      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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 1	   AMERICAN CIVIL LIBERTIES UNION, AMERICAN CIVIL
 2	   LIBERTIES UNION FOUNDATION,
 3	
 4	                   Plaintiffs-Appellants-Cross-Appellees,
 5	
 6	                           v.
 7	
 8	   UNITED STATES DEPARTMENT OF JUSTICE, including
 9	   its component the Office of Legal Counsel, UNITED
10	   STATES DEPARTMENT OF DEFENSE, including its
11	   component U.S. Special Operations Command, CENTRAL
12	   INTELLIGENCE AGENCY,
13	
14	            Defendants-Appellees-Cross-Appellants.
      - - - - - - - - - - - - - - - - - - - - - -
15	
16	   Before:         NEWMAN, CABRANES, and POOLER, Circuit Judges.
17	
18	           Appeal        and       cross-appeal              from      the   July   23,       2015,

19	   judgment of the District Court for the Southern District of

20	   New     York       (Colleen         McMahon,          now-Chief         Judge)   in    a   case

21	   brought under the Freedom of Information Act. The judgment

22	   granted in part and denied in part disclosure of documents

23	   sought from the Office of Legal Counsel of the Department


                                                           1	
      	
 1	   of   Justice,       the   Central        Intelligence      Agency,   and    the

 2	   Department of Defense concerning drone strikes.

 3	        Affirmed on the appeal, reversed on the cross-appeal,

 4	   and remanded for entry of a revised judgment.

 5	
 6	                                Brett Max Kaufman, New York, NY
 7	                                     (Jameel Jaffer, Hina Shamsi,
 8	                                     Matthew Spurlock, American Civil
 9	                                     Liberties Union Foundation, New
10	                                     York, NY, Colin Wicker, Dorsey &
11	                                     Whitney LLP, Minneapolis, MN, on
12	                                     the   brief),   for  Plaintiffs-
13	                                     Appellants-Cross-Appellees.
14	
15	                                Sarah S. Normand, Asst. U.S. Atty.,
16	                                     New York, NY (Preet Bharara,
17	                                     U.S.   Atty.,     New    York,   NY,
18	                                     Benjamin C. Mizer, Principal
19	                                     Deputy    Asst.    Atty.    General,
20	                                     Matthew    M.   Collette,     Sharon
21	                                     Swingle, Civil Division, U.S.
22	                                     Dep’t of Justice, Washington,
23	                                     DC,    on     the     brief),    for
24	                                     Defendants-Appellees-Cross-
25	                                     Appellants.
26	
27	   JON O. NEWMAN, Circuit Judge:

28	        This is the third appellate round of a case brought

29	   under the Freedom of Information Act (“FOIA”). The case

30	   began   in   February      2012     to     challenge    responses     to   FOIA

31	   requests     made    in   October        2011   to   the   Office    of    Legal

32	   Counsel (“OLC”) of the Department of Justice (“DOJ”), the

33	   Central Intelligence Agency (“CIA”), and the Department of


                                                2	
      	
 1	   Defense (“DOD”). The requests were made by the American

 2	   Civil                   Liberties                             Union        and    the   American     Civil    Liberties

 3	   Foundation (collectively “ACLU”). The requests were also

 4	   made by The New York Times and two of its reporters, but

 5	   they are not parties in the pending appeal.

 6	                   ACLU appeals and DOJ cross-appeals from the July 23,

 7	   2015,                   judgment                          of         the    District     Court   for    the     Southern

 8	   District of New York (Colleen McMahon, now-Chief Judge).

 9	   That judgment ruled that OLC, CIA, and DOD were entitled to

10	   withhold from disclosure a number of documents concerning

11	   drone strikes -- lethal attacks by unmanned aircraft. The

12	   judgment also ruled that OLC must disclose all or portions

13	   of four documents1 and CIA must disclose all or portions of

14	   three documents2 concerning such strikes. ACLU has narrowed

15	   its request to 59 documents,3 including the seven documents

16	   ordered                         disclosed                            in    full    or   in   part.     ACLU’s     appeal

17	   challenges the District Court’s ruling to the extent it

18	   upheld nondisclosure of 52 documents, and the Government’s

      																																																																		
      	
                      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.

