Court Opinion

ID: 4298125
Source: CourtListenerOpinion
Date Created: 2018-07-26 17:00:36.589756+00
Date Added: 2024-06-11T13:26:01.148870
License: Public Domain

FOR PUBLICATION

  UNITED STATES COURT OF APPEALS
       FOR THE NINTH CIRCUIT

FRIMMEL MANAGEMENT,                     No. 16-73906
LLC,
              Petitioner,             DHS-1
                                   OCAHO Case No.
            v.                       15A00073

UNITED STATES OF AMERICA;
U.S. DEPARTMENT OF                       OPINION
HOMELAND SECURITY;
IMMIGRATION AND CUSTOMS
ENFORCEMENT,
              Respondents.

      On Petition for Review of an Order of the
         Department of Homeland Security

        Argued and Submitted April 10, 2018
             San Francisco, California

                  Filed July 26, 2018

   Before: Dorothy W. Nelson, William A. Fletcher,
       and Raymond C. Fisher, Circuit Judges.

           Opinion by Judge D.W. Nelson
2             FRIMMEL MGMT. V. UNITED STATES

                            SUMMARY*

           Immigration/Employment Verification

    The panel granted a petition for review of an
Administrative Law Judge’s final decision and order in a
proceeding before the Office of the Chief Administrative
Hearing Officer of the Executive Office for Immigration
Review declining to suppress employment records
Immigration and Customs Enforcement obtained through an
investigation of Frimmel’s compliance with employment
verification requirements.

    ICE initiated an investigation of Frimmel after the
Maricopa County Sheriff’s Office (“MCSO”), under Sheriff
Joe Arpaio, conducted illegal raids of two restaurants and the
home of Bret Frimmel, owner of Frimmel Management.
MCSO later e-mailed a Shift Summary to ICE, and issued
press releases revealing the results of the raids.

    The panel explained that, even in administrative
proceedings in which the exclusionary rule does not
ordinarily apply, administrative tribunals are still required to
exclude evidence that was obtained by deliberate violations
of the Fourth Amendment, or by conduct a reasonable officer
should know is in violation of the Constitution. The panel
noted that Frimmel was not arguing for suppression of its
identity, but rather suppression of the evidence ICE obtained
when ICE conducted an audit after MCSO issued press
releases and sent ICE an e-mail with its Shift Summary.

    *
      This summary constitutes no part of the opinion of the court. It has
been prepared by court staff for the convenience of the reader.
            FRIMMEL MGMT. V. UNITED STATES                    3

    The panel held that omissions and distortions in MCSO’s
search warrant affidavits violated the Fourth Amendment, and
because a reasonable officer should have known the conduct
was unconstitutional, the violation was egregious. The panel
also concluded that ICE’s evidence was the fruit of MCSO’s
unlawful search.

    In considering whether the attenuation doctrine applied as
an exception to the exclusionary rule, the panel considered
temporal proximity, and noted that the ICE investigation
closely followed the unconstitutional search. The panel also
considered whether there were intervening circumstances that
purged the taint of the unlawful search, and concluded that
the ICE investigation was not an intervening circumstance,
rather, it was itself a direct result of MCSO’s earlier unlawful
search, and based on MCSO’s communication to ICE and
publicizing of the raid, the ICE investigation was precisely
what MCSO intended. The panel also concluded that
MCSO’s conduct was flagrantly illegal, and that MCSO had
immigration enforcement as its primary zone of interest. The
panel held that ICE’s investigation was therefore not
attenuated from MCSO’s illegal raid.

    The panel concluded that application of the exclusionary
rule would serve to deter MCSO from Fourth Amendment
violations by the probability that illegally obtained evidence
would not be useful to ICE, even in a civil proceeding.

    The panel reversed the ALJ’s ruling denying suppression
of ICE’s evidence pursuant to the exclusionary rule, and
remanded for further proceedings.
4           FRIMMEL MGMT. V. UNITED STATES

                        COUNSEL

Andrew S. Jacob (argued), Gordon Rees Scully Mansukhani,
LLP, Phoenix, Arizona, for Petitioner.

Andrew N. O’Malley (argued), Senior Litigation Counsel;
Surell Brady, Trial Attorney; Chad A. Readler, Acting
Assistant Attorney General; Office of Immigration Litigation,
Civil Division, United States Department of Justice,
Washington, D.C.; for Respondents.

