Document ID: s3://data.kl3m.ai/documents/govinfo/USCOURTS/USCOURTS-ca7-14-01003/USCOURTS-ca7-14-01003-0/pdf.json

Parties Involved:
Frank Caira
Appellant
United States of America
Appellee

Document Text:

In the 

United States Court of Appeals 

For the Seventh Circuit ____________________

No. 14‐1003

UNITED STATES OF AMERICA,

Plaintiff‐Appellee,

v.

FRANK CAIRA,

Defendant‐Appellant.

____________________

Appeal from the United States District Court  

for the Northern District of Illinois, Eastern Division.

No. 08 CR 1052‐1 — Rebecca R. Pallmeyer, Judge.

____________________

ARGUED FEBRUARY 11, 2016 — DECIDED AUGUST 17, 2016

____________________

Before RIPPLE, KANNE, and WILLIAMS, Circuit Judges.

WILLIAMS, Circuit Judge. Someone used the email address

gslabs@hotmail.com to contact a Vietnamese website in an at‐

tempt to buy sassafras oil—a chemical that can be used to

make the illegal drug known as ecstasy. The website was be‐

ing monitored by the Drug Enforcement Administration,

which began an investigation that culminated in Frank Caira

Case: 14-1003 Document: 79 Filed: 08/17/2016 Pages: 12
2   No. 14‐1003

being convicted on drug charges. A key step in the investiga‐

tion was learning that Caira was the person behind the

gslabs@hotmail.com address. The DEA made that discovery

by issuing administrative subpoenas to technology compa‐

nies, without getting a warrant. Arguing that the DEA con‐

ducted an “unreasonable search” in violation of the Fourth

Amendment, Caira moved to suppress much of the evidence

against him. The district court denied his motion and we af‐

firm. Because Caira voluntarily shared the relevant infor‐

mation with technology companies, he did not have a reason‐

able expectation of privacy in the information, so his Fourth

Amendment rights were not violated.  

In sentencing Caira, the district judge erred by imposing

conditions of supervised release without justifying them on

the record. But Caira is serving a life sentence for another con‐

viction. He is not expected to be released from prison so the

conditions are not expected to be imposed. If he is released, a

court can modify the conditions at that point. So the judge’s

error was harmless and we affirm Caira’s sentence as well.

I. BACKGROUND

Between July and September 2008, emails were sent from

gslabs@hotmail.com to an email address associated with a

website hosted in Vietnam. The emails asked about buying

sassafras oil, an ingredient in ecstasy. The DEA, which had

been monitoring the website, sent an administrative sub‐

poena to Microsoft Corporation (the owner of Hotmail, the

web‐based email service for @hotmail.com email addresses).

The subpoena asked for:

[A]ll basic subscriber information, including the

subscriber’s name, address, length of service

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No. 14‐1003 3

(including start date) and types of services used

including any temporarily assigned network

address, Passport.net accounts, means and

source of payment (including credit card or

bank account number), and the account login

histories (IP Login history) of, the following

email account(s): gslabs@hotmail.com.

For this case, the request for “account login histories (IP

Login history)” is key. Internet Protocol (abbreviated as “I.P.”)

addresses are used to identify computers connected to the in‐

ternet. The allocation of addresses is centrally managed so

one can look up in a public registry which internet service

provider “owns” a particular address.

Responding to the subpoena, Microsoft gave the DEA in‐

formation about instances in which the gslabs@hotmail.com

account was accessed between July 5 and September 15, 2008.

For each instance, Microsoft provided the date, time, and an

I.P. address associated with the computer that accessed the ac‐

count. The DEA saw that 24.15.180.222 was an I.P. address fre‐

quently used to access the account, so it sent an administrative

subpoena to Comcast Corporation (the owner of that I.P. ad‐

dress). The subpoena asked for:

Any and all e‐mail addresses associated with

[24.15.180.222]; a) customer name and other

user name(s); b) addresses; c) records of session

times and durations; d) length of service (in‐

cluding start date) and types of service used; e)

telephone or instrument number or other sub‐

scriber number or identity, including any tem‐

porarily assigned network address; and f)

means and source of payment for such service

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4   No. 14‐1003

(including any credit card or bank account

numbers).

Comcast responded that the address was assigned to

Anna Caira, and Comcast gave the DEA Anna’s home ad‐

dress. The investigation continued from there and culminated

in Anna’s husband, Frank Caira, being charged with pos‐

sessing and conspiring to manufacture illegal drugs, in viola‐

tion of 21 U.S.C. sections 841(a)(1) and 846.

