          United States Court of Appeals
                     For the First Circuit

No. 13-1994

                       LEITICIA CASTAÑEDA,

                      Petitioner, Appellee,

                               v.

STEVE SOUZA, Superintendent, Bristol County House of Corrections,
     in his official capacity and his successors and assigns,

                     Respondent, Appellant,

 BRUCE E. CHADBOURNE, Field Office Director, Boston Field Office,
   Office of Detention and Removal, U.S. Immigrations and Customs
      Enforcement, U.S. Department of Homeland Security, in his
official capacity and his successors and assigns; JOHN T. MORTON,
       Director, U.S. Immigration and Customs Enforcement, U.S.
Department of Homeland Security, in his official capacity and his
  successors and assigns; JEH JOHNSON, Secretary, U.S. Department
of Homeland Security, in his official capacity and his successors
       and assigns; ERIC H. HOLDER, JR., Attorney General, U.S.
        Department of Justice, in his official capacity and his
                        successors and assigns,

                          Respondents.


          APPEAL FROM THE UNITED STATES DISTRICT COURT
                FOR THE DISTRICT OF MASSACHUSETTS
          [Hon. William G. Young, U.S. District Judge]


No. 13-2509

          CLAYTON RICHARD GORDON, on behalf of himself
                  and others similarly situated,

                      Petitioner, Appellee,

          PRECIOSA ANTUNES; GUSTAVO RIBEIRO FERREIRA;
              VALBOURN SAHIDD LAWES; NHAN PHUNG VU,

                          Petitioners,
                                v.

     ERIC H. HOLDER, JR., United States Attorney General; JOHN
   SANDWEG, Acting Director; SEAN GALLAGHER, Acting Field Office
  Director; CHRISTOPHER J. DONELAN; MICHAEL G. BELOTTI, Sheriff;
 STEVEN W. TOMPKINS, Sheriff; THOMAS M. HODGSON, Sheriff; JOSEPH
    D. MCDONALD, JR., Sheriff; RAND BEERS, Acting Secretary of
                         Homeland Security,

                     Respondents, Appellants.


           APPEAL FROM THE UNITED STATES DISTRICT COURT
                 FOR THE DISTRICT OF MASSACHUSETTS
          [Hon. Michael A. Ponsor, U.S. District Judge]


                              Before
                  Torruella, Dyk,* and Thompson,
                         Circuit Judges.



     Elianis N. Pérez, Senior Litigation Counsel, United States
Department of Justice, Civil Division, Office of Immigration
Litigation, with whom Sarah B. Fabian, Trial Attorney, District
Court Section, Stuart F. Delery, Assistant Attorney General, Civil
Division, Colin A. Kisor, Director, Office of Immigration
Litigation, and Elizabeth J. Stevens, Assistant Director, were on
brief, for respondents-appellants Steve Souza, Eric H. Holder, Jr.,
John Sandweg, Sean Gallagher, Christopher J. Donelan, Michael G.
Bellotti, Steven W. Tompkins, Thomas M. Hodgson, Joseph D.
McDonald, Jr., and Jeh C. Johnson.
     Gregory Romanovsky, with whom Livia Lungulescu and Romanovsky
Law Offices were on brief, for appellee Castañeda.
     Matthew R. Segal, with whom Adriana Lafaille, American Civil
Liberties Union of Massachusetts, Judy Rabinovitz, Eunice Lee,
Michael Tan, ACLU Foundation Immigrants’ Rights Project, Elizabeth
Badger, and Lutheran Social Services were on brief, for appellee
Gordon.
     Alina Das, Sean McMahon, Legal Intern, Etan Newman, Legal
Intern, and Washington Square Legal Services, Inc., Immigrant
Rights Clinic, on brief for Detention Watch Network, Families for
Freedom, Greater Boston Legal Services, Harvard Immigration and
Refugee Clinical Program, Immigrant Defense Project, Immigrant
Rights Clinic, Maine People’s Alliance, National Immigrant Justice

     *
      Of the Federal Circuit, sitting by designation.
                               -2-
Center, Political Asylum/Immigration Representation (PAIR) Project,
University of Maine School of Law Immigrant and Refugee Rights
Clinic, as amici curiae in support of petitioners-appellees
Castañeda & Gordon.
     Prasant D. Desai and Iandoli & Desai, P.C., on brief for
American Civil Liberties Union Foundation, American Civil Liberties
Union Foundation of Massachusetts, American Immigration Lawyers
Association, and the National Immigration Project of the National
Lawyers Guild, as amici curiae in support of petitioner-appellee
Castañeda.


                         October 6, 2014
             DYK, Circuit Judge.        In these consolidated habeas cases,

we must determine whether the petitioners, two aliens, are subject

to    the   mandatory   detention       provision   of    the   Immigration       and

Nationality Act, 8 U.S.C. § 1226(c).             Subsection 1226(c) provides

that the Attorney General “shall take into custody any alien,” who

has    committed   certain   predicate         crimes,    “when    the   alien     is

released.”     Unlike other aliens facing the possibility of removal

from the United States, aliens subject to mandatory detention are

generally ineligible for bail even if they show to the Attorney

General’s satisfaction that they are not dangerous and are likely

to appear at removal hearings.

             Each of the petitioners here committed a predicate crime

listed in § 1226(c)1 but was not taken into custody by the Attorney

General until years after being released from state custody.

Because § 1226(c) only applies to aliens detained “when . . .

released” from criminal custody, and because the petitioners were

not timely detained under any reasonable interpretation of the

statute, we conclude that the petitioners are not subject to

mandatory     detention   under     §    1226(c)    and   are     entitled   to   an

individualized bail hearing under § 1226(a).               We therefore affirm

the district court’s grant of habeas corpus relief in each case.



       1
          Predicate crimes under § 1226(c) cover a variety of
offenses. Of note in this case, non-violent drug possession is a
predicate act. See 8 U.S.C. §§ 1226(c)(1)(B), 1227(A)(2)(B)(i).


                                         -4-
                                   I.

                                   A.

            The   mandatory   detention    provision   of   section   1226,

subsection (c), is part of a section of the Immigration and

Nationality Act which governs the arrest and detention of aliens

subject to removal from the United States.       See generally 8 U.S.C.

