August Term 2016 Argued: October 25, 2016 Decided: December 20, 2016 Docket Nos.… v. 6 7 UNITED STATES DEPARTMENT OF JUSTICE, including 8 its component the Office of…

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15-2956-cv(L)
American Civil Liberties Union v. United States Department of Justice
UNITED STATES COURT OF APPEALS
FOR THE SECOND CIRCUIT
August Term 2016
Argued: October 25, 2016 Decided: December 20, 2016
Docket Nos. 15-2956(L), 15-3122(XAP)
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AMERICAN CIVIL LIBERTIES UNION, AMERICAN CIVIL 1
LIBERTIES UNION FOUNDATION, 2
3
Plaintiffs-Appellants-Cross-Appellees, 4
5
v. 6
7
UNITED STATES DEPARTMENT OF JUSTICE, including 8
its component the Office of Legal Counsel, UNITED 9
STATES DEPARTMENT OF DEFENSE, including its 10
component U.S. Special Operations Command, CENTRAL 11
INTELLIGENCE AGENCY, 12
13
Defendants-Appellees-Cross-Appellants. 14
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Before: NEWMAN, CABRANES, and POOLER, Circuit Judges. 16
17
Appeal and cross-appeal from the July 23, 2015, 18
judgment of the District Court for the Southern District of 19
New York (Colleen McMahon, now-Chief Judge) in a case 20
brought under the Freedom of Information Act. The judgment 21
granted in part and denied in part disclosure of documents 22
sought from the Office of Legal Counsel of the Department 23

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of Justice, the Central Intelligence Agency, and the 1
Department of Defense concerning drone strikes. 2
Affirmed on the appeal, reversed on the cross-appeal, 3
and remanded for entry of a revised judgment. 4
5
Brett Max Kaufman, New York, NY 6
(Jameel Jaffer, Hina Shamsi, 7
Matthew Spurlock, American Civil 8
Liberties Union Foundation, New 9
York, NY, Colin Wicker, Dorsey & 10
Whitney LLP, Minneapolis, MN, on 11
the brief), for Plaintiffs- 12
Appellants-Cross-Appellees. 13
14
Sarah S. Normand, Asst. U.S. Atty., 15
New York, NY (Preet Bharara, 16
U.S. Atty., New York, NY, 17
Benjamin C. Mizer, Principal 18
Deputy Asst. Atty. General, 19
Matthew M. Collette, Sharon 20
Swingle, Civil Division, U.S. 21
Dep’t of Justice, Washington, 22
DC, on the brief), for 23
Defendants-Appellees-Cross- 24
Appellants. 25
26
JON O. NEWMAN, Circuit Judge: 27
This is the third appellate round of a case brought 28
under the Freedom of Information Act (“FOIA”). The case 29
began in February 2012 to challenge responses to FOIA 30
requests made in October 2011 to the Office of Legal 31
Counsel (“OLC”) of the Department of Justice (“DOJ”), the 32
Central Intelligence Agency (“CIA”), and the Department of 33

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Defense (“DOD”). The requests were made by the American 1
Civil Liberties Union and the American Civil Liberties 2
Foundation (collectively “ACLU”). The requests were also 3
made by The New York Times and two of its reporters, but 4
they are not parties in the pending appeal. 5
ACLU appeals and DOJ cross-appeals from the July 23, 6
2015, judgment of the District Court for the Southern 7
District of New York (Colleen McMahon, now-Chief Judge). 8
That judgment ruled that OLC, CIA, and DOD were entitled to 9
withhold from disclosure a number of documents concerning 10
drone strikes -- lethal attacks by unmanned aircraft. The 11
judgment also ruled that OLC must disclose all or portions 12
of four documents 1 and CIA must disclose all or portions of 13
three documents 2 concerning such strikes. ACLU has narrowed 14
its request to 59 documents, 3 including the seven documents 15
ordered disclosed in full or in part. ACLU’s appeal 16
challenges the District Court’s ruling to the extent it 17
upheld nondisclosure of 52 documents, and the Government’s 18
1 OLC 46, 50, 144, and 145.
2 CIA 59 tab C, 109, and 113.
3 OLC 1, 2, 8, 9, 46, 50, 64, 65, 66, 70, 71, 73, 75, 76,
83, 84, 90, 91, 95, 144, and 145; CIA 2, 3, 12, 15, 33, 34, 35,
36, 45, 59 tab C, 61, 62, 78, 94, 95, 96, 105, 106, 107, 109,
110, 111, 112, 113, 117, 118, 119, 120, 123, 124, 140, and 142;
DOD 1, 31, 38, 39, 46, and 55.