                         OPINION

D.W. NELSON, Senior Circuit Judge:

                        OVERVIEW

    Frimmel Management, LLC (“Frimmel”) seeks review of
the Administrative Law Judge’s (“ALJ”) final decision and
order declining to suppress employment records Immigration
and Customs Enforcement (“ICE”) obtained through an
investigation of Frimmel’s compliance with employment
verification requirements. ICE initiated the investigation
after the Maricopa County Sheriff’s Office (“MCSO”), under
Sheriff Joe Arpaio, conducted illegal raids of two restaurants
and the home of Bret Frimmel, owner of Frimmel
Management. MCSO later e-mailed a Shift Summary to ICE
and also issued press releases revealing the results of the
raids. We GRANT the petition for review, REVERSE the
ALJ’s ruling that ICE’s evidence in the civil proceedings
should not be suppressed pursuant to the exclusionary rule,
VACATE the judgment, and REMAND.
            FRIMMEL MGMT. V. UNITED STATES                   5

                      BACKGROUND

I. State Court Suppresses MCSO’s Evidence

    On July 17, 2013, MCSO, under Sheriff Joe Arpaio,
raided two Uncle Sam’s restaurant locations, where Frimmel
Management leased employees, and the home of Bret
Frimmel, owner of Frimmel Management. MCSO deputies
seized employment records based on suspicion that the
restaurants hired people who committed identity theft and
forgery to obtain employment at Uncle Sam’s.

    The State of Arizona then prosecuted Frimmel for
violating Arizona’s identity theft laws. At an evidentiary
hearing, the Maricopa County Superior Court found that eight
omissions and distortions in the affidavits that supported the
search warrant for the raids were “unreasonable and
reckless.” After reforming the affidavits, the state court held
that there was no probable cause to support the warrants and
dismissed the criminal charges against Frimmel.

II. ICE Audit       of    Frimmel     and     Administrative
    Proceedings

    On July 18, 2013, the day after MCSO conducted the
raids, MCSO sent various ICE officials, including ICE
Auditor Ryan Miller, a Shift Summary reporting the results
of the unlawful search. On July 17, 2013 and July 18, 2013,
MCSO issued a press release publicizing the raids and stated
that “[n]ine of the suspects have had ICE holds placed on
them.”

    On August 9, 2013, ICE served Frimmel with a Notice of
Inspection and an Immigration Enforcement Subpoena. The
6           FRIMMEL MGMT. V. UNITED STATES

Immigration Enforcement Subpoena requested that Frimmel
provide the original Employer Verification Forms I-9 for all
current and former employees, copies of any identity and
employment authorization documents attached to the
employees’ Forms I-9, a list of all employees receiving wages
from August 9, 2010 to the date of the Notice of Inspection,
and other related employee and business records. Bret
Frimmel submitted a stack of Forms I-9 to ICE on August 12,
2013.

    This investigation resulted in ICE filing a complaint with
the Office of the Chief Administrative Hearing Officer of the
Executive Office for Immigration Review (“OCAHO”),
alleging that Frimmel Management violated various
provisions of § 274A of the Immigration and Nationality Act,
8 U.S.C. § 1324a(a)(1)(B) and its corresponding regulations.
ICE Auditor Ryan Miller stated that the audit of Frimmel was
“initiated based [on] information generated from local
television news channels and local news internet websites.”

    Frimmel attempted to depose the employees at ICE who
received the Shift Summary to determine why MCSO sent its
Shift Summary to ICE. The Government then moved for a
protective order. Over Frimmel’s objections, the ALJ issued
that protective order, reasoning that the effects of ICE
receiving this e-mail were immaterial because Frimmel’s
identity was not suppressible. The ALJ further ruled that
whether Frimmel came to the attention of ICE auditors “as a
result of an allegedly unlawful police action perpetrated by
MCSO is irrelevant to the case filed with OCAHO.”
              FRIMMEL MGMT. V. UNITED STATES               7

III.      ALJ’s Summary Decision

    On May 25, 2016, the Government filed a Motion for
Summary Decision. Frimmel opposed that motion, arguing
that the Government’s material evidence must be suppressed
under fruit of the poisonous tree doctrine.

