In the 1918 case of Benedict v. City of New York, the United States Supreme Court ruled in favor of the city. The dispute arose when a property owner, Mr. Benedict, challenged an assessment for local improvements made by the city on his properties located within its limits. He argued that he was being unfairly taxed because these improvements did not increase his property value to match or exceed what he was being charged for them; therefore, it violated his constitutional rights under Fourteenth Amendment's due process clause and equal protection clause. The court rejected this argument stating that as long as there is some benefit conferred upon a property by public improvement works - even if it doesn't directly translate into increased market value - then such assessments are constitutionally permissible and do not violate any right protected by Fourteenth Amendment. Furthermore, they clarified that how much benefit has been received from such improvements is largely left up to legislative discretion rather than judicial review unless there's clear evidence showing gross inequality or injustice.

In the dissenting opinion for Benedict v. City of New York, Justice Holmes disagreed with the majority's decision to uphold a tax on stock transfers. He argued that this type of taxation was unconstitutional because it interfered with interstate commerce and violated the Due Process Clause of the Fourteenth Amendment. Holmes believed that stocks were not merely local property but instruments of commerce, thus making them subject to federal jurisdiction rather than state or local taxation laws. Furthermore, he contended that taxing stock transfers could potentially lead to double taxation if multiple states attempted to levy taxes on transactions involving the same shares. This would be unfair and burdensome for shareholders who might have no connection whatsoever with some jurisdictions imposing such taxes.