§ 1226.     The general rule under that section is that aliens

arrested and charged with removal may be released on bond pending

removal proceedings:

     (a) Arrest, detention, and release

       On a warrant issued by the Attorney General, an alien
     may be arrested and detained pending a decision on
     whether the alien is to be removed from the United
     States.   Except as provided in subsection (c) [the
     mandatory detention provision] of this section and
     pending such decision, the Attorney General—

          (1) may continue to detain the arrested alien; and

          (2) may release the alien on—

             (A) bond of at least $1,500 . . . ; or

             (B) conditional parole . . . .

Id. § 1226(a) (emphasis added).          The statute thus provides that

after an alien’s arrest the Attorney General “may continue to

detain the arrested alien” or “may release the alien” on bond or

parole.    Id. § 1226(a)(1), (2).2         We refer to this provision,


     2
        Although   the   Attorney  General   now  shares   these
responsibilities with the Secretary of Homeland Security (see
Homeland Security Act of 2002, Pub. L. No. 107-296, §§ 402, 441,


                                   -5-
subsection (a), as the general detention provision.                      The general

detention provision does not require the Attorney General to

release an alien under any particular circumstances, nor does it

limit the factors that the Attorney General may consider in

deciding whether to detain or release an alien.                 See id.

              The process by which the Attorney General determines

whether an alien will be released on bond pursuant to subsection

(a) is governed by administrative regulations.                     See generally 8

C.F.R. § 1236.1.           The first step in the process is a bond

determination by an immigration enforcement officer.                        See id.

§ 1236.1(c)(8).          To be released, an alien must prove “to the

satisfaction of the officer” that his release would not endanger

other persons or property and that he is likely to appear for any

future proceedings.        Id.    Release may be revoked (if it is granted

at    all)   “at   any   time    in   the   discretion    of”      the   immigration

enforcement officer.        Id. § 1236.1(c)(9).

              An alien dissatisfied with his initial bond determination

may    request     a   redetermination      of   bond    by   an    administrative

immigration judge.         Id. § 1236.1(d)(1).           The immigration judge

applies the same standard as the enforcement officials and reaches

an independent judgment about the alien’s eligibility for release.

See id.      If the alien is still dissatisfied with his bond decision,


116 Stat. 2135 (Nov. 25, 2002)), for convenience, we will refer to
this authority as residing in the Attorney General and his assigns.


                                        -6-
he may take a further appeal to the Board of Immigration Appeals

(BIA).   Id. § 1236.1(d)(3).

           No judicial review is available for an alien’s bond

determination.   The statute provides:

     The Attorney General’s discretionary judgment regarding
     the application of this section shall not be subject to
     review. No court may set aside any action or decision by
     the Attorney General under this section regarding the
     detention or release of any alien or the grant,
     revocation, or denial of bond or parole.

8 U.S.C. § 1226(e).    Thus, the exclusive authority to make and

review bond determinations lies with the executive branch, whose

discretionary decisions are generally immune from review in Article

III courts.

                                B.

           The mandatory detention provision, § 1226(c), is framed

as an exception to § 1226(a)’s general detention provision.     See

id. § 1226(a) (“Except as provided in subsection (c) . . . .”).

Under this exception, aliens who have committed one or more

predicate crimes are to be detained by the Attorney General

“when . . . released” from criminal custody, and may not be

released on bond except in rare circumstances not present here.3



     3
          An alien may be released if the Attorney General
concludes that his release is necessary for witness protection
purposes related to a major criminal prosecution or investigation.
8 U.S.C. § 1226(c)(2). The alien must also demonstrate that he is
not dangerous or a flight risk, as he would under general
detention. Id.


                                -7-
The sole procedural safeguard for such aliens is a “Joseph” hearing

at which the alien “may avoid mandatory detention by demonstrating

that he is not an alien, was not convicted of the predicate crime,

or that the INS [now ICE] is otherwise substantially unlikely to

establish that he is in fact subject to mandatory detention.”

Demore v. Kim, 538 U.S. 510, 514 n.3 (2003); see also 8 C.F.R.

§ 3.19(h)(2)(ii); In re Joseph, 22 I. & N. Dec. 799 (BIA 1999).

             The predicate crimes for mandatory detention include

aggravated felonies, crimes of moral turpitude, human trafficking,

certain    firearm   offenses,   treason,   espionage,   terrorism,   and

various others.      See id. § 1226(c)(1)(A)-(D).   Of relevance here,

they also include violations of state, federal, or foreign laws

relating to controlled substances, from drug trafficking to simple

possession.     See id. §§ 1226(c)(1)(A), 1182(a)(2).     As this court

held in Saysana v. Gillen, 590 F.3d 7, 15-17 (1st Cir. 2009),

mandatory detention is limited to situations in which the alien is

released from custody related to one of the predicate crimes.

             The relevant text of subsection (c) reads as follows:

     (c) Detention of criminal aliens

          (1) Custody

           The Attorney General shall take into custody any alien
          who—

              (A) is inadmissible by reason of having committed
           any offense covered in section 1182(a)(2) of this
           title,



                                   -8-
               (B) is deportable by reason of having committed any
            offense   covered   in   section    1227(a)(2)(A)(ii),
            (A)(iii), (B), (C), or (D) of this title,

               (C) is deportable under section 1227(a)(2)(A)(i) of
            this title on the basis of an offense for which the
            alien has been sentence[d] to a term of imprisonment
            of at least 1 year, or

               (D) is inadmissible under section 1182(a)(3)(B) of
            this title or deportable under section 1227(a)(4)(B)
            of this title,

           when the alien is released, without regard to whether
           the alien is released on parole, supervised release, or
           probation, and without regard to whether the alien may
           be arrested or imprisoned again for the same offense.

       (2) Release

         The Attorney General may release an alien described in
       paragraph (1) only if the Attorney General decides
       pursuant to [18 U.S.C. § 3521] that release of the alien
       from custody is necessary [for witness protection in a
       major criminal case], and the alien satisfies the
       Attorney General that the alien will not pose a danger to
       the safety of other persons or of property and is likely
       to appear for any scheduled proceeding.       A decision
       relating to such release shall take place in accordance
       with a procedure that considers the severity of the
       offense committed by the alien.

8 U.S.C. § 1226(c) (emphasis added). Thus, the effect of § 1226(c)

is to deny individualized bond hearings during which the Attorney

General has the discretion to determine whether to detain the

individual.      The central issue in this case relates to the phrase

“when the alien is released.”