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cross-appeal challenges the ruling to the extent it ordered 1
disclosure, in whole or in part, of seven documents. 2
We conclude that none of the 52 withheld documents must 3
be disclosed, and that the seven documents ordered 4
disclosed may also be withheld. We therefore affirm on the 5
appeal, reverse on the cross-appeal, and remand for entry 6
of a revised judgment. 7
Litigation history. Our first encounter with this 8
litigation concerned consolidated appeals from the January 9
24, 2013, judgment of the District Court, dismissing on 10
motion for summary judgment two consolidated suits, one 11
brought by The New York Times and two of its reporters and 12
another brought by ACLU. See New York Times Co. v. U.S. 13
Dep’t of Justice, 915 F. Supp. 2d 508 (S.D.N.Y. 2013), 14
modified by 2013 WL 238928 (S.D.N.Y. Jan. 22, 2013). On 15
those consolidated appeals, we ordered disclosure of a 16
redacted version of the “OLC-DOD Memorandum,” a 41-page 17
document, prepared by OLC, arguing the legal justification 18
for the drone strikes that killed Anwar al-Awlaki, Samir 19
Khan, and al-Awlaki’s son, Abdulrahman al-Awlaki. See New 20
York Times Co. v. U.S. Dep’t of Justice, 756 F.3d 100, 124 21
(Conclusion ¶ 1) (2d Cir. 2014) (revised opinion) (“NYTimes 22

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I”). All three victims were United States citizens, either 1
by birth or naturalization. Pertinent to the pending 2
appeal, NYTimes I also ordered: 3
• OLC to disclose some of the titles and descriptions 4
of documents listed on its Vaughn index,4 id. (Conclusion 5
¶ 2); 6
• OLC to submit various legal memoranda to the District 7
Court for “in camera inspection and determination of waiver 8
of privileges and appropriate redaction,” id. (Conclusion 9
¶ 3) (italics added); and 10
• CIA and DOD to submit Vaughn indices to the District 11
Court for “in camera inspection and determination of 12
appropriate disclosure and appropriate redaction,” id. 13
(Conclusion ¶ 5). 14
In response to the Government’s petition for rehearing 15
of NYTimes I, we made a slight revision of that opinion, 16
made slight further redactions of the OLC-DOD Memorandum, 17
and permitted the Government to withhold from disclosure 18
4 A Vaughn index is a list of documents, identified by
number, title, and description, that a Government agency
determines are responsive to an FOIA request. The index states
the one or more FOIA exemptions that the agency claims justify
withholding each document. The term derives from Vaughn v.
Rosen, 484 F.2d 820 (D.C. Cir. 1973).

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the titles and descriptions of some documents listed on the 1
OLC Vaughn index, confirming a withholding authorized by an 2
order issued May 28, 2014. See New York Times Co. v. U.S. 3
Dep’t of Justice, 756 F.3d 97, 99 (2d Cir. 2014) (first 4
opinion on Government’s petition for rehearing of NYTimes 5
I). We also bifurcated for later decision the Government’s 6
request for permission to withhold from disclosure 7
additional titles and descriptions of documents listed on 8
the OLC Vaughn index. See id. at 98-99. 9
Later, completing our ruling on the Government’s 10
petition for rehearing, we permitted the Government to 11
withhold from disclosure the titles and descriptions of 12
additional documents listed on the OLC Vaughn index and the 13
titles of other documents listed on that index. See New 14
York Times Co. v. U.S. Dep’t of Justice, 758 F.3d 436, 441 15
(2d Cir. 2014) (second opinion on Government’s petition for 16
rehearing of NYTimes I). We also ordered DOJ to make public 17
its previously classified OLC Vaughn index, as permissibly 18
redacted. See id. With the Government’s petition for 19
rehearing completely adjudicated, the District Court was 20
left with the task, as directed in NYTimes I, to consider 21
in camera whether several undisclosed OLC documents, sought 22

