In the case of Shapero v. Kentucky Bar Association, 1987, the U.S Supreme Court ruled in favor of attorney Robert Shapero who had been prohibited by the Kentucky Bar Association from sending targeted direct mail advertising to potential clients known to need specific legal services. The court held that this prohibition violated his First Amendment rights. The decision was based on a previous ruling (Bates v State Bar of Arizona) which established that lawyer advertising was commercial speech and thus protected under the First Amendment unless it is misleading or pertains to illegal activity. In its judgment, the court stated that there's no substantial difference between a letter and a newspaper ad as far as risk for deception or coercion is concerned; hence if lawyers could advertise in newspapers they should also be allowed to send direct-mail advertisements.

In the dissenting opinion for Shapero v. Kentucky Bar Association, Justice O'Connor argued that the majority's decision failed to recognize a significant difference between targeted direct-mail solicitation and general advertising. She contended that such direct mailings are more intrusive and have greater potential for abuse or overreaching than general advertisements. The justice also pointed out that these types of solicitations could exert pressure on individuals who may be experiencing personal crises or facing legal problems, making them particularly vulnerable to persuasive tactics by lawyers seeking business. Furthermore, she disagreed with the majority's view about state interests in regulating lawyer conduct, arguing states should have broad latitude in setting standards for professional behavior within their borders.