                                     C.

              In Demore v. Kim, 538 U.S. 510, the Supreme Court held

that   §    1226(c)’s   mandatory   detention   scheme   is   not   facially


                                     -9-
unconstitutional.         The alien in Demore had been detained the day

after his release from state custody. Kim v. Ziglar, 276 F.3d 523,

526 (9th Cir. 2002). He argued that § 1226(c) violates due process

because    it    allows    the   Attorney     General   to   detain   an   alien

indefinitely without a finding that the alien is dangerous or a

flight risk.      Demore, 538 U.S. at 514.       The Supreme Court rejected

that argument, concluding that aliens falling under § 1226(c) may

constitutionally be detained “for the brief period necessary for

their removal proceedings.”         Id. at 513.     The Court distinguished

an earlier case, Zadvydas v. Davis, 533 U.S. 678 (2001), which held

that aliens whose deportation is unfeasible (e.g., because no

country will accept them) cannot be held indefinitely unless the

government demonstrates a continued need for their detention.

Demore, 538 U.S. at 528.         “While the period of detention at issue

in Zadvydas [after the statutory deadline for an alien’s removal

has passed] was ‘indefinite’ and ‘potentially permanent,’ the

detention [under § 1226(c)] is of a much shorter duration.”                 Id.

(citation omitted). Statistics cited by the Court showed that most

removal cases were completed in a few months and the remainder, on

average, were completed in just four months more.              Id. at 529.

               While the Court’s opinion in Demore did not articulate

limits    on    the   permissibility    of    mandatory   detention,   Justice

Kennedy in joining the majority opinion made clear that in his view

§ 1226(c) should be construed in light of constitutional concerns


                                       -10-
if   an   alien’s   detention     became      unreasonable        or    unjustified.

Demore, 538 U.S. at 532 (Kennedy, J., concurring).                     Since Justice

Kennedy’s    vote   was    necessary    to     the    majority,        his   limiting

rationale is binding on us.4

            Justice Kennedy began his concurrence by noting that,

since mandatory detention under § 1226(c) is “premised upon the

alien’s    deportability,”       due   process       requires     “individualized

procedures” such as a Joseph hearing to ensure that the alien is in

fact deportable.      Id. At 531-32 (Kennedy, J., concurring).                    “For

similar reasons,” he continued, “since the Due Process Clause

prohibits arbitrary deprivations of liberty, a lawful permanent

resident    alien   such    as   respondent        could    be    entitled     to    an

individualized      determination      as     to   his     risk   of     flight     and

dangerousness if the continued detention became unreasonable or

unjustified.” Id. at 532. “Were there to be an unreasonable delay

by [ICE] in pursuing and completing deportation proceedings, it

could become necessary then to inquire whether the detention is not

to facilitate deportation, or to protect against risk of flight or



      4
          See Bruno & Stillman, Inc. v. Globe Newspaper Co., 633
F.2d 583, 594-95 (1st Cir. 1980) (construing the Supreme Court’s 5-
4 decision in Branzburg v. Hayes, 408 U.S. 665 (1972), to be
limited by the concurring opinion of Justice Powell); accord, e.g.,
United States v. Smith, 135 F.3d 963, 968-69 (5th Cir. 1998); see
also United States v. District of Columbia, 654 F.2d 802, 806-07
(D.C. Cir. 1981) (giving similar treatment to National League of
Cities v. Usery, 426 U.S. 833 (1976), in light of Justice
Blackmun’s necessary concurrence).


                                       -11-
dangerousness, but to incarcerate for other reasons.”                      Id. at 532-

33 (emphasis added).

           Justice Kennedy’s concurrence thus suggests that an

“unreasonable   delay   by       [ICE]    in    pursuing      .    .   .   deportation

proceedings” could make mandatory detention under subsection (c)

constitutionally suspect and requires a limiting construction.                      We

must determine here whether the government’s years-long delay means

that the petitioners are entitled to an individualized bond hearing

under § 1226(a), or if they are subject to mandatory detention

under § 1226(c).

                                         II.

                                          A.

           Leiticia Castaneda is a native and citizen of Brazil.

Castaneda entered the United States without inspection (illegally,

that is) in 2000.     Castaneda was seventeen years old at the time.

In 2008, Castaneda was arrested for possession of cocaine, a

misdemeanor   under   Massachusetts            law    and   listed     predicate   for

mandatory detention under § 1226(c).                 See Mass. Gen. Laws Ch. 94C,

§ 34; 8 U.S.C. §§ 1226(c)(1)(A), 1182(a)(2)(A)(i)(II) (listing as

a predicate for mandatory detention “a[ny] violation of . . . any

law   or   regulation        .     .     .      relating      to       a    controlled

substance . . . .”).    It is unclear whether Castaneda remained in

police custody or pretrial detention after her arrest.                      On October

6, 2008, Castaneda was convicted and released on probation, from


                                         -12-
which she was discharged in February 2010.                       Since her release,

according to the Detention Watch Network Amici Br. at 16-18,

Castaneda has begun living with her son, has been working as a

night cleaner, has cooperated with police in an effort to prosecute

a man who had abused her, and has applied for a U Visa (a type of

visa set aside for victims of certain crimes).

                In March 2013, four and a half years after her conviction

and release in 2008, Castaneda was arrested, detained, and charged

with removal by ICE agents.5                The stated ground for removal was

Castaneda’s             inadmissibility     due    to    her    cocaine    possession

conviction.             Castaneda appears not to have disputed her criminal

status or removability. She did, however, seek release on bond for

the duration of her removal proceedings under § 1226(a).                             An

immigration judge denied her request for release, finding that she

was subject to mandatory detention under § 1226(c).

                Castaneda then filed a petition for writ of habeas corpus

in the District of Massachusetts.                       The petition alleged that

Castaneda’s detention without opportunity for release on bond was

unauthorized              by   law    because       she        was   not     detained

“when       .   .   .    released”   from   criminal      custody    as   required   by



        5
          The statute provides that Castaneda’s period of probation
is not to be considered in determining her date of release.
§ 1226(c)(1) (“. . . when the alien is released, without regard to
whether the alien is released on parole, supervised release, or
probation . . . .”).