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in the original FOIA requests, should be disclosed. See 1
NYTimes I, 756 F.3d at 124 (Conclusion ¶ 3). 2
On remand, the District Court ruled that ten of eleven 3
OLC documents, identified in an affidavit of an OLC 4
official, could be withheld from disclosure. See No. 1:11- 5
cv-09336-CM, Dkt. No. 52 (Oct. 31, 2014). The District 6
Court rejected the Government’s request to redact three 7
paragraphs from its opinion. See id., Dkt. No. 51. The 8
Court certified its rulings for immediate appeal under Rule 9
54(b) of the Federal Rules of Civil Procedure. See id. Dkt. 10
No. 52. 11
Those rulings precipitated the second appellate round 12
of this litigation. We ruled that the ten identified 13
documents could be withheld. See New York Times Co. v. U.S. 14
Dep’t of Justice, 806 F.3d 682, 690-91 (2d Cir. 2015) 15
(“NYTimes II”). We also ruled that the District Court could 16
make public, except for a few words, the three paragraphs 17
of its opinion the Government had sought to keep 18
undisclosed. See id. Finally, we upheld the Government’s 19
request to redact a small portion of the transcript of the 20
Government’s ex parte and in camera oral argument before 21
this Court. See id. 22

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NYTimes II left for the District Court the laborious 1
task of examining the numerous OLC, CIA, and DOD documents 2
that the Government claimed were exempt from disclosure. 3
The Government had identified the OLC documents in its OLC 4
Vaughn index, which was originally classified. NYTimes I 5
ordered a redacted version of that index disclosed. 756 6
F.3d at 124 (Conclusion ¶ 2). The Government had identified 7
the CIA and DOD documents in its classified CIA and DOD 8
Vaughn indices. NYTimes I had ordered preparation of those 9
indices and their consideration by the District Court in 10
camera for determination of appropriate disclosure and 11
redaction. Id. (Conclusion ¶ 5). 12
Undertaking this task, the District Court examined the 13
documents listed on the OLC, CIA, and DOD Vaughn indices. 14
In a sealed unredacted draft opinion filed on May 13, 2015, 15
and superseded by a sealed unredacted final opinion filed 16
on June 23, 2015, 5 the District Court required disclosure of 17
redacted versions of three OLC documents, OLC 46, OLC 144, 18
5 The District Court explained in its July 17, 2015, order
concluding the litigation that the June 23, 2015, opinion
“completely superseded” the Court’s May 13, 2015, draft opinion.
The July 17, 2015, order slightly amended the June 23, 2015,
unredacted opinion and also reported that a redacted version of
the June 23, 2015, opinion had been filed “yesterday,” i.e.,
July 16, 2015. SPA 162-64.

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and OLC 145; the complete text of OLC 50; 6 the complete text 1
of Tab C to CIA 59; and redacted versions of CIA 109 and 2
CIA 113. See ACLU v. U.S. Dep’t of Justice, No. 12 Civ. 3
794(CM), 2015 WL 4470192, at *13-14, *23, *27, *39, *42-43, 4
*45 (S.D.N.Y. July 16, 2015) (redacted opinion). 5
In its redacted opinion, the District Court identified 6
six facts, Nos. 1-5 and 7, that it ruled (with one slight 7
qualification of No. 7 not material to this appeal) had 8
been officially acknowledged. See id. *4-5. The Court also 9
identified a seventh fact (No. 6), see id. at *5, for 10
consideration by this Court as to whether it had been 11
officially acknowledged, see id. at *6. The District Court 12
ruled that the six acknowledged facts must be disclosed “to 13
the extent that these specific facts appear in documents on 14
the Agencies’ Vaughn Indices and can be segregated from 15
other, properly exempt information.” Id. at *5. The Court 16
6 Both the District Court’s June 23, 2015, draft opinion and
its July 16, 2015, revised opinion identified this OLC document
as No. 50. See SPA 58, 59. However, the District Court’s July
17, 2015, order, recapitulating its rulings, see SPA 164, and
the judgment, see SPA 166, identified the document as No. 150.
The Government’s brief identified the document as No. 50. See
Br. for Government at 60-62.
We are satisfied that 50 is the correct number and that 150
is a typographical error. This is clear from the description of
the document in the District Court’s draft and revised opinion
and the fact that there is no OLC No. 150.

