In the United States, the Executive branch possesses virtually unbridled classification authority to keep information from the public. Although the Freedom of Information Act and whistleblower protection laws serve as some check on the Executive’s power over national security information, these tools remain largely ineffectual. Because the desire for tight information control competes with the demands of newsgathering, a “game of leaks” has developed among government officials and reporters in which the press alternatively serves as lapdogs, watchdogs, and scapegoats for the Executive branch. This Article demonstrates that the government has been communicating information to the public through leaks ever since the administration of President Theodore Roosevelt. Legal developments in the current climate, including the on-going prosecution of two lobbyists for violations of the Espionage Act in the American-Israeli Public Affairs Committee case, have the potential to establish precedents that could pose dire consequences for this crucial information flow. This Article scrutinizes the constitutionality of prosecuting the non-government parties for the publication of classified information by examining the long and complicated history of the relationship between the press and the Executive branch and the role leaks play in the dissemination of classified information to the public today. After examining the relationship between the press and the Executive branch as well as tracing the development of the reasoning behind the applicable First Amendment doctrine, this Article ultimately argues that in any prosecution against a non-government actor for disseminating national security information, the government must demonstrate that the disclosure posed an immediate and direct threat to national security, but also that the offender either intended the disclosure to harm the United States or help a foreign nation, or that the offender was recklessly indifferent to the harm that the disclosure would cause. Given that the Executive branch has so much power to control the dissemination of national security information to the public, and itself leaks information to support its agenda, its power to punish the publication of leaks must be extremely limited. An intent requirement is consistent with the Supreme Court’s free speech jurisprudence and helps achieve this goal. An intent requirement will encourage the government and the press to continue their historical cooperation when the publication of certain information poses a possible threat to national security interests. It will create an incentive for the government officials to explain their national security concerns to the press, and will simultaneously hold the press accountable for any reckless disregard shown to genuine threats. This approach seeks to strike the proper balance between the Executive’s vast ability to control the dissemination of national security information to the public—often through calculated leaks—and the need to maintain the secrecy of information that is truly sensitive.