                                            -13-
§ 1226(c). The petition requested that the district court order an

individualized bond hearing and bond redetermination before an

immigration judge.

            After a hearing, the district court granted Castaneda’s

petition and issued a writ of habeas corpus ordering the government

to release Castaneda unless it provided her a bond hearing within

ten days.    The court reasoned that the most natural reading of

“when released” was “immediately upon release,” and therefore, in

light of the statutory context, statutory structure, the rule of

lenity, and the absence of congressional intent to the contrary,

section 1226(c) applies only to criminal aliens who have been

detained immediately upon release from criminal custody or within

a reasonable time thereafter.      A few days later, prior to the

scheduled hearing, the government released Castaneda on her own

recognizance.

                                  B.

            Clayton Gordon is a native and citizen of Jamaica.

Gordon arrived in the United States as a lawful permanent resident

in 1982, at the age of six.    Between 1994 and 1999, Gordon served

in the National Guard and on active duty with the U.S. Army.      He

received an honorable discharge in 1999.

            Gordon was arrested in 2008 after police found cocaine in

his home.     He was released from custody later that day.        He

subsequently pled guilty to possession of narcotics with intent to


                                 -14-
sell, a violation of Connecticut law.        See Conn. Gen. Stat. § 21a-

277(a). On September 30, 2009, Gordon was sentenced to seven years

imprisonment, execution suspended, with a three-year probationary

term.   He completed his probation in October 2012.        Since 2008, he

has developed significant ties to the community--in 2008, he met

the woman who has since become his fiance; they have a child

together, born in 2010; they own a home in Bloomfield, Connecticut;

he has developed a successful business; and he has worked on a

project   to   open   a   halfway    house   for   women   released   from

incarceration.

           Gordon was arrested and detained by ICE on June 20, 2013,

more than four years after his release from state custody.             The

stated basis for removal was 8 U.S.C. § 1227(a)(2)(A)(iii), which

states than an alien shall be deportable if he is convicted of any

aggravated felony after being admitted to the United States.

Gordon challenged his deportability, but was denied relief after an

immigration judge agreed that Gordon’s cocaine conviction was an

aggravated felony under § 1227(a)(2)(A)(iii).         Thereafter, Gordon

was held pursuant to the mandatory detention provision without

opportunity for a bond hearing to establish whether he may be

released during the removal proceedings.

           On August 8, 2013, Gordon filed a petition for writ of

habeas corpus in the District of Massachusetts.             The petition

argued that he was not subject to the mandatory detention provision


                                    -15-
because he was not taken into immigration custody “when . . .

released”     from    state    criminal      custody.       Gordon    sought    an

individualized       bond   hearing    at    which   he   could   establish    his

entitlement to release on bond.

            After a hearing, the district court granted Gordon’s

petition for writ of habeas corpus, instructing the government to

provide Gordon with a bond hearing.              The court held that “when

released” should be interpreted to mean “at the time of release,”

plus a reasonable time thereafter.              The court rejected the idea

that a five year gap was reasonable and rejected the government’s

argument that “when released” indicated the time at which it can

begin to act as “flatly implausible.”                Gordon was given a bond

hearing and was released on bond of $25,000 on November 18, 2013.6

                                        C.

            The government appeals, and we have jurisdiction under 28

U.S.C. § 1291.       We note that subsection 1226(e) prohibits judicial

review   of    “[t]he       Attorney   General’s      discretionary     judgment

regarding the application of [§ 1226],” including “any action or

decision . . . regarding the detention or release of any alien or

the grant, revocation, or denial of bond or parole.”                   8 U.S.C.



     6
          Gordon’s petition also sought class-wide relief for all
similarly situated individuals, but that claim is not before us.
The decision on appeal is the district court’s grant of Gordon’s
individual petition. The class-wide claims remain pending before
the district court.


                                       -16-
§ 1226(e).    But subsection (e) does not bar our review of this case

because Castaneda and Gordon do not challenge any “discretionary

judgment” of the Attorney General; rather, they challenge the

statutory basis for their detention.         Habeas petitions bringing

legal or constitutional challenges to an alien’s detention under

§ 1226 are not subject to subsection (e)’s prohibition of judicial

review.   Sylvain v. Attorney General, 714 F.3d 150, 155 n.4 (3d

Cir. 2013);     Singh v. Holder, 638 F.3d 1196, 1200-01 (9th Cir.

2011); Al-Siddiqi v. Achim, 531 F.3d 490, 494 (7th Cir. 2008);

Demore, 538 U.S. at 517.

                                  III.

             In these appeals the government asks for reversal of the

grant of habeas corpus to Castaneda and Gordon and a determination

that they are subject to mandatory detention.       In the government’s

view, § 1226(c) subjects an alien to detention without bail at any

time after release, including years later, and detention can

continue years after release while the alien fights removal.            We

think the government’s view of § 1226(c) is incorrect, and that in

Justice   Kennedy’s    phrase   the   government   in   these   cases   has

“unreasonabl[y] delay[ed] . . . in pursuing . . . deportation

proceedings.”     Demore, 538 U.S. at 532.

                                      A.

             We first address the meaning of the “when . . . released”

clause in § 1226(c).      The government admits that this language


                                  -17-
could mean immediately after release, but contends that this

language is ambiguous because it could also mean any time after,

but   not   before,   release.     According   to   the   government,‘when

released’ can plausible be read to “signif[y] that Congress did not

want DHS to preempt state and federal law enforcement officials by

trying to take criminal aliens into immigration custody before they

[c]ompleted their term of non-DHS criminal custody. . . .”                Gov’t

Gordon Br. 24.        The government argues that Chevron deference

requires adopting this construction.        The petitioners contend that

it unambiguously means “immediately” and no later than 48 hours.

We think neither interpretation is correct.

            The government’s proposed interpretation--“at any time

after release,” but not before release--is simply inconsistent with

the plain meaning of the term “when” in this context.             To be sure,

the term “when” can be used in different ways.            The Random House

Dictionary of the English Language lists three potentially relevant

senses: “at the time or in the event that,” “at any time that;

whenever,” and “upon or after which; and then.”                  Random House

Dictionary of the English Language 1626 (1981 ed.).                 See also

Webster’s    Third    New   International   Dictionary    2602    (1993   ed.)

