13‐2963‐cv(L)

Drimal v. Makol, et al.

In the

United States Court of Appeals

For the Second Circuit

________

AUGUST TERM, 2014

ARGUED: NOVEMBER 4, 2014

DECIDED: MAY 15, 2015

Nos. 13‐2963‐cv; 13‐2965‐cv

ARLENE VILLAMIA DRIMAL,

Plaintiff‐Appellee,

v.

PAULINE TAI,

Defendant,

DAVID MAKOL, JAN TRIGG, FRANK LOMONACO, DAVID J. FORD,

EDMUND ROM, KEVIN RIORDAN, ADRIAN BUSBY, BRIAN HARKINS,

JOANN MAGUIRE, MARIA A. FONT, MARTHA M. BERDOTE, THOMAS J.

D’AMICO, MARK MUNSTER, CHRISTOPHER DEGRAFF, S. MENDOZA‐

PENAHERRERA,

Defendants‐Appellants.

________

Appeal from the United States District Court

for the District of Connecticut.

No. 3:12‐cv‐0717 – Warren W. Eginton, Judge.

________

Before: WALKER, LYNCH, and CHIN, Circuit Judges,  

________
2

Arlene Villamia Drimal brought this action against sixteen FBI

agents alleging that they violated Title III of the Omnibus Crime

Control and Safe Streets Act of 1968, 18 U.S.C. §§ 2510‐2522, when

they listened to her private calls with her husband. The calls were

intercepted during an authorized wiretap on the telephone of

Drimal’s husband as part of an investigation into a conspiracy to

commit securities fraud. Defendant FBI agents moved to dismiss the

suit for failure to state a claim and on qualified immunity grounds.

The District Court for the District of Connecticut (Warren W.

Eginton, Judge) denied their motion, finding the complaint sufficient

to state a claim despite its failure to mention minimization. We hold

that Drimal’s complaint in its present form does not plausibly state a

claim because it recites only legal conclusions. We also conclude that

in its qualified immunity analysis the district court should have

assessed the reasonableness of the agents’ minimization efforts as

they relate to each defendant. Accordingly, we REVERSE the district

court’s denial of the motion to dismiss, and REMAND for the
3

district court to dismiss the complaint without prejudice to

repleading and for further proceedings consistent with this opinion.

________

JOHN R. WILLIAMS, New Haven, CT, for Plaintiff‐

Appellee.

EDWARD HIMMEL, (Barbara L. Herwig, Catherine

H. Dorsey, on the brief), for Stuart F. Delery,

Deputy Assistant Attorney General, and Deirdre

M. Daly, United States Attorney, United States

Attorney’s Office for the District of Connecticut,

for Federal Defendants‐Appellants.

JAMES I. GLASSER, Wiggin & Dana, LLP, New

Haven, CT, for Defendant‐Appellant Adrian Busby.

________

JOHN M. WALKER, JR., Circuit Judge:

Arlene Villamia Drimal brought this action against sixteen FBI

agents alleging that they violated Title III of the Omnibus Crime

Control and Safe Streets Act of 1968, 18 U.S.C. §§ 2510‐2522 (“Title

III”), when they listened to her private calls with her husband. The

calls were intercepted during an authorized wiretap on the

telephone of Drimal’s husband as part of an investigation into a

conspiracy to commit securities fraud. Defendant FBI agents moved
4

to dismiss the suit for failure to state a claim and on qualified

immunity grounds. The District Court for the District of Connecticut

(Warren W. Eginton, Judge) denied their motion, finding the

complaint sufficient to state a claim despite its failure to mention

minimization. We hold that Drimal’s complaint in its present form

does not plausibly state a claim because it recites only legal

conclusions. We also conclude that in its qualified immunity

analysis the district court should have assessed the reasonableness

of the agents’ minimization efforts as they relate to each defendant.

Accordingly, we REVERSE the district court’s denial of the motion

to dismiss, and REMAND for the district court to dismiss the

complaint without prejudice to repleading and for further

proceedings consistent with this opinion.