                                                                                        3	
      	
 1	   cross-appeal challenges the ruling to the extent it ordered

 2	   disclosure, in whole or in part, of seven documents.

 3	        We conclude that none of the 52 withheld documents must

 4	   be   disclosed,      and    that    the          seven     documents   ordered

 5	   disclosed may also be withheld. We therefore affirm on the

 6	   appeal, reverse on the cross-appeal, and remand for entry

 7	   of a revised judgment.

 8	        Litigation    history.        Our     first     encounter     with    this

 9	   litigation concerned consolidated appeals from the January

10	   24, 2013, judgment of the District Court, dismissing on

11	   motion   for   summary     judgment        two    consolidated    suits,   one

12	   brought by The New York Times and two of its reporters and

13	   another brought by ACLU. See New York Times Co. v. U.S.

14	   Dep’t of Justice, 915 F. Supp. 2d 508 (S.D.N.Y. 2013),

15	   modified by 2013 WL 238928 (S.D.N.Y. Jan. 22, 2013). On

16	   those    consolidated      appeals,      we      ordered    disclosure    of   a

17	   redacted   version    of    the    “OLC-DOD        Memorandum,”    a   41-page

18	   document, prepared by OLC, arguing the legal justification

19	   for the drone strikes that killed Anwar al-Awlaki, Samir

20	   Khan, and al-Awlaki’s son, Abdulrahman al-Awlaki. See New

21	   York Times Co. v. U.S. Dep’t of Justice, 756 F.3d 100, 124

22	   (Conclusion ¶ 1) (2d Cir. 2014) (revised opinion) (“NYTimes


                                            4	
      	
 1	   I”). All three victims were United States citizens, either

 2	   by            birth                    or             naturalization.            Pertinent   to   the   pending

 3	   appeal, NYTimes I also ordered:

 4	                   • OLC to disclose some of the titles and descriptions

 5	   of documents listed on its Vaughn index,4 id. (Conclusion

 6	   ¶ 2);

 7	                   • OLC to submit various legal memoranda to the District

 8	   Court for “in camera inspection and determination of waiver

 9	   of privileges and appropriate redaction,” id. (Conclusion

10	   ¶	3) (italics added); and

11	                   • CIA and DOD to submit Vaughn indices to the District

12	   Court                    for               “in               camera   inspection      and    determination   of

13	   appropriate                                   disclosure              and    appropriate     redaction,”     id.

14	   (Conclusion ¶ 5).

15	                   In response to the Government’s petition for rehearing

16	   of NYTimes I, we made a slight revision of that opinion,

17	   made slight further redactions of the OLC-DOD Memorandum,

18	   and permitted the Government to withhold from disclosure


      																																																																		
      	
                      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).

                                                                                  5	
      	
 1	   the titles and descriptions of some documents listed on the

 2	   OLC Vaughn index, confirming a withholding authorized by an

 3	   order issued May 28, 2014. See New York Times Co. v. U.S.

 4	   Dep’t of Justice, 756 F.3d 97, 99 (2d Cir. 2014) (first

 5	   opinion on Government’s petition for rehearing of NYTimes

 6	   I). We also bifurcated for later decision the Government’s

 7	   request     for    permission      to        withhold        from    disclosure

 8	   additional titles and descriptions of documents listed on

 9	   the OLC Vaughn index. See id. at 98-99.

10	        Later,       completing     our        ruling    on    the     Government’s

11	   petition    for    rehearing,    we     permitted          the    Government    to

12	   withhold    from   disclosure     the        titles   and    descriptions       of

13	   additional documents listed on the OLC Vaughn index and the

14	   titles of other documents listed on that index. See New

15	   York Times Co. v. U.S. Dep’t of Justice, 758 F.3d 436, 441

16	   (2d Cir. 2014) (second opinion on Government’s petition for

17	   rehearing of NYTimes I). We also ordered DOJ to make public

18	   its previously classified OLC Vaughn index, as permissibly

19	   redacted.    See    id.   With    the        Government’s         petition     for

20	   rehearing completely adjudicated, the                   District Court was

21	   left with the task, as directed in NYTimes I, to consider

22	   in camera whether several undisclosed OLC documents, sought


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 1	   in the original FOIA requests, should be disclosed. See

 2	   NYTimes I, 756 F.3d at 124 (Conclusion ¶ 3).

 3	         On remand, the District Court ruled that ten of eleven

 4	   OLC     documents,      identified           in     an   affidavit       of    an     OLC

 5	   official, could be withheld from disclosure. See No. 1:11-

 6	   cv-09336-CM,     Dkt.      No.    52    (Oct.        31,    2014).     The    District

 7	   Court    rejected    the    Government’s             request      to   redact       three

 8	   paragraphs from its opinion.                      See id., Dkt. No. 51. The

 9	   Court certified its rulings for immediate appeal under Rule

10	   54(b) of the Federal Rules of Civil Procedure. See id. Dkt.