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stated that disclosure of these six facts is “[a]pplicable 1
to [a]ll [d]ocuments,” id. at *2, but qualified that 2
statement to make clear that the disclosure requirement 3
does not apply to any document reviewed by the Court in 4
camera, “because the [C]ourt took those facts into account 5
when reviewing the document,” id. at *15. With the 6
exception of the seven documents ordered to be disclosed, 7
the District Court ruled that all other requested documents 8
need not be disclosed. 9
With respect to the six facts, the District Court 10
ordered OLC, CIA, and DOD to make a “segregability review” 11
of each document that the Court had not reviewed in camera 12
and then represent either that the six facts had not been 13
officially acknowledged, or, if so acknowledged, that the 14
facts cannot reasonably be segregated from information 15
exempt from disclosure. See id. at *6-7. The Government 16
responded with classified declarations from OLC, CIA, and 17
DOD, which contended that segregation of all six facts 18
could not be made. [CSA 492, 516, 544] On July 16, 2015, 19
the District Court issued an order agreeing with the 20

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agencies’ contention. See No. 1:12-cv-00794-CM, Dkt. No. 1
129 (July 16, 2015). 7
2
Uncertain as to the status of three documents -- CIA 3
61, CIA 96, and DOD 1, this Court requested the Government 4
to produce them ex parte for our in camera inspection. No. 5
15-2956, Dkt. No. 166 (2d Cir. Oct. 21, 2016). We have 6
examined them. 7
The District Court’s ruling that 52 documents should be 8
withheld and that all or part of seven documents should be 9
disclosed is now fully submitted for our review. 10
Discussion 11
Although the history of this litigation is regrettably 12
complicated, disposition of the pending appeal and cross- 13
appeal is fairly straightforward. In general, continued 14
withholding of documents challenged on ACLU’s appeal and 15
reversal of the District Court’s disclosure rulings 16
challenged on the Government’s cross-appeal are warranted 17
either because disclosure would reveal information that 18
7 After an inquiry from this Court, see No. 15-2956, Dkt.
136 (2d Cir. Aug. 30, 2016), a response from the District Court,
see No. 1:12-cv-00794-CM, Dkt. No. 142 (Oct. 20, 2016), and a
further inquiry from this Court, see No. 15-2956, Dkt. No. 168
(2d Cir. Oct. 21, 2016), the District Court confirmed this
conclusion, see No. 1:12-cv-00794-CM, Dkt. No. 144 (Oct. 21,
2016).

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should remain secret or because the documents are 1
predecisional drafts protected by FOIA Exemption 5. See 2
Brennan Center for Justice v. U.S. Dep’t of Justice, 697 3
F.3d 184, 206-07 (2d Cir. 2012); Lahr v. National 4
Transportation Safety Board, 569 F.3d 964, 981-84 (9th Cir. 5
2009); Abdelfattah v. U.S. Dep’t of Homeland Security, 488 6
F.3d 178, 183-84 (3d Cir. 2007). 7
ACLU’s appeal. We appreciate the difficulty ACLU 8
encounters in challenging the District Court’s decision to 9
withhold from disclosure 52 documents. ACLU has not seen 10
either the documents or the redacted portions of the 11
District Court’s opinion explaining the Court’s reasons. 12
Having carefully considered each of these documents, we 13
conclude that each of the District Court’s withholding 14
decisions was correct. The documents are protected by one 15
or more FOIA exemptions and no waiver of secrecy has 16
occurred with respect to any of them. Our ruling does not 17
turn on the issue of so-called “working law,” an issue 18
contested by ACLU. 19
The seven facts. At oral argument, it became clear that 20
the issue as to the seven facts identified by the District 21
Court in its July 16, 2015 opinion was whether the 22