BACKGROUND

On May 15, 2012, Drimal filed a civil complaint against sixteen

FBI agents who had administered an authorized wiretap of her

husband’s cellular telephone, alleging that they violated Title III by
5

listening to her private conversations with her husband.1 Although

the complaint does not refer to minimization, under Section 2518(5)

of Title III, it is a violation to fail to “minimize the interception of

communications not otherwise subject to interception.” Section 2520

gives “any person whose wire, oral, or electronic communication is

intercepted, disclosed, or intentionally used in violation of this

chapter” the right to “recover from the person or entity, other than

the United States, which engaged in that violation such relief as may

be appropriate,” including damages. 18 U.S.C. § 2520(a).  

I. Mr. Drimal’s Criminal Case

Drimal’s complaint arises out of an earlier criminal

prosecution in the Southern District of New York that was

ultimately tried before Judge Richard J. Sullivan. See United States v.

Goffer, 756 F. Supp. 2d 588 (S.D.N.Y. 2011), aff’d, 721 F.3d 113 (2d Cir.

2013). The trial was preceded by a wide‐ranging federal securities

fraud investigation that included a wiretap of her husband’s cellular

 

1 Drimal also alleges that the defendants violated Section 52‐570d of

the Connecticut General Statutes. Like the district court, we focus on her

Title III claim.  
6

phone during which FBI agents intercepted and monitored his calls

with Drimal.  

A court order authorizing the wiretap of Mr. Drimal’s cellular

telephone for two thirty‐day periods in late 2007 and early 2008, id.

at 590, specified that “[m]onitoring of conversations must

immediately terminate when it is determined that the conversation

is unrelated to communications subject to interception . . . . If a

conversation is minimized, monitoring agents shall spot check to

ensure that the conversation has not turned to criminal matters.” Id.   

The Assistant United States Attorney who supervised the

wiretap also issued written instructions on the minimization

requirement. He instructed agents to “listen to the beginning of each

communication only so long as is necessary to determine the nature

of the communication and, in any case, no longer than a few minutes

unless the communication is ‘pertinent.’” Id. In addition, he advised

that “[i]f, after several days or weeks of interception” it became

apparent that conversations between Mr. Drimal and another party

involved “invariably innocent, non‐crime related matters,” then
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communications between those parties “should not be recorded,

listened to, or even spot monitored.” Id. Finally, the agents were told

to “discontinue monitoring if you discover that you are intercepting

a personal communication solely between husband and wife” unless

the conversations included a third party or addressed “ongoing as

opposed to past violations of law.” Id. at 591. During the wiretap,

agents monitored over one thousand of Mr. Drimal’s telephone

conversations, including approximately 180 calls with Mrs. Drimal

that were not pertinent to the investigation. Id. at 591, 595.

In 2010, Mr. Drimal moved before Judge Sullivan to suppress

the entire wiretap on the basis that the government had failed to

properly minimize calls with his wife. Id. at 589, 591. At the hearing,

several agents testified, including defendant Special Agent

Lomonaco who admitted that he had listened to a privileged

conversation which he had “no right” to hear and defendant Special

Agent Ford who remembered “kicking [him]self” for listening to a

privileged marital conversation. J.A. 49.

The district court denied the motion to suppress all of the
8

wiretapped phone calls. Focusing on eighteen calls it identified as

“potentially violative,” the district court stated that the monitoring

of three of these calls had been “particularly egregious,” 756 F. Supp.

2d at 594, and that another five calls “raise[d] questions about the

sufficiency of the agents’ minimization efforts,” id. at 595. The

district court concluded, however, that “on the whole, the wiretap

was professionally conducted and generally well‐executed,” id. at

597, even as it described certain failures to minimize private calls

between husband and wife as “inexcusable and disturbing,” id. at

598. The district court observed that the “most egregious failures

occurred in the early stages of the wiretap,” when agents might still

be learning to identify Drimal’s voice, and that agents minimized the

calls satisfactorily later in the wiretap. 2  Id. at 596.  