11	   No. 52.

12	         Those rulings precipitated the second appellate round

13	   of    this    litigation.        We    ruled         that   the    ten     identified

14	   documents could be withheld. See New York Times Co. v. U.S.

15	   Dep’t    of   Justice,     806        F.3d        682,   690-91    (2d     Cir.     2015)

16	   (“NYTimes II”). We also ruled that the District Court could

17	   make public, except for a few words, the three paragraphs

18	   of    its     opinion      the    Government             had      sought      to     keep

19	   undisclosed. See id. Finally, we upheld the Government’s

20	   request to redact a small portion of the transcript of the

21	   Government’s ex parte and in camera oral argument before

22	   this Court. See id.


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 1	                       NYTimes II left for the District Court the laborious

 2	   task of examining the numerous OLC, CIA, and DOD documents

 3	   that the Government claimed were exempt from disclosure.

 4	   The Government had identified the OLC documents in its OLC

 5	   Vaughn index, which was originally classified. NYTimes I

 6	   ordered a redacted version of that index disclosed. 756

 7	   F.3d at 124 (Conclusion ¶ 2). The Government had identified

 8	   the CIA and DOD documents in its classified CIA and DOD

 9	   Vaughn indices. NYTimes I had ordered preparation of those

10	   indices and their consideration by the District Court in

11	   camera                      for              determination           of    appropriate   disclosure   and

12	   redaction. Id. (Conclusion ¶ 5).

13	                   Undertaking this task, the District Court examined the

14	   documents listed on the OLC, CIA, and DOD Vaughn indices.

15	   In a sealed unredacted draft opinion filed on May 13, 2015,

16	   and superseded by a sealed unredacted final opinion filed

17	   on June 23, 2015,5 the District Court required disclosure of

18	   redacted versions of three OLC documents, OLC 46, OLC 144,

      																																																																		
      	
                      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.

                                                                            8	
      	
 1	   and OLC 145; the complete text of OLC 50;6 the complete text

 2	   of Tab C to CIA 59; and redacted versions of CIA 109 and

 3	   CIA 113. See ACLU v. U.S. Dep’t of Justice, No. 12 Civ.

 4	   794(CM), 2015 WL 4470192, at *13-14, *23, *27, *39, *42-43,

 5	   *45 (S.D.N.Y. July 16, 2015) (redacted opinion).

 6	                   In its redacted opinion, the District Court identified

 7	   six facts, Nos. 1-5 and 7, that it ruled (with one slight

 8	   qualification of No. 7 not material to this appeal) had

 9	   been officially acknowledged. See id. *4-5. The Court also

10	   identified                               a        seventh               fact   (No.        6),   see   id.    at    *5,    for

11	   consideration                                       by           this    Court        as   to    whether     it    had    been

12	   officially acknowledged, see id. at *6. The District Court

13	   ruled that the six acknowledged facts must be disclosed “to

14	   the extent that these specific facts appear in documents on

15	   the Agencies’ Vaughn Indices and can be segregated from

16	   other, properly exempt information.” Id. at *5. The Court

      																																																																		
      	
                      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.

                                                                                       9	
      	
 1	   stated that disclosure of these six facts is “[a]pplicable

 2	   to    [a]ll     [d]ocuments,”      id.           at    *2,    but    qualified      that

 3	   statement     to   make    clear      that        the    disclosure        requirement

 4	   does not apply to any document reviewed by the Court in

 5	   camera, “because the [C]ourt took those facts into account

 6	   when    reviewing       the     document,”            id.     at    *15.    With     the

 7	   exception of the seven documents ordered to be disclosed,

 8	   the District Court ruled that all other requested documents

 9	   need not be disclosed.

