That inconsistency--in both enforcement and in the regulations themselves--was one of the arguments that the outdoor advertising companies, including Clear Channel Outdoor, put forth in challenging the laws, which were devised in 1940 and amended in 2001. The companies, Crotty wrote, charged "that the city enforces its zoning regulations unevenly, and, in certain cases, in a manner that unconstitutionally favors the city in violation of First Amendment speech protections." Furthermore, the judge wrote, the lawsuits charged that "the city's regulatory scheme is riddled with exceptions that undermine its efficacy to the point of unconstitutionality."

Crotty's decision ruled on two separate cases: a consolidated action on separate lawsuits filed by Clear Channel and by Atlantic Outdoor Advertising, Scenic Outdoor, Troystar City Outdoor and Willow Media regarding billboards on arterial highways; and an action by Metro Fuel on its internally-illuminated panel signs. The so-called "Clear Channel plaintiffs" contended that zoning regulations on the size and location of advertising signs near highways are unconstitutional because they do not advance the city's interest in promoting traffic safety and aesthetics. Clear Channel also disputed the constitutionality of the requirement, enacted in'01, that outdoor advertising companies must register all their arterial signs with the city's Department of Buildings. Metro Fuel challenged regulations that prohibit illuminated signs outside of large commercial districts.

Concerning the limits on billboards near highways, Crotty wrote that the exceptions to the regulations do not undermine the laws' effectiveness. Under the'01 zoning resolution, "the Clear Channel Plaintiffs will be forced to remove--or convert to non-commercial copy--dozens of large, distracting billboard signs near arterial highways which should never have been erected in the first place. Billboards belonging to other outdoor advertising companies not parties to this case will presumably also come down."