II. Mrs. Drimal’s Civil Lawsuit

Following the conclusion of her husband’s criminal case,

Drimal filed this action in the District of Connecticut against sixteen

 

2 At some unspecified point later in the wiretap, agents were apprised

of Drimal’s telephone number, which was posted at the monitoring

station.
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FBI agents who monitored or supervised the monitoring of the

wiretap, seeking compensatory and punitive damages against the

agents in their personal capacities. The district court denied the

defendants’ motion to dismiss for failure to state a claim and on

qualified immunity grounds.

Defendants now appeal from the denial of qualified

immunity.

DISCUSSION

We review de novo the denial of a motion to dismiss pursuant

to Federal Rule of Civil Procedure 12(b)(6) for failure to state a claim

upon which relief can be granted. Brown v. Daikin Am. Inc., 756 F.3d

219, 225 (2d Cir. 2014); see also Garcia v. Does, 779 F.3d 84, 91 (2d Cir.

2015). Although a district court’s denial of a motion to dismiss is not

a final judgment, we review it here because the defendants’

qualified immunity claim occasions an interlocutory appeal. See

Ashcroft v. Iqbal, 556 U.S. 662, 671‐72 (2009) (stating that decision

denying qualified immunity can be appealable order); see also

Mitchell v. Forsyth, 472 U.S. 511, 530 (1985) (holding that “a district
10

courtʹs denial of a claim of qualified immunity, to the extent that it

turns on an issue of law, is an appealable ‘final decision’ within the

meaning of 28 U.S.C. § 1291 notwithstanding the absence of a final

judgment”).

The district court’s rulings on the pleadings and on qualified

immunity suffer from two deficiencies. First, the district court erred

in finding Drimal’s complaint sufficient to plead a violation of Title

III because Drimal simply asserted in a conclusory fashion that

intercepting marital telephone calls violated Title III without any

reference to the duty to minimize. Second, in evaluating defendants’

claims of qualified immunity, the district court ruled on all the

defendants as a single group instead of evaluating Drimal’s claims

against each defendant individually.

Accordingly, we vacate the district court’s denial of the

motion to dismiss and direct the dismissal of the complaint with

leave to replead under Federal Rule of Civil Procedure 15(a)(2)

because it appears that amending the complaint would not be futile.

Cf. Panther Partners Inc. v. Ikanos Commcʹns, Inc., 347 F. Appʹx 617,
11

622 (2d Cir. 2009) (summary order) (remanding where “granting

leave to amend anew may not be futile in this case”).   

I. The Plausibility of Drimal’s Complaint

To survive a 12(b)(6) motion to dismiss, a “complaint must

contain sufficient factual matter, accepted as true, to state a claim to

relief that is plausible on its face.” Iqbal, 556 U.S. at 678 (internal

quotation marks omitted). Courts “are not bound to accept as true a

legal conclusion couched as a factual allegation.” Id. (internal

quotation marks omitted). While this standard “does not require

detailed factual allegations . . . it demands more than an unadorned,

the‐defendant‐unlawfully‐harmed‐me accusation.” Id. (internal

quotation marks omitted).  

Drimal’s complaint fails to plausibly allege a violation of law

because she recites only legal conclusions. Conspicuously absent

from the complaint is the concept of minimization. Drimal simply

alleges that each defendant “unlawfully intercepted and listened to

privileged, confidential marital communications,” identifying the

allegedly unlawfully monitored calls only by date.    J.A. 50. These
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allegations lack specificity. As drafted, they give no indication of the

circumstances that support the conclusory allegation of

unlawfulness.  

Although 18 U.S.C. § 2517(4) specifies that “[n]o otherwise

privileged wire, oral, or electronic communication intercepted in

accordance with, or in violation of, the provisions of this chapter

shall lose its privileged character,” nothing in Title III prohibits

outright the interception or monitoring of privileged conversations.