(listing four: “at or during the time that,” “just after the moment

that,” “at any and every time that,” and “in the event that”);

American Heritage Dictionary 2032 (3d ed. 1992) (listing four: “at

the time that,” “as soon as,” “whenever,” and “during the time


                                    -18-
which; while”); 20 Oxford English Dictionary (“OED”) 209 (2d ed.

1989) (listing two principal senses: “[a]t the (or a) time at

which; on the (or an) occasion on which”).

          The government is correct in its assertion that one sense

of “when” is similar in meaning to the word “after,” that is, not

before.   The government contends that it is in this conditional

sense that the word “when” is used in this statute. The government

relies on dictionary definitions and cases pertaining to the use of

“when” in the conditional sense--meaning, roughly, “if” or “in the

event that.”   See Random House, supra, at 1626 (“at any time;

whenever”); 20 OED, supra, at 209 (“[i]ndefinitely or generally:

[a]t any time, or at the several times, at which; on any occasion

that”); Webster’s Third, supra, at 2602 (“in the event that : on

condition that”); American Heritage, supra, at 2032 (“[w]henever”);

Random House, supra, at 1626 (“upon or after which”).

          The Supreme Court’s decision in United States v. Willings

demonstrates both that the word “when” is not used in § 1226(c) in

the conditional sense and that, even if it were, the statute would

require detention within a reasonable period of time after release.

There, a federal maritime statute provided that “when any ship or

vessel . . . registered pursuant to this act . . . shall in whole

or in part be sold or transferred to a citizen, or citizens of the

United States . . . , in every such case the said ship or vessel

shall be registered anew.”     8 U.S. (4 Cranch) 48, 49 (1807)


                               -19-
(quoting Act of Dec. 31, 1792, § 14). In subsequent sentences, the

statute used the phrase “in every such case” or “in every case”

repeatedly.   See id.   Chief Justice Marshall explained that the

correct understanding of the word “when” in that statute was “that

it describes the occurrence which shall render [re-registration]

necessary,” rather than “designat[ing] the precise time when [re-

registration] must be performed.”     Id. at 55-56.

          In contrast to the statute at issue here, the statute in

Willings repeatedly employed the phrase “in every such case,”

strongly suggesting that “when” was intended in the conditional

sense, rather than the temporal sense.      We think it clear that

§ 1226(c) does not use the word “when” in the conditional sense, as

if to distinguish between a case where the alien is released from

state custody and a case where he is not.         The detention and

deportation of an alien under § 1226(c) is premised on the notion

that the alien has been released from state custody; there is no

need for § 1226(c) to specify it.       There was no congressional

concern in connection with subsection 1226(c) that the Attorney

General might detain the alien before release from state custody.

Indeed, Congress has already provided in 8 U.S.C. § 1231(a)(4)(A)

that an alien typically could not be detained before release from

state or federal custody.

          Willings, moreover, makes clear that “when,” used in the

conditional sense, means that the specified action must be taken


                               -20-
within a reasonable period of time after the triggering event or

condition.     Id. at 56 (rejecting that “when” means the “precise

time,” and explaining that a ship must be allowed “a reasonable

interval” of time after transfer or sale in which to register,

“depend[ing] on the nature of the case”).                  There is no textual

support for the government’s argument that “when . . . released”

means “at any time after release.”

             Nor do the structure, purpose, or legislative history of

the   statute       suggest    that        Congress     contemplated       automatic

detention’s being imposed years after an alien’s release from

custody.     The § 1226(c) cases on which the government relies for

support merely describe Congress’s generalized intent to detain

criminal aliens in order to protect the community and ensure swift

deportation.     See, e.g., Demore, 538 U.S. at 518-21; Sylvain, 714

F.3d at 159; Hosh v. Lucero, 680 F.3d 375, 381 (4th Cir. 2012).

But   this    court    explained      in    Saysana     that   such    generalized

statements of legislative intent “paint[] with far too broad a

brush” to be given controlling weight in interpreting § 1226.                   590

F.3d at 17.     “The mandatory detention provision does not reflect a

general    policy     in   favor   of      detention;    instead,     it   outlines

specific, serious circumstances under which the ordinary procedures

for release on bond at the discretion of the immigration judge

should not apply.”         Id. at 17.       So too here, we cannot adopt the

government’s interpretation of the statute just because Congress


                                        -21-
had a general concern for detaining criminal aliens “when . . .

released” from custody.

           When the government has delayed several years before

arresting an alien, the presumption of dangerousness and flight

risk is eroded by the years in which the alien lived peaceably in

the community.     As this court explained in Saysana,

     it is counter-intuitive to say that aliens with
     potentially longstanding community ties are, as a class,
     poor bail risks. The affected aliens are individuals who
     committed an offense, and were released from custody for
     that offense, more than a decade ago.         They have
     continued to live in the United States. By any logic, it
     stands to reason that the more remote in time a
     conviction becomes and the more time after a conviction
     an individual spends in a community, the lower his bail
     risk is likely to be.

590 F.3d at 17.7

           Finding no support in the statute’s text, structure,

purpose,   or   legislative   history,   we   reject   the   government’s

argument that “when . . . released” could mean “at any time after

release,” but not before release.8


     7
          The government contends that “[u]pon initiation of
removal proceedings, however, the threat of removal becomes real,
and the likelihood that a criminal alien will flee to evade
proceedings only begins at that moment.” Gordon Reply Br. at 10.
This theory is speculative and exists with respect to all
detainees, not only to detainees who have been convicted of a
predicate offense. Congress made no decision to apply mandatory
detention to all detainees who become potential flight risks when
detained. Rather, Congress focused on the predicate offense.
     8
          The government relies on In re Rojas, 23 I. & N. Dec. 117
(BIA 2001) for this construction, claiming that “[t]he BIA []
recognized that ‘when’ could mean . . . at or after the specified
point in time.” Gov’t Gordon Br. 17. We do not read Rojas as


                                 -22-
           This leads us to the petitioner’s interpretation.            While

we reject the “at any time after” interpretation, we also think

that, contrary to the petitioners, “when . . . released” does not

mean “immediately upon release, without interruption.”            Nothing in

subsection 1226(c) compels such a reading of the phrase.               As the

dictionaries show, the temporal sense of “when” typically connotes

a degree of immediacy.          See American Heritage, supra, at 2032

(defining “when” as “as soon as” and giving the following example:

“I’ll   call   you   when   I   get   there.”);   20   OED,   supra,   at   209

(“[s]ometimes implying suddenness: = and just then, and at that

moment”); Webster’s Third, supra, at 2602 (“just after the moment

that”).   This is confirmed by common usage.             One would not say

“stop writing when the bell rings” to mean “any time after the bell

rings, even hours later.”         See Webster’s Third, supra, at 2602

Thus, “when” in this context connotes temporal immediacy.                   See

Random House, supra, at 1626; 20 OED, supra, at 209; Webster’s

Third, supra, at 2602; American Heritage, supra, at 2032.                   But,

what constitutes immediacy is be determined by context.