Caira moved to suppress evidence obtained through the

subpoenas, arguing that the government’s inquiry was a

“search” under the Fourth Amendment, and that a warrant

was required. The district court denied that motion and Caira

pleaded guilty while reserving his right to appeal the denial

of his suppression motion. This is that appeal. Caira also ap‐

peals his sentence because the district judge imposed condi‐

tions of supervised release without justifying the conditions

on the record.

II. ANALYSIS

A. Caira Did Not Have a Reasonable Expectation of Pri‐

vacy in His I.P. Addresses

The Fourth Amendment provides that “[t]he right of the

people to be secure in their persons, houses, papers, and ef‐

fects, against unreasonable searches and seizures, shall not be

violated.” U.S. Const. amend. IV. Caira contends that the

DEA’s actions amounted to an unreasonable search. The dis‐

trict court disagreed. We review the court’s legal conclusions

de novo, as well as its treatment of mixed questions of law

and fact; we review its factual findings for clear error. United

States v. Henderson, 748 F.3d 788, 790 (7th Cir. 2014).

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No. 14‐1003 5

Under the Fourth Amendment, a “search” occurs when

“the government violates a subjective expectation of privacy

that society recognizes as reasonable.” Kyllo v. United States,

533 U.S. 27, 33 (2001); see Katz v. United States, 389 U.S. 347, 361

(1967) (Harlan, J., concurring). Caira argues that I.P. addresses

reveal information about a computer user’s physical location,

and people have both a subjective and objectively reasonable

expectation of privacy in their physical location. But in United

States v. Miller, 425 U.S. 435 (1976), and Smith v. Maryland, 442

U.S. 735 (1979), the Supreme Court developed a bright‐line

application of the reasonable‐expectation‐of‐privacy test that

is relevant here. In what has come to be known as the “third‐

party doctrine,” the Court held that “a person has no legiti‐

mate expectation of privacy in information he voluntarily

turns over to third parties ... even if the information is re‐

vealed on the assumption that it will be used only for a limited

purpose and the confidence placed in the third party will not

be betrayed.” Smith, 442 U.S. at 743–44 (citing Miller, 425 U.S.

at 442–44).  

In Miller, the defendant had no reasonable expectation of

privacy in his banking records, even though they contained

sensitive financial information, because he had voluntarily

shared the information with a third party—the bank. 425 U.S.

at 442–44. And in Smith, the defendant had no reasonable ex‐

pectation of privacy in the phone numbers he dialed from his

home phone because, as a necessary step in placing phone

calls, he shared that information with the phone company. 442

U.S. at 743–44. Even if such defendants had a subjective expec‐

tation of privacy, Miller and Smith held that once information

is voluntarily disclosed to a third party, any such expectation

is “not one that society is prepared to recognize as reasona‐

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6   No. 14‐1003

ble.” Smith, 442 U.S. at 743 (internal quotation marks and ci‐

tation omitted). Accordingly, the government’s pursuit of the

information “was not a ‘search,’ and no warrant was re‐

quired.” Smith, 442 U.S. at 746.

Caira complains about the DEA’s inquiry into the I.P. ad‐

dresses that were used to access gslabs@hotmail.com. In

United States v. Weast, the Fifth Circuit wrote that I.P. ad‐

dresses are broadcast “far and wide in the course of normal

internet use.” 811 F.3d 743, 747 (5th Cir. 2016). Caira has not

argued that such a description is inaccurate; indeed, his law‐

yer appeared to concede as much at oral argument. In any

event Miller and Smith control if Caira shared his I.P. address

with even one third party. See, e.g., United States v. Christie, 624

F.3d 558, 573–74 (3rd Cir. 2010) (because defendant shared his

I.P. address with the websites he visited, the government did

not need a warrant to obtain that address through the admin‐

istrator of one of those websites); United States v. Beckett, 369

F. App’x 52, 56 (11th Cir. 2010) (nonprecedential) (defendant

did not have a reasonable expectation of privacy in his I.P. ad‐

dress because that information is “transmitted during internet

usage” and is “necessary for the [internet service providers]

... to perform their services”); United States v. Perrine, 518 F.3d

1196, 1204–05 (10th Cir. 2008) (defendant had no “Fourth

Amendment privacy expectation” in his I.P. address, which

he had shared with Yahoo! by using an online chat service);

United States v. Forrester, 512 F.3d 500, 510 (9th Cir. 2008) (de‐

fendant had no reasonable expectation of privacy in the I.P.

addresses of websites he visited, because he voluntarily

shared that information with his internet service provider, as

was necessary to view the websites).

