits deprivation "of life, liberty or property without due process". The court held that while generally government must pay just compensation when private property is taken for public use (eminent domain), exceptions exist where benefits are conferred upon owner through improvements made around their remaining properties offsetting any losses incurred - known as 'special assessments'. In this case however since there were no actual benefits realized by Mr.Sears despite initial claims,the court concluded it was an error not compensating him initially but didn't order any payment because he failed to challenge assessment at time it was levied.

In the dissenting opinion for Sears, Trustee v. City of Akron, Justice Holmes argued that the city had not violated any constitutional rights by passing an ordinance to regulate billboards. He believed that such regulation was within the power of local governments and did not infrally upon property rights or freedom of speech. The justice contended that a billboard is a structure subject to municipal control like any other building in terms of safety and aesthetics considerations. Furthermore, he asserted that there was no contractual obligation between the city and billboard owners which could be impaired by this law as claimed by majority justices; rather it's just an exercise of police powers for public welfare.