In 1981, President Reagan issued Executive Order (E.O.) 12,333, which has since come to serve as a general charter for mass intelligence surveillance. Despite 12,333’s importance in conducting surveillance, questions abound surrounding the full extent of the executive branch’s programs under the order.
Last year, the MFIA Clinic helped the ACLU launch FOIA litigation to learn more about the operation of E.O. 12,333 in practice. The litigation seeks documents that would detail surveillance programs and policies under E.O. 12,333. In response to the suit, the government produced several responsive documents with heavy redactions and withheld other records entirely. The Southern District of New York upheld these redactions, and the ACLU is now appealing the decision to the Second Circuit.
Increased disclosures about the workings of E.O. 12,333 and surveillance conducted thereunder is particularly important because it would reduce the “chilling effect” that surveillance has on free speech. First introduced into First Amendment jurisprudence by Justice Frankfurter in a concurrence in Wieman v. Updegraff, the chilling effect “occurs when individuals seeking to engage in activity protected by the First Amendment are deterred from so doing by governmental regulations not specifically directed at that protected activity.” In other words, chilling effects unduly inhibit individuals from exercising their First Amendment rights.
Over the past several decades, Supreme Court doctrine has singled out laws and policies that are overbroad and highly discretionary in their implementation as producing the greatest chilling effects. The logic behind the effect is simple: “[I]f a law or regulation is unclear so that speakers cannot determine whether their speech is or is not covered, speakers may self-censor themselves to avoid the risk of liability.” When laws are too ambiguous, individuals inhibit their enjoyment of First Amendment rights due to uncertainty over what expressions will have legal repercussions. In fact, the Court has recognized that the broader or vaguer a law is, the greater the extent to which it will deter free speech. Indeed, “[t]he mere existence of a vague or overbroad statute can create a chilling effect irrespective of the manner in which it may be applied.”
Consequently, the Court has struck down statutes as too vague or broad because of the chilling effect these laws produced. In the 1965 case Dombrowski v. Pfister, for example, the Court granted an organization active in fostering civil rights for minorities injunctive relief against a threatened criminal prosecution under the Louisiana Subversive Activities and Communist Control Law and the Communist Propaganda Control Law. Specifically, the Court held that “the existence of a penal statute susceptible of sweeping and improper application” chilled the expression of First Amendment rights. Statutes granting the government too much leeway in enforcement increases uncertainty and thereby amplifies chilling effects.
The government’s authority to conduct surveillance—particularly in the context of E.O. 12,333, which, unlike programs under the Foreign Intelligence Surveillance Act, is not subject to oversight or court review—is notoriously broad and discretionary, operating almost entirely at the executive branch’s will. As the ACLU and MFIA demonstrated in their briefing documents, and as many other national security experts have argued, we don’t know much about programs under E.O. 12,333. Knowledge of how much data is being swept, how this data is used, and how the NSA and other government agencies interpret their power under E.O. 12,333, among other questions, remains inexact at best.
The chilling effects of mass government surveillance programs are well demonstrated—and even quantified—in scholarly literature and case law alike. Recent studies have also documented the disproportional impact that surveillance-based chilling effects have on minorities, youth, and women. While these chilling effects alone cannot ground constitutional challenges, they do fundamentally erode the enjoyment of First Amendment rights.
This is not to say that these programs are unconstitutional or that the government is abusing its discretion. Rather, these points merely illustrate the degree to which mass surveillance breeds uncertainty by proceeding in an opaque and discretionary way. Consequently, while these programs may not rise to the level of a constitutional violation, their opacity produces chilling effects troubling to First Amendment rights.
Should the ACLU’s appeal succeed, newly released documents could reduce this opacity and help us understand the legal logic behind how the government uses its great discretion. While these documents would only explain the legal interpretations behind E.O. 12,333 programs, and not technical information on how the programs operate, the records would illuminate the workings of E.O. 12,333—and thus help to mitigate any chilling effect by adding greater certainty to the realm of mass surveillance.
 Am. Civil Liberties Union v. Nat’l Sec. Agency, No. 13-cv-09198, 2017 WL 1155910 (S.D.N.Y. Mar. 27, 2017).
 Note, The Chilling Effect in Constitutional Law, 69 Colum. L. Rev. 808, 842 (1969) (citing Wieman v. Updegraff, 344 U.S. 183, 195 (1952) (Frankfurter, J., concurring)).
 Frederick Schauer, Fear, Risk and the First Amendment: Unraveling the “Chilling Effect,” 58 B.U. L. Rev. 685, 693 (1978).
 Free Speech on the Internet—Overview of Modern Free Expression Analysis Under the First Amendment—Overbreadth, Vagueness, and the Chilling Effect on Speech, 2 Internet L. & Prac. § 24:4.
 New York v. Ferber, 458 U.S. 747, 772 (1982) (“While a sweeping statute, or one incapable of limitation, has the potential to repeatedly chill the exercise of expressive activity by many individuals, the extent of deterrence of protected speech can be expected to decrease with the declining reach of the regulation.”)
 The Chilling Effect in Constitutional Law, supra note 7, at 814 (citing Dombrowski v. Pfister, 380 U.S. 479, 486 (1965); Thornhill v. Alabama, 310 U.S. 88, 97 (1940); and Carmichael v. Allen, 267 F. Supp. 985, 994 (N.D. Ga. 1967)).
 John Tye, Meet Executive Order 12333: The Reagan Rule That Lets the NSA Spy on Americans, Wash. Post (July 18, 2014), https://www.washingtonpost.com/opinions/meet-executive-order-12333-the-r....
 Alvaro Bedoya, Executive Order 12333 and the Golden Number, Just Security (Oct. 9, 2014), https://www.justsecurity.org/16157/executive-order-12333-golden-number/.
 See, e.g., Kelsey Cora Skaggs, Surveilling Speech and Association: NSA Surveillance Programs and the First Amendment, 18 U. Pa. J. Const. L. 1479 (2016); Katherine J. Strandburg, Membership Lists, Metadata, and Freedom of Association's Specificity Requirement, 10 I/S: J. L. & Pol'y for Info. Soc'y 327 (2014).
 Jon Penney, Whose Speech is Chilled by Surveillance?, Slate (July 7, 2017), http://www.slate.com/articles/technology/future_tense/2017/07/women_youn....