    A second ALJ then issued a Final Decision and Order on
October 14, 2016 that substantially incorporated the
reasoning in the first ALJ’s protective order. The ALJ first
ruled that Frimmel’s identity was not suppressible. The ALJ
further found that “[t]here is no evidence to suggest that
Auditor Miller failed to carry out this investigation in
accordance with DHS guidelines or that he relied on evidence
directly obtained from MCSO’s unlawful conduct,” and
therefore concluded that Frimmel did not establish that ICE’s
evidence “constitutes fruit of the poisonous tree.”

    The ALJ went on to reason that even assuming the
evidence was fruit, it was too attenuated from MCSO’s
unlawful conduct because ICE obtained its evidence “as a
direct result of an independent investigation carried out by
ICE’s [Homeland Security Investigations Unit], an entity
wholly separate from MCSO. The ALJ then determined that
Frimmel “failed to show that suppression of the challenged
evidence would satisfy the exclusionary rule’s primary goal
of deterring future unlawful police conduct” because the
“OCAHO proceeding is not within the ‘zone of primary
interest’ of the MCSO [deputies], who sought criminal
convictions based on Arizona’s identity theft laws.”

       Frimmel petitioned for review.
8          FRIMMEL MGMT. V. UNITED STATES

                STANDARD OF REVIEW

    We review de novo the ALJ’s conclusions of law,
including whether the exclusionary rule applies in a civil
proceeding. See Mester Mfg. Co. v. INS, 879 F.2d 561, 565
(9th Cir. 1989) (citations omitted). “Within the de novo
framework, however, we give a certain amount of deference
to an agency’s reasonable construction of a statute it is
charged with administering.” Id. (citing FTC v. Indiana
Fed’n of Dentists, 476 U.S. 447, 454 (1986)). We review for
substantial evidence the ALJ’s findings of fact. Id.

                      DISCUSSION

I. MCSO Committed an Egregious Fourth Amendment
   Violation

     The Fourth Amendment “safeguard[s] the privacy and
security of individuals against arbitrary invasions by
governmental officials.” Carpenter v. United States,
589 U.S. ___, No. 16-402, 2018 WL 3073916, at *5 (June 22,
2018) (quoting Camara v. Mun. Court of City & Cty. of S.F.,
387 U.S. 523, 528 (1967)). “It is well settled that evidence
seized during an unlawful search cannot constitute proof
against the victim of the search.” United States v. Crews,
502 F.3d 1130, 1135 (9th Cir. 2007) (citing Wong Sun v.
United States, 371 U.S. 471, 484 (1963)). This exclusionary
rule extends not just to “evidence seized during an unlawful
search,” but also to the “indirect . . . products of such
invasions.” Wong Sun, 371 U.S. at 484.

   In INS v. Lopez-Mendoza, the Supreme Court held that
the exclusionary rule typically does not apply in
administrative—specifically, deportation—proceedings.
            FRIMMEL MGMT. V. UNITED STATES                    9

468 U.S. 1032, 1050 (1984). But “the Court expressly left
open the possibility that the exclusionary rule might still
apply in cases involving ‘egregious violations of Fourth
Amendment or other liberties that might transgress notions of
fundamental fairness and undermine the probative value of
the evidence obtained.’” Orhorhaghe v. INS, 38 F.3d 488,
492–93 (9th Cir. 1994) (quoting Lopez-Mendoza, 468 U.S. at
1050–51).

    We later interpreted the “egregiousness” caveat in Lopez-
Mendoza and established that egregious Fourth Amendment
violations warrant the application of the exclusionary rule in
civil proceedings. Adamson v. C.I.R., 745 F.2d 541, 545–46
(9th Cir. 1984). We “first emphasized that the Court [in
Lopez-Mendoza] based its general holding on its conclusion
that the exclusionary rule will have little deterrent effect in
the civil context.” Gonzalez-Rivera v. INS, 22 F.3d 1441,
1448 (9th Cir. 1994). We then “held that, even in
administrative proceedings in which . . . the exclusionary rule
[does not ordinarily apply], administrative tribunals are still
required to exclude evidence that was obtained by deliberate
violations of the Fourth Amendment or by conduct a
reasonable officer should know is in violation of the
Constitution.” Lopez-Rodriguez v. Mukasey, 536 F.3d 1012,
1015 (9th Cir. 2008) (quoting Orhorhaghe, 38 F.3d at 493).
Thus, “an egregious Fourth Amendment violation warrants
suppression . . . even if the seized evidence is highly reliable
and probative.” Orhorhaghe, 38 F.3d at 502.