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Government was asserting the right to withhold any 1
documents because these facts were contained in them. To 2
assist in resolving that issue the District Court directed 3
the relevant agencies to make a segregability review to 4
determine if the six acknowledged facts could be segregated 5
from protected portions of the documents in which they are 6
contained. As explained above, the District Court ruled 7
that the agencies’ submissions persuasively showed that 8
segregation could not be made. We agree with that ruling. 9
No further consideration of these six facts is needed. 10
With regard to the seventh fact, which the District 11
Court left for our consideration, we conclude that it is 12
unnecessary for the resolution of this appeal to determine 13
whether it has been officially acknowledged. The Government 14
did not assert the right to withhold any of the documents 15
at issue in this appeal on the ground that those documents 16
contained the seventh fact. Accordingly, even if we were to 17
conclude that the Government publicly acknowledged the 18
seventh fact, we would not order disclosure of any document 19
on that basis. No further consideration of the seventh fact 20
is required. 21

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Government’s cross-appeal. The seven documents ordered 1
disclosed by the District Court require individual 2
consideration. 3
OLC 46: This document, ordered disclosed in redacted 4
form, is an informal memo, attempting to summarize a 5
meeting at which legal advice was discussed. Indicating the 6
preliminary nature of the memo, the agency staff member who 7
prepared it asked the recipients to correct anything that 8
the writer had tried to summarize. The document is 9
predecisional under Exemption 5 and therefore need not be 10
disclosed. 11
OLC 50: This document is a draft of two paragraphs that 12
the document preparer suggested might be included in the 13
DOJ White Paper, the document, first leaked and then 14
officially disclosed, which provided a brief legal 15
justification for drone strikes. See NYTimes I, 756 F.3d at 16
110. Ultimately, the two paragraphs were not included in 17
the White Paper. The District Court considered the two 18
paragraphs similar to the legal advice contained in the 19
White Paper and the OLC-DOD Memorandum, as to which 20
privileges had been waived by disclosure. We acknowledge 21
some similarities, but agree with the Government that the 22

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document is demonstrably a draft. ACLU previously explained 1
that it is not seeking “drafts in this litigation,” and 2
stated that “[i]f the Court determines that [the 3
description of OLC 50 as a draft is] accurate, [then it] no 4
longer seeks th[at] document.” Reply Br. for ACLU at 17 5
n.11. Accordingly, because OLC is a draft protected by 6
Exemption 5 as predecisional and no longer sought by ACLU, 7
OLC 50 need not be disclosed. 8
OLC 144: This document, ordered disclosed in part, is a 9
set of suggested talking points concerning the legal basis 10
for drone strikes. We agree with the Government that the 11
document is predecisional and need not be disclosed. 12
Government officials do not lose the protection of 13
Exemption 5 by considering informally how to present a 14
legal analysis. 15
OLC 145: This is an internal outline of classified 16
facts and some fragmentary discussion of legal advice, 17
prepared in connection with the drafting of legal advice. 18
Although the District Court properly redacted portions of 19
the document, the remainder is also entitled to remain 20
protected as predecisional under Exemption 5. The document 21
need not be disclosed. 22

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CIA 59 tab C: This is a draft of a proposed op-ed 1
article that suggested some ways of explaining the 2
Government’s legal reasoning in support of drone strikes. 3
It was never published. Although it reveals some of the 4
unnamed writer’s thinking about legal justification for 5
drone strikes, it is a draft and for that reason 6
predecisional. It need not be disclosed. 7
CIA 109 and CIA 113: These documents, which the 8
District Court disclosed in part, are informal and 9
preliminary. The second is unsigned and undated. Despite 10
the redactions, some phrases entitled to secrecy remain. 11
Although both appear to have been written after the action 12
they comment on, they are nonetheless predecisional with 13
respect to the formulation of a policy or a clear legal 14
position. Neither document need be disclosed. 15
Conclusion 16
Chief Judge McMahon ably performed the burdensome task 17
of examining scores of documents in this protracted 18
litigation, which now appears to be concluded. Despite our 19
slight disagreement with her assessment of a few of these 20
documents, we appreciate her diligence and the helpful 21
explanations in her sealed opinion. 22

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On ACLU’s appeal, the judgment is affirmed; on the 1
Government’s cross-appeal, the judgment is reversed; the 2
case is remanded for entry of a revised judgment. 3

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