           It seems quite unlikely that Congress intended § 1226(c)

to require the strict immediacy advocated by the petitioners.




interpreting “when” to mean “any time after.” Accord Sylvain v.
Attorney Gen., 714 F.3d 150, 157 n.9 (3d Cir. 2013) (“The Board [in
Rojas] did not explicitly interpret the word ‘when.’ If anything,
it suggested that ‘when’ denotes immediacy.”).



                                      -23-
Practically speaking, the government cannot always detain criminals

at the precise moment of their release from state custody. For one

thing,      such   immediate   detention     requires    foreknowledge   of   an

alien’s impending release from custody, for which the government

must depend on the cooperation of state and local authorities.

This cooperation is often less than perfect.             Indeed, at least one

state       adjacent   to   this   circuit    recently    passed   legislation

curtailing its cooperation with ICE in detaining aliens convicted

of crimes. See An Act Concerning Civil Immigration Detainers, Pub.

Act No. 13-155, § 1 (Conn. 2013) (codified at Conn. Gen. Stat.

§ 54-192h).        The government credibly argues that such action has

“great potential to impact ICE’s ability to identify criminal

aliens in state and local criminal custody.”              Castaneda Reply Br.

9 n.5.       It would make little sense to interpret the statute to

strictly require immediate detention in all cases, since that is an

impossible task, as Congress recognized.

               “Words, like syllables, acquire meaning not in isolation

but within their context.”          K-Mart v. Cartier, 486 U.S. 281, 319

(1988) (Scalia, J., concurring in part and dissenting in part).9

Based on the textual context, we interpret § 1226(c) as requiring

that criminal aliens be detained within a reasonable time after



        9
          “[Text] should be construed reasonably, to contain all
that it fairly means.” Scalia, J., A Matter of Interpretation,
(1997).


                                      -24-
their release from state criminal custody, and that what is a

reasonable time must account for the inherent difficulties in

identifying and locating an alien upon release from state custody.

The statute does not tolerate unreasonable delays, but neither does

it require strict immediacy.

             As in Willings, the reasonable time within which the

government must detain an alien to satisfy the “when . . .

released” clause will depend on the practical necessities at hand.

Since what is reasonable under the circumstances is not defined in

the statute, we think the statute is ambiguous in that respect. As

in   other   cases   of   statutory    ambiguity,   the   Attorney    General

therefore has considerable latitude to define what constitutes a

reasonable time under the Chevron framework.

             Under Chevron, the interpretation must be a reasonable

interpretation of the statute.          Chevron, U.S.A. v. Natural Res.

Def. Council, Inc., 467 U.S. 837, 845 (1984).          As discussed above,

“when . . . released” cannot mean “any time after release.”            Nor do

we   think   it   would   be   a   reasonable   interpretation   to   view   a

reasonable period of time as including a delay of several years.

As we discuss below, the objectives of the statute are inapplicable

in such situations and enforcing such detentions would be arbitrary

in the extreme.      We think it plain that the petitioners were not

detained within a reasonable time after their detention, and that




                                      -25-
the “when . . . released” clause was not satisfied here.10 Here, as

in Saysana, this court is “not persuaded that the legislature was

seeking to justify mandatory immigration custody many months or

even years after an alien had been released from state custody.”



     10
          The government’s briefs focus on the question of whether
the “when . . . released” clause is satisfied by the detention of
an alien years after release from state custody.            In the
alternative, the government argues that paragraph (2) of subsection
(c), bars release of the alien regardless whether the alien was
taken into custody pursuant to paragraph (1).        See 8 U.S.C.
§ 1226(c)(2) (“The Attorney General may release an alien described
in paragraph (1) only if [narrow conditions are met].”).        The
government argues that the statute is ambiguous in that respect and
that we must therefore defer to the BIA’s decision in Rojas that
paragraph (2) works independently of paragraph (1). We reject this
argument because it is inconsistent with the language of the
statute. On its face, paragraph (2) refers to aliens taken into
custody pursuant to paragraph (1).      If Congress had wanted to
include a provision barring release of any alien who had committed
a predicate act, Congress could simply have said “Any alien
described in paragraphs (A) through (D) . . . .” The fact that
Congress did not use the more natural and condensed wording
suggests it had another purpose. Congress’ decision to only make
1226(c) apply prospectively to predicate offenses committed after
enactment also refutes the government’s construction.

           Moreover, this court already rejected that argument in
Saysana.    In that case, the issue was “whether the mandatory
detention provision applies only when an alien is released from a
criminal custody the basis for which is one of the [listed
predicate offenses]; or, [] whether it applies whenever [such] an
alien . . . is released from any criminal custody regardless of the
reason for that detention.” 590 F.3d at 11. The court emphasized
“[r]esolution of this issue centers on the ‘when released’ language
in § 1226(c).” Id. Saysana thus recognized that the “when . . .
released” language of paragraph (1) is essential to determining
whether an alien is subject to mandatory detention. If paragraph
(2) operated independently of paragraph (1), as Rojas and the
government would have it, there would have been no reason for
Saysana to consider the “when . . . released” language in its
analysis.


                               -26-
Saysana, 590 F.3d at 16 (quoting Quezada-Bucio v. Ridge, 317 F.

Supp. 2d 1221, 1230 (W.D. Wash. 2004)).11

                                      B.