    To decide whether MCSO deputies committed an
“egregious violation” of Frimmel’s rights, “we must first
determine whether [MCSO] violated the Fourth Amendment.
If [it] did, then we must determine whether [MCSO]
committed the violations deliberately or by conduct a
10          FRIMMEL MGMT. V. UNITED STATES

reasonable officer should have known would violate the
Constitution.” Lopez-Rodriguez, 536 F.3d at 1016 (quoting
Orhorhaghe, 38 F.3d at 493).

     a. MCSO’s Knowing or Reckless Material Omissions
        and Distortions in Search Warrant Affidavits
        Resulted in a Search Violating the Fourth
        Amendment

    “It is established law that a warrant affidavit must set
forth particular facts and circumstances underlying the
existence of probable cause, so as to allow the magistrate to
make an independent evaluation of the matter.” Franks v.
Delaware, 438 U.S. 154, 165 (1978) (citations omitted). A
search warrant, to be valid, must be supported by an affidavit
establishing probable cause.” United States v. Stanert,
762 F.2d 775, 778 (9th Cir.), amended, 769 F.2d 1410 (9th
Cir. 1985).

        To prevail on a claim that the police procured
        a warrant through deception, the party
        challenging the warrant must show that the
        affiant deliberately or recklessly made false
        statements or omissions that were material to
        the finding of probable cause. See Ewing v.
        City of Stockton, 588 F.3d 1218, 1223 (9th
        Cir. 2009). Our evaluation of materiality
        requires that we consider the effect of any
        false statements or omissions. “If an officer
        submitted false statements, the court purges
        those statements and determines whether what
        is left justifies issuance of the warrant.” Id. at
        1224. “If the officer omitted facts required to
        prevent technically true statements in the
            FRIMMEL MGMT. V. UNITED STATES                  11

       affidavit from being misleading, the court
       determines whether the affidavit, once
       corrected and supplemented, establishes
       probable cause.” Id.

United States v. Ruiz, 758 F.3d 1144, 1148 (9th Cir. 2014).
If the corrected warrant is lacking in probable cause, then
“the search warrant must be voided and the fruits of the
search excluded to the same extent as if probable cause was
lacking on the face of the affidavit.” Franks, 438 U.S. at 156.
“To credit a confidential source’s information in making a
probable cause determination, the affidavit should support an
inference that the source was trustworthy and that the
source’s accusation of criminal activity was made on the
basis of information obtained in a reliable way.” United
States v. Landis, 726 F.2d 540, 543 (9th Cir. 1984). “[B]y
reporting less than the total story, an affiant can manipulate
the inferences a magistrate will draw . . . [T]o allow a
magistrate to be misled in such a manner could denude the
probable cause requirement of all real meaning.” Ruiz,
758 F.3d at 1148 (citations and quotation marks omitted).
Omissions that undermine the credibility of complainants are
material to the finding of probable cause. See Illinois v.
Gates, 462 U.S. 213, 239 (1983) (reiterating that mere
statements that “affiants have received reliable information
from a credible person and believe that heroin is stored in a
home” is not sufficient (citations and quotation marks
omitted)).

    The Government does not dispute that the omissions and
distortions in MCSO’s affidavits were reckless and material.
MCSO omitted that Complainant #1 had called in her
complaint the day her husband was arrested for stealing from
Frimmel. MCSO also omitted that Complainant #2 was
12          FRIMMEL MGMT. V. UNITED STATES

previously arrested for stealing from Frimmel. These
omissions “suggest[] the possibility that [the Complainants]
would lie to the police to frame an innocent man,” here,
Frimmel. United States v. Hall, 113 F.3d 157, 160 (9th Cir.
1997). Further, Detective Henderson withheld the fact that
both complainants were anonymous tipsters, rather than
confidential informants. Detective Henderson also withheld
that an IRS investigation resulted in no findings of
wrongdoing against Frimmel and “wrongfully stated in the
affidavits that Complainant #2 was positive that no
employees had to fill out the A-4 state tax form,” even though
Complainant #2 never made such a statement. Given that
nothing corroborated the anonymous tips—and MCSO
actually withheld information that undermined the credibility
of those tips—the inaccuracies in the affidavits were material.
As the state court correctly found, all the foregoing omissions
and inaccuracies were either intentional or reckless given how
significant they were. Based on the foregoing, we also hold
that the MCSO raids that resulted from these reckless and
material inaccuracies constitute a Fourth Amendment
violation.