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No. 14‐1003 7

Here, Caira shared his I.P. address with a third party—Mi‐

crosoft. When he used his home computer and sent his

username and password to Microsoft, he expected to see his

Hotmail inbox displayed on his home computer screen. It

would have done him no good if his inbox was instead dis‐

played on the screen attached to his computer at work, or a

computer at the public library, or the computer he used years

earlier when first signing up for a Hotmail account. So every

time he logged in, he sent Microsoft his I.P. address, specifi‐

cally so that Microsoft could send back information to be dis‐

played where Caira was physically present. So this case is

controlled by Miller and Smith. See Smith, 442 U.S. at 742 (“All

telephone users realize that they must ‘convey’ phone num‐

bers to the telephone company, since it is through telephone

company switching equipment that their calls are com‐

pleted.”);see also United States v. Graham, 2016 U.S. App. LEXIS

9797, at *21 (4th Cir. May 31, 2016) (en banc) (“[L]ike the de‐

fendant in Smith, 442 U.S. at 745, Defendants here did ‘assume

the risk’ that the phone company would make a record of the

information necessary to accomplish the very tasks they paid

the phone company to perform. They cannot now protest that

providing this essential information was involuntary.”).

This case parallels the Tenth Circuit’s case in United States

v. Perrine, 518 F.3d 1196. Here, law enforcement observed a

suspicious conversation on Microsoft’s email service. In Per‐

rine, it was Yahoo!’s online chat service. Id. at 1199–1201. Here,

the government sent a subpoena asking Microsoft for I.P. ad‐

dresses associated with gslabs@hotmail.com. In Perrine, the

subpoena asked Yahoo! for addresses associated with the

username “stevedragonslayer.” Id. at 1199. In each case, offi‐

cials studied the subpoena response, focused on a particular

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I.P. address, and sent a second subpoena, to the internet ser‐

vice provider that owned the address of interest (here, Com‐

cast; in Perrine, Cox Communications). In each case, the re‐

sponse to that second subpoena led to the defendant’s resi‐

dence, which led to criminal charges against the defendant.

See Perrine, 518 F.3d at 1199–1200. The Perrine court held that

Perrine had no “Fourth Amendment privacy expectation” in

the “information he gave to Yahoo! and Cox.” Id. at 1204. A

parallel conclusion here would require us to affirm the denial

of Caira’s motion to suppress.  

But Caira urges reversal, arguing that his case is special

because the DEA discovered the I.P. address associated with

his home—and the DEA knew that would happen, because

people often check their email from home—and the home is

given special protection under the Fourth Amendment, see

Payton v. New York, 445 U.S. 573, 586 (1986); Kyllo, 533 U.S. at

40. That argument is foreclosed by Smith, in which govern‐

ment officials sought information that they knew was con‐

nected to the defendant’s home, and in which the Court ex‐

plicitly rejected an argument identical to Caira’s:  

Petitioner argues, however, that, whatever the

expectations of telephone users in general, he

demonstrated an expectation of privacy by his

own conduct here, since he used the telephone

in his house to the exclusion of all others. But the

site of the call is immaterial for purposes of anal‐

ysis in this case. Although petitioner’s conduct

may have been calculated to keep the contents of

his conversation private, his conduct was not

and could not have been calculated to preserve

the privacy of the number he dialed. Regardless

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No. 14‐1003 9

of his location, petitioner had to convey that

number to the telephone company in precisely

the same way if he wished to complete his call.

The fact that he dialed the number on his home

phone rather than on some other phone could

make no conceivable difference, nor could any

subscriber rationally think that it would.  

442 U.S. at 743 (internal citations, quotation marks, and brack‐

ets omitted; emphasis in original).

Citing United States v. Jones, 132 S. Ct. 945 (2012), Caira next

argues that his case is special because of the sheer volume of

information collected by the DEA. In Jones, the Court held that

“the attachment of a Global‐Positioning‐System (GPS) track‐

ing device to an individual’s vehicle, and subsequent use of

that device to monitor the vehicle’s movements on public

streets,” constituted a Fourth Amendment search. Id. at 948.