10	          With   respect     to    the    six        facts,      the    District      Court

11	   ordered OLC, CIA, and DOD to make a “segregability review”

12	   of each document that the Court had not reviewed in camera

13	   and then represent either that the six facts had not been

14	   officially acknowledged, or, if so acknowledged, that the

15	   facts    cannot    reasonably         be         segregated        from    information

16	   exempt from disclosure. See id. at *6-7. The Government

17	   responded with classified declarations from OLC, CIA, and

18	   DOD,    which    contended      that    segregation            of    all    six    facts

19	   could not be made.             [CSA 492, 516, 544] On July 16, 2015,

20	   the    District    Court       issued       an        order   agreeing       with    the




                                                 10	
      	
 1	   agencies’ contention. See No. 1:12-cv-00794-CM, Dkt. No.

 2	   129 (July 16, 2015).7

 3	                   Uncertain as to the status of three documents -- CIA

 4	   61, CIA 96, and DOD 1, this Court requested the Government

 5	   to produce them ex parte for our in camera inspection. No.

 6	   15-2956, Dkt. No. 166 (2d Cir. Oct. 21, 2016). We have

 7	   examined them.

 8	                   The District Court’s ruling that 52 documents should be

 9	   withheld and that all or part of seven documents should be

10	   disclosed is now fully submitted for our review.

11	                                                                             Discussion

12	                   Although the history of this litigation is regrettably

13	   complicated, disposition of the pending appeal and cross-

14	   appeal                     is            fairly                      straightforward.        In   general,     continued

15	   withholding of documents challenged on ACLU’s appeal and

16	   reversal                            of              the               District         Court’s    disclosure     rulings

17	   challenged on the Government’s cross-appeal are warranted

18	   either                     because                        disclosure         would         reveal   information    that

      																																																																		
      	
                      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).

                                                                                       11	
      	
 1	   should      remain        secret        or     because        the        documents     are

 2	   predecisional           drafts    protected         by     FOIA    Exemption     5.    See

 3	   Brennan Center for Justice v. U.S. Dep’t of Justice, 697

 4	   F.3d     184,      206-07        (2d       Cir.     2012);        Lahr     v.   National

 5	   Transportation Safety Board, 569 F.3d 964, 981-84 (9th Cir.

 6	   2009); Abdelfattah v. U.S. Dep’t of Homeland Security, 488

 7	   F.3d 178, 183-84 (3d Cir. 2007).                    	

 8	          ACLU’s      appeal.       We        appreciate       the     difficulty        ACLU

 9	   encounters in challenging the District Court’s decision to

10	   withhold from disclosure 52 documents. ACLU has not seen

11	   either      the    documents          or     the    redacted        portions    of    the

12	   District Court’s opinion explaining the Court’s reasons.

13	          Having carefully considered each of these documents, we

14	   conclude      that       each    of    the     District       Court’s       withholding

15	   decisions was correct. The documents are protected by one

16	   or   more     FOIA      exemptions          and     no    waiver     of    secrecy    has

17	   occurred with respect to any of them. Our ruling does not

18	   turn on the issue of so-called “working law,” an issue

19	   contested by ACLU.

20	          The seven facts. At oral argument, it became clear that

21	   the issue as to the seven facts identified by the District

22	   Court    in       its    July     16,       2015        opinion    was     whether     the


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 1	   Government      was     asserting    the    right     to   withhold    any

 2	   documents because these facts were contained in them. To

 3	   assist in resolving that issue the District Court directed

 4	   the relevant agencies to make a segregability review to

 5	   determine if the six acknowledged facts could be segregated

 6	   from protected portions of the documents in which they are

 7	   contained.     As     explained   above,   the   District   Court     ruled

 8	   that    the   agencies’     submissions     persuasively    showed    that

 9	   segregation could not be made. We agree with that ruling.

10	   No further consideration of these six facts is needed.

11	          With regard to the seventh fact, which the District

12	   Court left for our consideration, we conclude that it is

13	   unnecessary for the resolution of this appeal to determine

14	   whether it has been officially acknowledged. The Government

15	   did not assert the right to withhold any of the documents

16	   at issue in this appeal on the ground that those documents

17	   contained the seventh fact. Accordingly, even if we were to

18	   conclude      that    the   Government     publicly   acknowledged     the

19	   seventh fact, we would not order disclosure of any document

20	   on that basis. No further consideration of the seventh fact

21	   is required.