     b. The Fourth Amendment Violation Was Egregious
        because MCSO Acted Unreasonably

    The Government also concedes that MCSO’s conduct was
an egregious Fourth Amendment violation. As stated above,
“a Fourth Amendment violation is egregious if evidence is
obtained by deliberate violations of the [F]ourth
[A]mendment, or by conduct a reasonable officer should
[have known] is in violation of the Constitution.” Lopez-
Rodriguez, 536 F.3d at 1018 (citation, quotation marks, and
emphasis omitted).
            FRIMMEL MGMT. V. UNITED STATES                   13

    Under Franks, a police officer who recklessly disregards
the truth or knowingly includes false material information in,
or omits material information from, a search warrant affidavit
“cannot be said to have acted in an objectively reasonable
manner.” Branch v. Tunnell, 937 F.2d 1382, 1387 (9th Cir.
1991) (quoting Olson v. Tyler, 771 F.2d 277, 281 (7th Cir.
1985)), overruled on other grounds by Galbraith v. County of
Santa Clara, 307 F.3d 1119, 1127 (9th Cir. 2002). In other
words, if an officer recklessly omits or falsifies material
information, the officer has acted unreasonably and thus the
officer’s actions are sufficient to qualify as egregious conduct
under Adamson.

    As discussed above, MCSO made several reckless
material omissions or distortions in the affidavits. “Because
the [Franks] principle was firmly established at the time [the
MCSO detectives obtained the warrant and searched Uncle
Sam’s restaurants and the home of Bret Frimmel], we
conclude that a reasonable officer should have known that
both the seizure of [employment records] and the unlawful
entry into [Uncle Sam’s and Bret Frimmel’s home] violated
the Constitution.” Orhorhaghe, 38 F.3d at 503. We therefore
hold that MCSO’s “Fourth Amendment violations were
egregious.” Id.

II. ICE’s Investigation Is Not Attenuated from MCSO’s
    Illegal Raid

    The ALJ found, and the Government now argues, that
even assuming there was a Fourth Amendment violation, the
ICE investigation was too attenuated from MCSO’s illegal
conduct. There are three exceptions to the exclusionary rule
that implicate the causal relationship between the illegal act
and discovery of the evidence: 1) the independent source
14          FRIMMEL MGMT. V. UNITED STATES

doctrine; 2) the inevitable discovery doctrine; and 3) the
attenuation doctrine. Utah v. Strieff, 136 S. Ct. 2056, 2061
(2016). “To apply the exclusionary rule to the unique set of
facts presented here, we must consider the rule’s dual
purposes: to deter similar police misconduct in the future and
to preserve the integrity of the courts.” United States v.
$186,416.00 in U.S. Currency, 590 F.3d 942, 950 (9th Cir.
2010).

       “[U]nder the ‘attenuation doctrine,’ evidence is
admissible when ‘the connection between the illegality and
the challenged evidence’ has become so attenuated ‘as to
dissipate the taint caused by the illegality.’” United States v.
Gorman, 859 F.3d 706, 718 (9th Cir. 2017) (quoting United
States v. Ramirez-Sandoval, 872 F.2d 1392, 1396 (9th Cir.
1989)). “Of course, the line between taint and attenuation is
not an easy one to draw . . . [T]here is not now and doubtless
never will be any litmus-paper test for determining when
there is only an attenuated connection between a Fourth
Amendment violation and certain derivative evidence.”
United States v. Smith, 155 F.3d 1051, 1060 (9th Cir. 1998)
(citations and internal quotation marks omitted). The test,
however, “is more akin to a proximate causation analysis,”
rather than a “but for” test. Id.

