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“important component of the reasonableness inquiry.” 214 Others include the nature of the
information collected, the privacy interest that attaches, and the government interest in the
collection.

(U) In conducting this analysis, courts assess whether a proposed investigatory activity
was reasonable given what the government knew at the time, rather than with the benefit of
hindsight. In other words, rather than assess the success of a particular wiretap or a particular
program based on what the government discovered, a court conducts a reasonableness analysis
by placing itself in the shoes of a government investigator at the time of the government
“search.” As then-Judge Scalia put the point, “just as ‘a search is not to be made legal by what it
turns up,’ the fact that, ex post, a wiretap is seen to have been unsuccessful in developing
national-security information does not establish that, ex ante, it was not reasonable to conduct it
for that purpose.” 215 Similarly, then-Judge Ruth Bader Ginsburg explained “[t]hat probable
cause may have been absent when viewing the arrest ex post does not in and of itself establish
that the officer acted in an objectively unreasonable manner ex ante.” 216 Indeed, the contrary
rule would mean that every government search that was lawfully predicated at the time would
ultimately be “unreasonable” if it failed to discover evidence related to a crime or foreign
intelligence. On that logic, every time the government properly elected, as a matter of sound
policy, to shut down a program, the program would become unconstitutional because the
government had effectively conceded that the program’s costs outweighed its benefits. 217

214 (U) Mohamud, 843 F.3d at 443.
215 (U) Smith v. Nixon, 807 F.2d 197, 203 (D.C. Cir. 1986) (quoting United States v. Di Re, 332 U.S. 581, 595
(1948) (footnote omitted)).
216 (U) Martin v. Malhoyt, 830 F.2d 237, 263 (D.C. Cir. 1987); see also Anderson v. Creighton, 483 U.S. 635, 639
(1987) (observing that the relevant Fourth Amendment inquiry is whether “in the light of preexisting law the
unlawfulness” of government action was “apparent” and describing the question as an “objective (albeit fact-
specified) [inquiry into] whether a reasonable officer could have believed” action was legal). For other cases using a
similar approach in a variety of Fourth Amendment-related circumstances, see Bruce v. Guernsey, 777 F.3d 872 (7th
Cir. 2015) (“Guernsey also argues that the fact that Bruce was ultimately admitted to the hospital and later
involuntarily committed to a behavioral health center for three days demonstrates that he had probable cause to seize
her. But the Fourth Amendment requires an ex ante, not an ex post, analysis.”); United States v. Green, 560 F.3d
853, 857 (8th Cir. 2009) (rejecting ex post analysis regarding whether a particular dresser could completely conceal
a person).
217 (U) That is why we focus on the perspective of those who established the CDR program. As for “whether an
extension of that authority would be constitutional in light of the facts and circumstances known today,” Statement
of Ed Felten and Travis LeBlanc at 71, we do not believe that a statute enacted by Congress to reauthorize the CDR
program would be “facially” unreasonable, and hence unconstitutional, under the Fourth Amendment. The Court
has made clear that “claims for facial relief under the Fourth Amendment”—direct attacks on the constitutionality of
a statute, as opposed to the statute’s application to a particular set of facts—“are unlikely to succeed when there is
substantial ambiguity as to what conduct a statute authorizes.” City of Los Angeles v. Patel, 135 S. Ct. 2443, 2450
(2015). That is because, to succeed on such a facial challenge, a “plaintiff must establish that a law is
unconstitutional in all of its applications.” Patel, 135 S. Ct. at 2451 (emphasis added, quotation marks

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