           Notwithstanding           our      conclusion         that      the

“when . . . released” requirement was not met here, the government

claims support in a line of Supreme Court cases holding that

failure to comply with a statutory deadline did not deprive the

government of authority to act.            See, e.g., Barnhart v. Peabody

Coal Co., 537 U.S. 149, 158-63 (2003); United States v. Montalvo-

Murillo, 495 U.S. 711, 717-720 (1990).           Those so-called “loss of

authority” cases do not support the government’s view that aliens

are subject to mandatory detention even when the requirements of

§ 1226(c) are not complied with.

           In our view, those loss of authority cases fall into two

discrete categories.    On the one hand there are cases that involve

housekeeping     provisions--that     is,    time   limitations    that    are

procedural, horatory, advisory, or precatory, and are designed to

regulate   the    functioning   of    the    government    and    “spur”   the

government into action (see Brock v. Pierce Cnty. 476 U.S. 253, 265


     11
          We do not read Hosh or Sylvain as coming to a contrary
conclusion. Hosh only addressed whether “when” meant immediately,
and, as we do today, held that “when,” in this context, does not
require strict immediacy.   Hosh never stated that “when” is an
entirely open-ended time period; indeed, the court acknowledged
that the statute “connotes some degree of immediacy”. Hosh, 680
F.3d at 381. Sylvain failed to even address the meaning of “when.”
Sylvain, 714 F.3d at 157.


                                     -27-
(1986)), rather than to confer rights on regulated parties.                An

example of such a case is Barnhart, where the Court held that the

Commissioner of Social Security retained authority to take certain

actions under the Coal Industry Retiree Health Benefit Act despite

failure to comply with the statutory deadline. 537 U.S. at 158-63.

Similarly, in Brock, the Court upheld the Secretary of Labor’s

authority to order the repayment of misused grant funds even though

the audit that led to the repayment order was not completed within

the time given by the statute.         476 U.S. at 266.   The general rule

in such cases is that, “if a statute does not specify a consequence

for noncompliance with statutory timing provisions, the federal

courts will not in the ordinary course impose their own coercive

sanction.”     United States v. James Daniel Good Real Property, 510

U.S. 43, 63 (1993).

             On the other hand, there is another category of cases

such    as    Montalvo-Murillo,   in    which   the   statute   is   not    a

housekeeping provision but is rather designed to protect the rights

of individuals.     In such circumstances a more nuanced approach is

required.12


       12
          See French v. Edwards, 80 U.S. 506, 511 (1871), which
explained that provisions “designed to secure order, system, and
dispatch proceedings” “are not usually regarded as mandatory unless
accompanied by negative words,” “[b]ut when the requisitions
prescribed are intended for the protection of the citizen,” and
that “a disregard of which his rights might be and generally would
be injuriously affected,” the provisions “are not directory but
mandatory.” Id.


                                   -28-
          We first address whether this statute falls in the

housekeeping category.   Two other circuits have concluded that it

does, and therefore ruled that aliens such as the petitioners were

subject to mandatory detention despite years-long delays by the

government.   See Sylvain, 714 F.3d at 159 (“[T]he mandatory-

detention statute is intended to protect only the public . . . .”);

Hosh, 680 F.3d at 382 (“[Section] 1226 was undeniably not written

for the benefit of criminal aliens facing deportation like Hosh.”

(emphasis removed)).   We disagree.

          In determining the congressional purpose behind § 1226(c)

we must consider not only the provision’s legislative history

(which admittedly does not suggest a purpose to benefit alien

detainees) but also constitutional considerations.      We think    the

“when . . . released” clause must be construed as benefitting

aliens   detained   years    after    release   in   order   to    avoid

constitutional doubts.      Avoidance of constitutional doubt is a

“cardinal principle of statutory interpretation.”       Zadvydas, 533

U.S. at 689 (quoting Crowell v. Benson, 285 U.S. 22, 62, (1932)

(internal quotation marks omitted)).       As the Supreme Court has

explained countless times, “when an Act of Congress raises a

serious doubt as to its constitutionality, this Court will first

ascertain whether a construction of the statute is fairly possible

by which the question may be avoided.”     Id. (quoting Crowell, 285

U.S. at 62 (internal quotation marks omitted)).       This obligation


                                 -29-
requires us to attempt to find a constitutional purpose as well as

a constitutional construction of the words of the statute.                    SKF

USA, Inc. v. U.S. Customs and Border Protection, 556 F.3d 1337,

1353 (Fed. Cir. 2009).     We follow that guidance here.

            Justice Kennedy cautioned in Demore that, “since the Due

Process Clause prohibits arbitrary deprivations of liberty, a

lawful permanent resident alien . . . could be entitled to an

individualized     determination    as    to   his     risk   of   flight     and

dangerousness if the continued detention became unreasonable or

unjustified.”      538 U.S. at 532 (Kennedy, J., concurring).                  He

continued: “Were there to be an unreasonable delay by [ICE] in

pursuing and completing deportation proceedings, it could become

necessary   then   to   inquire    whether     the    detention    is   not   to

facilitate deportation, or to protect against risk of flight or

dangerousness, but to incarcerate for other reasons.”              Id.13    As a

constitutional matter, mandatory detention can only be justified by

the presumption of dangerousness and flight risk posed by newly

released criminal defendants.       But those who have resided in the

community for years after release cannot reasonably be presumed

either to be dangerous or flight risks.              This is particularly so


     13
          While Justice Kennedy’s concerns were limited to the case
of “a lawful permanent resident alien,” id. at 532, which Castaneda
is not, we do not interpret the mandatory detention provision
differently as to her or other unlawful or non-permanent resident
aliens.   The text of the statute provides no basis for such a
distinction.


                                   -30-
given the breadth of offenses to which 1226(c) applies, and the

inclusion   of   offenses       such    as     non-violent     drug   possession.

Mandatory detention of such individuals years after release for

such    crimes   raises       serious    constitutional        questions.      The

government acknowledged at oral argument the harsh consequences of

“uprooting these individuals from the community,” a feature which

only underscores the arbitrary nature of the detention.14

            Despite     its    years-long         delay   in   bringing     removal

proceedings after the petitioners’ release from criminal custody,

the government has offered no explanation for either the delay or

the eventual decision to prosecute in these individual cases or,

for that matter, in the other cases where individuals have been

detained years after release.             Indeed, when the district court

ordered that the petitioners be given bond hearings, the government

released each one, thereby indicating that the government actually

viewed them as neither dangerous nor likely to flee. Castaneda was

even released on her own recognizance (i.e., without a monetary

bond) and before her bond hearing even took place.