     In determining whether evidence is too attenuated from
illegal conduct, relevant factors include: “[t]he temporal
proximity of the [MCSO raid] and [ICE’s evidence], the
presence of intervening circumstances, and, particularly, the
purpose and flagrancy of the official misconduct.” Brown v.
Illinois, 422 U.S. 590, 603–04 (1975) (citations omitted)
(emphasis added).
            FRIMMEL MGMT. V. UNITED STATES                   15

   1. ICE’s Evidence Is the Fruit of MCSO’s Illegal
      Raid

    “As a preliminary step, it is plain that the [evidence ICE
obtained] was the product of [MCSO’s] illegal activity.”
$186,416.00 in U.S. Currency, 590 F.3d at 951. “[E]vidence
qualifies as the ‘fruit of the poisonous tree’ when ‘the illegal
activity tends to significantly direct the investigation to the
evidence in question.’” Gorman, 859 F.3d at 716 (quoting
United States v. Johns, 891 F.2d 243, 245 (9th Cir. 1989)).
“‘The focus,’ in other words, ‘is on the causal connection
between the illegality and the evidence.’” Id. (quoting Johns,
891 F.2d at 245).

    In United States v. Johns, we held that evidence that
resulted from an investigation that was spurred by
identification evidence that “‘tended significantly’ to direct
the investigation toward the evidence in question” was fruit,
and also not attenuated from the earlier unlawful stop.
891 F.2d at 245 (quoting United States v. Bacall, 443 F.2d
1050, 1057 (9th Cir. 1971)). In Johns, Sheriff’s officers
illegally stopped two individuals at an airstrip. Id. at 244.
“As a result of the officers’ identification of Johns and
Hearron, Customs agents drew upon prior information about
Johns’ association with suspected narcotic smugglers and
quickly began surveillance at the house of one associate.
From the house, the agents followed several individuals to the
marijuana that was subsequently seized.” Id. (emphasis
added). Thus, we “[could not] hold that the role of the
identification was insignificant or de minimis, as the
government contend[ed].” Id. at 245 (emphasis omitted).

   “Here, there is an indisputable ‘causal connection’
between [MCSO’s unlawful search] and the [ICE
16           FRIMMEL MGMT. V. UNITED STATES

investigation] and its fruits.” Gorman, 859 F.3d at 716
(quoting Johns, 891 F.2d at 245). Auditor Miller testified
that he initiated the audit after MCSO issued a press release
publicizing the illegal raid. There were reports of Frimmel’s
violations on the tip line, but Auditor Miller’s testimony
shows that the ICE investigation was “initiated based on”
news reports rather than the tips. MCSO’s e-mail to ICE the
day after the illegal raid further supports our conclusion that
ICE initiated an audit “[a]s a result of” MCSO’s illegal
conduct. Id. at 716. Based on the information MCSO
conveyed to ICE, ICE “drew upon prior information about
[Frimmel] . . . and quickly began [an investigation].” Johns,
891 F.2d at 244. Like in Johns, the identity evidence that
resulted from the MCSO raid “significantly directed” the
subsequent investigation. Id. We therefore hold that ICE’s
evidence is the fruit of MCSO’s unlawful search.

    Both the Government and the ALJ focused on our rule
that identity evidence is not typically suppressible under the
Fourth Amendment. In United States v. Del Toro Gudino, we
held “that the simple fact of who a defendant is cannot be
excluded, regardless of the nature of the violation leading to
his identity. Other evidence, of course, may be suppressed
consistent with . . . our cases applying the exclusionary rule
in the criminal context.” 376 F.3d 997, 1001 (9th Cir. 2004)
(emphasis added).

     Here, Frimmel is not arguing for the suppression of its
identity; rather, it is arguing for suppression of the evidence
ICE obtained when ICE conducted an audit after MCSO
issued press releases and sent ICE an e-mail with its Shift
Summary. As discussed above, the evidence resulting from
a later investigation that is “significantly directed” by identity
evidence learned from earlier unlawful conduct is fruit of the
            FRIMMEL MGMT. V. UNITED STATES                    17

poisonous tree. See Johns, 891 F.2d at 245. Thus, the issue
concerns not suppression of identity evidence, but “[o]ther
evidence” that resulted from the unlawful raid. Del Toro
Gudino, 376 F.3d at 1001.

