FOR PUBLICATION

UNITED STATES COURT OF APPEALS

FOR THE NINTH CIRCUIT

FRIMMEL MANAGEMENT,

LLC,

Petitioner,

v.

UNITED STATES OF AMERICA;

U.S. DEPARTMENT OF

HOMELAND SECURITY;

IMMIGRATION AND CUSTOMS

ENFORCEMENT,

Respondents.

No. 16-73906

DHS-1

OCAHO Case No.

15A00073

OPINION

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 consideringwhether 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 therewere 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

AssistantAttorneyGeneral; 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 CountySuperior 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 LopezMendoza 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 orReckless 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 whetherwhat

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

actuallywithheld 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 conductwas

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.” LopezRodriguez, 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 emailed 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 mayhave purged

[ICE’s evidence] of taint from the illegal search.” 

$186,416.00 in U.S. Currency, 590 F.3d at 951 (citingBrown,

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 easilymeets 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

“preexistingagreement—eitherimplicit 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.