            Mandatory     detention          of    individuals    such    as    the

petitioners appears arbitrary on its face.                We are left to wonder


       14
          We also note other circuits have raised significant
constitutional concerns associated with arbitrary application of
the statute where long-term detention occurs and have construed
1226(c) as not applying in such circumstances.        See Casas-
Castrillon v. Dept. of Homeland Sec., 535 F.3d 942, 950 (9th Cir.
2008); Ly v. Hansen, 351 F.3d 263, 272 (6th Cir. 2003).


                                        -31-
whether the petitioners’ sudden arrest and detention is not “to

facilitate deportation, or to protect against risk of flight or

dangerousness, but to incarcerate for other reasons,” which would

offend due process.         Zadvydas, 533 U.S. at 690.           Under these

circumstances, we think § 1226(c) must be interpreted as designed

to benefit alien detainees who were detained years after release

from criminal custody in order to avoid constitutional concerns.

            The government argues that even if § 1226(c) is not a

housekeeping provision, but instead is read to benefit aliens who

were    released    years   earlier,    Montalvo-Murillo        supports    its

position. There, the Supreme Court addressed the Bail Reform Act’s

requirement that a suspect held in pretrial custody must be given

a bail hearing “immediately upon the person’s first appearance,” a

provision designed to protect the rights of criminal defendants.

495 U.S. at 714 (quoting 18 U.S.C. § 3142(f) (1988)).             The Supreme

Court    nevertheless    concluded   that   the   failure   to    provide   an

immediate bail hearing did not deprive the government of all

authority to hold the defendant. The Court expressed concern that,

in     ordering    the   suspect’s   release,     the   lower    courts     had

“invent[ed]” a remedy unsupported by the statutory text: “Neither

the timing requirements nor any other part of the Act can be read

to require, or even suggest, that a timing error must result in

release of a person who should otherwise be detained.” Id. at 716-

17, 721.    Even if some remedy were required, the Court explained,


                                     -32-
“[w]e need seek only a practical remedy, not one that strips the

Government of all authority to act.”        Id. at 719.      “When, as here,

there are less drastic remedies available for failure to meet a

statutory deadline, courts should not assume that Congress intended

the agency to lose its power to act.”        Id. at 718 (quoting Brock,

476 U.S. at 260 (internal quotation marks omitted)).

              The cases before us stand in stark contrast to Montalvo-

Murillo, and the absence of the factors the Court found compelling

there dictates the opposite result here.               First, the district

courts here did not “invent” a remedy unsupported by the statute’s

text.    Rather, the grant of limited habeas relief requiring a bond

hearing reflected the structure of the detention provisions as a

whole.    Mandatory detention under subsection (c) is an exception;

general detention under subsection (a) is the default rule.              See

§ 1226(a) (“Except as provided in subsection (c) . . . .”).               If

subsection (c) does not apply, it follows naturally that subsection

(a) does, and that the petitioners must be given a bond hearing.

So unlike in Montalvo-Murillo, the remedy here comports with the

text and structure of the statute.

              Second,   unlike   Montalvo-Murillo,     the   district   court

decisions here did not strip the Attorney General of authority to

detain the petitioners. Under section 1226(a) the Attorney General

has   broad     and   unreviewable   discretion   to    determine    whether

individual aliens should be afforded release on bond.               8 U.S.C.


                                     -33-
§ 1226(a)(1)-(2) (stating that the Attorney General “may continue

to detain the arrested alien” and “may release the alien” on bond

or parole, but placing no constraints on the Attorney General’s

decision);    id   §   1226(e)   (prohibiting   judicial     review).    In

exercising this discretion, the Attorney General may adopt any

regulation that “has a ‘reasonable foundation,’” meaning that it

“rationally pursues a purpose that it is lawful . . . to seek.”

Reno v. Flores, 507 U.S. 292, 309 (1993) (quoting Carlson v.

Landon, 342 U.S. 524, 541 (1952)).         The grant of habeas relief in

these   cases   merely   forced   the   Attorney   General    to   consider

releasing the petitioners.       He retained full authority to decline.

             Third, unlike Montalvo-Murillo, the remedy here is not

drastic.   The lower courts in Montalvo-Murillo “mandat[ed] release

of possibly dangerous defendants.”         Montalvo-Murillo, 495 U.S. at

720.    The district courts here did no such thing.           They did not

order the petitioners’ release; they ordered that the petitioners

be given a hearing at which the government has discretion to

continue their detention if it finds them dangerous or a flight

risk.    It was the government itself that determined to release

Castaneda and Gordon.

             In light of these significant differences, we think that

Montalvo-Murillo does not apply here, and that violating the

command of the statute for detention “when . . . released” is

properly enforced by requiring an individualized hearing.


                                    -34-
                                IV.

          Section 1226(c) requires detention of aliens such as the

petitioners “when . . . released.”      Because the petitioners were

not timely detained under any reasonable interpretation of the

statute, we conclude that the petitioners are not subject to

mandatory detention under § 1226(c).     They are not subject to an

irrebuttable presumption of dangerousness and flight risk, but are

rather entitled to an individualized determination by the Attorney

General of such factors.   We therefore affirm the decisions of the

district courts granting habeas relief to the petitioners.15

                             AFFIRMED

          Costs to appellees.




     15
          We note in conclusion that many district courts across
the country have adopted the interpretation of § 1226(c) that we
adopt today. See, e.g., Alikhani v. Fasano, 70 F. Supp. 2d 1124,
1130 (S.D. Cal. 1999); Ortiz v. Holder, No. 2:11-cv-1146 DAK, 2012
WL 893154, at *3-4 (D. Utah Mar. 14 2012); Harris v. Lucero, Civil
Action No. 1:11-cv-692, 2012 WL 603949, at *3 (E.D. Va. Feb 23,
2012); Parfait v. Holder, Civil No. 11-4877 (DMC), 2011 WL 4829391,
at *4-9 (D.N.J. Oct. 11, 2011); Rianto v. Holder, No. CV-11-0137-
PHX-FJM, 2011 WL 3489613, at *3 (D. Ariz. Aug. 9, 2011). Indeed,
that interpretation appears to be the majority view. See Sylvain,
714 F.3d at 157 (collecting cases).


                                -35-