To be sure, § 2518(5) requires that such calls be “minimized” but that

requirement cannot be gleaned from the complaint.

The court order that authorized this wiretap included specific

instructions governing how conversations between husband and

wife should be treated.3 These instructions provided:  

You are to discontinue monitoring if you discover that

you are intercepting a personal communication solely

between husband and wife. If it appears that a third

person is present during this communication, however,

 

3 We take judicial notice of the court order, which is discussed in Goffer,

756 F. Supp. 2d at 590‐91, because Drimal’s complaint cites frequently to

Goffer. See Roth v. Jennings, 489 F.3d 499, 509 (2d Cir. 2007) (“Documents

that are attached to the complaint or incorporated in it by reference are

deemed part of the pleading and may be considered.”).
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the communication is not privileged. So too, if the

communication deals not with private matters between

husband and wife, but instead with ongoing as opposed

to past violations of law, it is not a privileged

conversation.  

Goffer, 756 F. Supp. 2d at 591. These instructions do not prohibit the

interception and monitoring of marital calls, but they do require

their minimization. This is entirely logical: agents obviously must

intercept and listen to a call before they can determine whether a

conversation is privileged and subject to minimization and, if so, to

what degree. Accordingly, to survive a motion to dismiss, Drimal’s

complaint must include facts alleging how each defendant failed to

comply with his or her duty to minimize specified telephone calls as

required by § 2518(5) and the authorization order.

In assessing the complaint, the district court read the

minimization requirement into the plaintiff’s allegations that

defendants “unlawfully” listened to her calls and required no

greater specificity as to the facts alleged. However, a simple

allegation that defendants behaved “unlawfully,” unsupported by

any factual detail, is precisely the type of legal conclusion that a
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court is not bound to accept as true on a motion to dismiss, and the

district court erred in doing so here.

II. The Defendants’ Claim of Qualified Immunity

In the event that plaintiff files an amended complaint

following remand that rectifies the deficiencies we have outlined,

the district court must focus more closely on the claims of qualified

immunity as they relate to each defendant. We think it useful here to

suggest some guidance in this regard.

Qualified immunity shields government officials “from

liability for civil damages insofar as their conduct does not violate

clearly established statutory or constitutional rights of which a

reasonable person would have known.” Harlow v. Fitzgerald, 457 U.S.

800, 818 (1982). It “provides ample protection to all but the plainly

incompetent or those who knowingly violate the law.” Malley v.

Briggs, 475 U.S. 335, 341 (1986). To lose immunity, an official must

violate a right, the contours of which are “sufficiently clear that a

reasonable official would understand that what he is doing violates

that right.” Anderson v. Creighton, 483 U.S. 635, 640 (1987).  
15

The Supreme Court has “repeatedly stressed the importance

of resolving immunity questions at the earliest possible stage [of the]

litigation.” Wood v. Moss, 134 S. Ct. 2056, 2065 n.4 (2014) (internal

quotation marks omitted). “Because qualified immunity is an

immunity from suit rather than a mere defense to liability[,] it is

effectively lost if a case is erroneously permitted to go to trial.”

Pearson v. Callahan, 555 U.S. 223, 231 (2009) (internal quotation marks

and ellipsis omitted). While issues related to qualified immunity

frequently must await a motion for summary judgment, that might

not be the case here. A putative amended complaint, pleaded with

the requisite specificity based on the hearing before Judge Sullivan,

likely would enable the district court to address qualified immunity

issues, at least in part, at the pleading stage.

Section 2518(5) of Title III does not precisely define the

minimization requirement. It states only that agents must “minimize

the interception of communications not otherwise subject to

interception.” 18 U.S.C. § 2518(5). In Scott v. United States, the

Supreme Court articulated an “objective reasonableness” test to
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determine whether agents have properly minimized calls. 436 U.S.