        2. Temporal Proximity

    Fruit may nonetheless be attenuated after considering the
three factors that guide the attenuation inquiry. Strieff, 136 S.
Ct. at 2061–62. As to the first factor, attenuation of
derivative evidence is favored when “substantial time elapses
between an unlawful act and when the evidence is obtained.”
Id. at 2062 (quoting Kaupp v. Texas, 538 U.S. 626, 633
(2003) (per curiam)). But there is “no bright-line test for
temporal proximity in an attenuation analysis” and even a two
month gap between an illegal search and the fruit may not
warrant a finding of attenuation. $186,416.00 in U.S.
Currency, 590 F.3d at 951 (citations and internal quotation
marks omitted) (holding that a two month gap between an
illegal search and a defendant’s subsequent declaration was
not sufficient to render the declaration attenuated from the
search). After MCSO conducted the illegal raid, MCSO e-
mailed the Shift Summary to ICE the next day and issued
press releases the day of the raid and the day after. As a
result of the raids, ICE initiated its investigation three weeks
and two days after. ICE’s investigation therefore “closely . . .
followed the unconstitutional search.” Strieff, 136 S. Ct. at
2062. Given that there is no bright line test, “we must
consider whether intervening circumstances may have purged
[ICE’s evidence] of taint from the illegal search.”
$186,416.00 in U.S. Currency, 590 F.3d at 951 (citing Brown,
422 U.S. at 603–04).
18          FRIMMEL MGMT. V. UNITED STATES

       3. Intervening Circumstances

    The second factor requires us to consider whether
intervening circumstances “purge the taint” of the MCSO
raid. United States v. Washington, 387 F.3d 1060, 1073 (9th
Cir. 2004). In United States v. Gorman, police officer
Monroe stopped Gorman based on a minor traffic infraction
and unlawfully prolonged the detention based on a suspicion
that Gorman was carrying drug money. 859 F.3d at 709.
Unable to justify a search of the car, Monroe communicated
identification information about the vehicle and Gorman to a
deputy at the sheriff’s office who later stopped Gorman for a
minor traffic infraction, conducted a records check, and then
proceeded to conduct a dog sniff that led to the currency. Id.
at 709–10. We held that the “investigation that followed the
second stop . . . was entirely a product of Monroe’s report—a
product that was directly and deliberately planned and
intended. The second stop was thus not an intervening
circumstance; rather, it was itself a direct result of Gorman’s
earlier unlawful detention.” Id. at 718. We emphasized that
it “misses the point to think that a second traffic infraction
and stop automatically legitimate a subsequent search when
that search was conducted pursuant to information obtained
during a prior stop.” Id. at 718–19 (internal quotation marks
omitted).

    As in Gorman, MCSO engaged in a similar type of
“gamesmanship” where it “alerted a separate law
enforcement agency,” i.e., ICE, with information that then
“significantly directed” ICE’s investigation. Id. at 716–17,
719. Like the second stop and search in Gorman, the ICE
investigation was sufficiently connected to MCSO’s initial
unlawful conduct even though it was otherwise lawful. See
id. at 718. “The [ICE investigation] was thus not an
            FRIMMEL MGMT. V. UNITED STATES                  19

intervening circumstance; rather, it was itself a direct result
of [MCSO’s] earlier unlawful [search].” Id. Based on
MCSO’s communication to ICE and publicizing of the raid,
the ICE investigation was precisely what MCSO intended.
We therefore hold that it cannot constitute an “intervening
circumstance” under Gorman.

    We also note that this case is different from Utah v.
Strieff, where the Court found that the existence of “a wholly
unconnected” and valid arrest warrant that “pre-dated” the
illegal stop was an intervening circumstance because it had
no causal connection to the earlier unlawful stop. 136 S. Ct.
at 2059, 2062–63. Unlike the arrest warrant in Strieff, the
ICE investigation was indeed connected to MCSO’s illegal
raid. And under the third and most important attenuation
factor—as discussed below—the officer in Strieff, unlike
MCSO, “was at most negligent.” Id. at 2063.