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 1	         Government’s cross-appeal. The seven documents ordered

 2	   disclosed        by     the     District         Court    require        individual

 3	   consideration.

 4	         OLC 46: This document, ordered disclosed in redacted

 5	   form,    is   an      informal       memo,       attempting    to    summarize     a

 6	   meeting at which legal advice was discussed. Indicating the

 7	   preliminary nature of the memo, the agency staff member who

 8	   prepared it asked the recipients to correct anything that

 9	   the     writer     had      tried     to     summarize.       The   document       is

10	   predecisional under Exemption 5 and therefore need not be

11	   disclosed.

12	         OLC 50: This document is a draft of two paragraphs that

13	   the document preparer suggested might be included in the

14	   DOJ   White      Paper,       the    document,      first     leaked      and    then

15	   officially        disclosed,         which        provided     a    brief       legal

16	   justification for drone strikes. See NYTimes I, 756 F.3d at

17	   110. Ultimately, the two paragraphs were not included in

18	   the   White      Paper.     The     District      Court   considered       the   two

19	   paragraphs similar to the legal advice contained in the

20	   White    Paper        and     the   OLC-DOD       Memorandum,       as   to     which

21	   privileges had been waived by disclosure. We acknowledge

22	   some similarities, but agree with the Government that the


                                                 14	
      	
 1	   document is demonstrably a draft. ACLU previously explained

 2	   that it is not seeking “drafts in this litigation,” and

 3	   stated     that        “[i]f     the     Court            determines         that     [the

 4	   description of OLC 50 as a draft is] accurate, [then it] no

 5	   longer seeks th[at] document.” Reply Br. for ACLU at 17

 6	   n.11.    Accordingly,          because   OLC         is     a   draft    protected      by

 7	   Exemption 5 as predecisional and no longer sought by ACLU,

 8	   OLC 50 need not be disclosed.

 9	         OLC 144: This document, ordered disclosed in part, is a

10	   set of suggested talking points concerning the legal basis

11	   for drone strikes. We agree with the Government that the

12	   document       is    predecisional        and        need       not     be   disclosed.

13	   Government          officials     do     not         lose       the     protection      of

14	   Exemption      5     by   considering      informally            how    to   present    a

15	   legal analysis.

16	         OLC 145: This is an internal outline of classified

17	   facts    and    some      fragmentary       discussion            of    legal     advice,

18	   prepared in connection with the drafting of legal advice.

19	   Although the District Court properly redacted portions of

20	   the   document,        the   remainder          is    also      entitled     to     remain

21	   protected as predecisional under Exemption 5. The document

22	   need not be disclosed.


                                                15	
      	
 1	        CIA 59 tab C: This is a draft of a proposed op-ed

 2	   article     that     suggested         some        ways        of     explaining      the

 3	   Government’s legal reasoning in support of drone strikes.

 4	   It was never published. Although it reveals some of the

 5	   unnamed    writer’s      thinking          about     legal          justification     for

 6	   drone     strikes,     it     is       a     draft       and        for     that   reason

 7	   predecisional. It need not be disclosed.

 8	        CIA    109    and      CIA    113:          These    documents,          which   the

 9	   District     Court       disclosed          in     part,       are         informal   and

10	   preliminary. The second is unsigned and undated. Despite

11	   the redactions, some phrases entitled to secrecy remain.

12	   Although both appear to have been written after the action

13	   they comment on, they are nonetheless predecisional with

14	   respect to the formulation of a policy or a clear legal

15	   position. Neither document need be disclosed.

16	                                      Conclusion

17	        Chief Judge McMahon ably performed the burdensome task

18	   of   examining       scores       of       documents       in        this     protracted

19	   litigation, which now appears to be concluded. Despite our

20	   slight disagreement with her assessment of a few of these

21	   documents,    we     appreciate            her    diligence          and    the    helpful

22	   explanations in her sealed opinion.


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1	       On   ACLU’s   appeal,   the   judgment   is   affirmed;   on   the

2	   Government’s cross-appeal, the judgment           is reversed; the

3	   case is remanded for entry of a revised judgment.




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