128, 138 (1978). This standard requires “an objective assessment of

an officerʹs actions in light of the facts and circumstances then

known to him.” Id. at 137.

The district court must thus evaluate each agent’s

minimization efforts under such an “objective reasonableness”

standard based on the facts of this case to determine whether each

defendant “would understand that what he is doing violates” Title

III’s minimization requirement. Anderson, 483 U.S. at 640.

The government argues on behalf of all but one defendant4

that a per se “two‐minute rule” derived from United States v.

Bynum—treating calls monitored for less than two minutes as

properly minimized—entitles agents to immunity for interceptions

that did not exceed that duration. 485 F.2d 490 (2d Cir. 1973), vacated

and remanded on other grounds, 417 U.S. 903 (1974). In Bynum, we held

that a wiretap that monitored 2,058 calls in a vast narcotics

conspiracy case did not violate Title III’s minimization requirement.

 

4 The appellate staff of the Department of Justice’s Civil Division

submitted the brief for all defendants except Special Agent Adrian Busby.
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Id. at 500‐02. We excluded calls under two minutes from our

evaluation of the wiretap, noting that “in a case of such wide‐

ranging criminal activity as this, it would be too brief a period for an

eavesdropper even with experience to identify the caller and

characterize the conversation as merely social or possibly tainted.”

Id. at 500.

While our reasoning in Bynum, which didn’t pertain to any

privileged communications, can be read to suggest a presumption

that calls less than two minutes long need not be minimized, this is

not a fixed rule for every case: whether the two‐minute presumption

applies is a fact‐specific determination.

This case does not present the same circumstances as Bynum.

Many of the violations here took place in the early stages of the

wiretap when defendants were less familiar with the case and with

Mrs. Drimal’s lack of involvement in it, but the agents should have

realized reasonably early in the wiretap that these husband and wife

conversations were not relevant to the investigation. As Judge

Sullivan noted in Goffer, Mr. and Mrs. Drimal occasionally discussed
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“deeply personal and intimate” issues, 756 F. Supp. 2d at 594, and

“in each of these calls it should have been apparent within seconds

that the conversation was privileged and non‐pertinent,” id. at 595.

As a result, the reasoning from Bynum that it would be too difficult

to minimize calls under two minutes is not applicable here where

agents could determine in seconds that the calls between husband

and wife were entirely personal in nature. The two‐minute

presumption we applied in Bynum thus does not automatically

shield defendants against the failures to minimize calls under two

minutes that the putative amended complaint is likely to allege.

Should Drimal file an amended complaint, in assessing the

defendants’ claim of qualified immunity on remand, the district

court must consider the actions of each individual defendant. Cf. Gill

v. Monroe Cnty. Depʹt of Soc. Servs., 547 F.2d 31, 32 (2d Cir. 1976)

(remanding for district court to consider “each plaintiff, each cause

of action and each defendant”).  Government Exhibit 30, featured at

the suppression hearing in the criminal case and of which we take
19

judicial notice,5 makes it apparent that different defendants

responded differently to their duty to minimize: some may be able

to successfully claim qualified immunity even at the pleading stage

where others may not.6

CONCLUSION

For the reasons stated above, we REVERSE the district court’s

denial of defendants’ motions to dismiss, and REMAND for the

district court to dismiss the complaint without prejudice to

repleading and for further proceedings consistent with this opinion.

 

5 See supra Note 2.

6 Without addressing the merits of a qualified immunity claim by any

particular defendant, it is worth noting that the conduct of the agents in

question covers a broad range. Three named defendants, two of whom

gave testimony that could be read as acknowledging that they listened to

conversations they knew they should not have, accounted for the eight

conversations whose recording most troubled Judge Sullivan. At the other

extreme, it is difficult to review Government Exhibit 30 without

concluding that at least some of the named defendants seem to have been

quite exemplary in their minimization practices. Other factors, such as the

stage of the wiretap at which the calls were intercepted and the nature and

timing of minimization supervision, may well be relevant to the qualified

immunity analysis.