       4. Flagrancy

    Flagrancy of the Fourth Amendment violation is
“particularly significant,” especially when officers commit
the illegal search with the subjective purpose of seeking
evidence of the sort at issue. Strieff, 136 S. Ct. at 2062
(internal quotation marks omitted); see also United States. v.
Ceccolini, 435 U.S. 268, 279–80 (1978) (giving weight to the
government’s showing that the officers did not conduct the
illegal search with the intent of locating the evidence at
issue). Derivative evidence is therefore more likely to be
tainted if there is evidence that “the illegal conduct that
preceded it involved ‘either purposeful extraction of evidence
or flagrant illegality.’” United States v. Shelter, 665 F.3d
1150, 1160 (9th Cir. 2011) (quoting United States v.
Washington, 387 F.3d 1060, 1075 n.17 (9th Cir. 2004)).
20          FRIMMEL MGMT. V. UNITED STATES

    MCSO’s conduct easily meets the flagrancy standard. As
we discussed above, MCSO omitted significant and material
information and distorted facts in the affidavits, making its
conduct an egregious Fourth Amendment violation. MCSO
also materially falsified another affidavit to support another
warrant for the arrest of Bret Frimmel and the co-owner of
Frimmel Management, suggesting that MCSO repeatedly
engages in egregious Fourth Amendment violations. And as
we detail further below, MCSO’s conduct involved
“purposeful extraction” for ICE’s enforcement purposes. Id.
We thus conclude that the third attenuation factor weighs
heavily in favor of Frimmel.

III.   MCSO Had Immigration Enforcement in Its
       “Zone Of Primary Interest”

    As a final step in our exclusionary rule analysis, we must
determine whether MCSO, a separate law enforcement
agency, would be deterred from future unlawful conduct if
the evidence in the OCAHO proceedings were suppressed.
United States v. Janis, 428 U.S. 433, 458 (1976); United
States v. Medina, 181 F.3d 1078, 1082 (9th Cir. 1999). “The
Government may not successfully assert that the illegal act
was done by state or local officers and therefore the
[evidence] subsequently [obtained] [is] admissible in a [civil
proceeding], without concern as to the method by which they
were obtained.” United States v. Perez-Castro, 606 F.2d 251,
253 (9th Cir. 1979) (citing Elkins v. United States, 364 U.S.
206, 223 (1960)).

   The crux of our inquiry is whether MCSO had within its
“zone of primary interest” the later ICE investigation and
OCAHO proceedings, such that the suppression of ICE’s
            FRIMMEL MGMT. V. UNITED STATES                 21

evidence in this case would have deterrent effect on MCSO.
Janis, 428 U.S. at 458. As the Second Circuit has explained:

       in order to decide whether application of the
       exclusionary sanction is likely to have a
       significant deterrent effect, the key question is
       whether the particular challenged use of the
       evidence is one that the seizing officials were
       likely to have had an interest in at the time –
       whether it was within their predictable
       contemplation and, if so, whether it was likely
       to have motivated them.

Tirado v. C.I.R., 689 F.2d 307, 311 (2d Cir. 1982). We have
held that the zone of primary interest test is satisfied where
there the agency conducting the illegal search had a
“preexisting agreement—either implicit or explicit”—to share
information with a second agency. Grimes v. C.I.R., 82 F.3d
286, 290 (9th Cir. 1996). But an agreement is not required.
Where, as here, the law enforcement agency conducting the
unlawful search both has a policy of sharing information with
another law enforcement agency and shares the information
for the purpose of spurring the second agency to initiate an
investigation and enforcement action, the latter enforcement
action falls within the initial agency’s zone of primary
interest.

    Here, we cannot say whether there was an actual
agreement—explicit or implicit—between the MCSO and
ICE. There may well have been, but the ALJ’s discovery
rulings prevented Frimmel from developing that evidence.
The record nonetheless shows that the MCSO had a policy of
sharing information with ICE, and the only reasonable
inference is that MCSO shared this information for the
22          FRIMMEL MGMT. V. UNITED STATES

purposes of spurring ICE enforcement action. The record
shows that the day after MCSO’s raid, MCSO sent three ICE
agents an e-mail with the Shift Summary of the raid,
including the names of employees arrested for alleged
identity theft. As the ALJ noted, “[ICE] Auditor Miller also
received an MCSO Shift Summary in January 2014,
describing the arrests of Mr. Frimmel and Uncle Sam’s
general manager, Lisa Norton, for violating Arizona’s
identity theft laws.” We thus hold that the exclusionary rule
would serve to deter MCSO from Fourth Amendment
violations “by the probability that illegally obtained evidence
will not be useful to [ICE], even in a civil proceeding.” Id.

                       CONCLUSION

    For the reasons set forth above, we GRANT the petition
for review, REVERSE the ALJ’s ruling that ICE’s evidence
should not be suppressed pursuant to the exclusionary rule,
VACATE the judgment, and REMAND for further
proceedings.