In the case of Hannegan, Postmaster General v. Esquire, Inc., 1945, the United States Supreme Court ruled in favor of Esquire Magazine after it was denied second-class mailing privileges by Robert E. Hannegan as Postmaster General. The denial was based on a claim that the magazine failed to meet educational standards set for such mailings and contained content deemed "morally improper". However, the court found that this decision overstepped boundaries set by Congress regarding what could be considered mailable matter under second-class postage rates. It held that only Congress had authority to determine whether or not certain types of publications should be excluded from these benefits due to their content or character; thus ruling against censorship powers being exercised by postal authorities without explicit legislative sanction.

In the dissenting opinion for Hannegan v. Esquire, Inc., Justice Frankfurter disagreed with the majority's interpretation of Congress' intent in granting discretionary power to the Postmaster General regarding second-class mail privileges. He argued that this discretion was intended to prevent misuse of postal subsidies by publications not primarily designed for public information or education but rather commercial exploitation. The justice believed that Esquire magazine fell into this category due to its focus on entertainment and advertising content over educational material. Therefore, he contended that it should be within the Postmaster General’s authority to revoke their second-class mailing privilege if deemed appropriate under these considerations.