Justice Scalia’s lead opinion applied a framework that is not

relevant here, id. at 949–54, but the concurring opinions ad‐

dressed the relevant reasonable‐expectation‐of‐privacy issue.

Traditionally, a person had no reasonable expectation of pri‐

vacy in his movements on public streets, so it would not be a

“search” if officers watched him. Id. at 953 (citing United States

v. Knotts, 460 U.S. 276, 281 (1983); Kyllo, 533 U.S. at 31–32). But

two concurring opinions, signed by five Justices total, ex‐

pressed the view that technology has changed the constitu‐

tional calculus by dramatically increasing the amount and

precision of data that the government can easily collect. Id. at

955–56 (Sotomayor, J., concurring); 964 (Alito, J., concurring).

Jones concerned GPS tracking technology, which is not at

issue here. Nonetheless, Caira argues that “the government

was essentially given data that was equivalent to placing a

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tracking device” on him. That is unhelpful exaggeration. In

concluding that “longer term” use of GPS technology consti‐

tutes a Fourth Amendment search, id. at 955, 964, the Jones

concurrences noted that such technology can monitor “every

single movement,” id. at 964, and so can reveal “trips to the

psychiatrist, the plastic surgeon, the abortion clinic, the AIDS

treatment center, the strip club, the criminal defense attorney,

the by‐the‐hour motel, the union meeting, the mosque, syna‐

gogue or church, the gay bar and on and on,” id. at 955 (quot‐

ing People v. Weaver, 12 N.Y.3d 433, 441–442 (N.Y. 2009)). But

here, the government only received records of the I.P. ad‐

dresses Caira used to log in to his Hotmail account. He did so

from two unsurprising places: home and work. The govern‐

ment received no information about how he got from home to

work, how long he stayed at either place, or where he was

when he was not at home or work. On days when he did not

log in, the government had no idea where he was. Plainly, the

government had no “tracking device.”

More fundamentally, Jones did not do away with the third‐

party doctrine. It had no occasion to, because the government

used its own GPS device to track Jones’s location—he had not

shared his location with any third party. Caira criticizes the

third‐party doctrine and he is by no means alone in that criti‐

cism. Justice Sotomayor wrote that the doctrine “is ill suited

to the digital age, in which people reveal a great deal of infor‐

mation about themselves to third parties in the course of car‐

rying out mundane tasks.” Id. at 957; see also Graham, 2016 U.S.

App. LEXIS 9797 at*39 (“[A]lthough the Court formulated the

third‐party doctrine as an articulation of the reasonable‐ex‐

pectation‐of‐privacy inquiry, it increasingly feels like an ex‐

ception. A per se rule that it is unreasonable to expect privacy

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No. 14‐1003 11

in information voluntarily disclosed to third parties seems un‐

moored from current understandings of privacy.”).  

The critique advanced by Caira, Justice Sotomayor, and

others, is not new. It was made in both Miller and Smith—in

dissent. Miller, 425 U.S. at 451 (Brennan, J., dissenting); Smith,

442 U.S. at 750 (Marshall, J., dissenting). So it is true that at

least one Justice believes “it may be necessary” to reconsider

the third‐party doctrine. Jones, 132 S. Ct. at 957 (Sotomayor, J.,

concurring). But it is also true that “[t]he Supreme Court has

... twice rejected [Caira’s critique]. Until the Court says other‐

wise, these holdings bind us.” Graham, 2016 U.S. App. LEXIS

9797 at*27. Because Caira voluntarily shared his I.P. addresses

with Microsoft, he had no reasonable expectation of privacy

in those addresses. So the DEA committed no Fourth Amend‐

ment “search” when it subpoenaed that information, and the

district court was right to deny Caira’s motion to suppress.

B. Supervised Release Error Was Harmless

Caira also appealed his sentence. The district judge sen‐

tenced him to twenty‐five years in prison, followed by five

years of supervised release. The judgment specified fourteen

conditions of supervised release, but those conditions were

not justified on the record at Caira’s sentencing hearing. Ordi‐

narily, that would require us to remand for resentencing. See

United States v. Thompson, 777 F.3d 368 (7th Cir. 2015); United

States v. Kappes, 782 F.3d 828 (7th Cir. 2015); United States v.

Johnson, 765 F.3d 702, 710–11 (7th Cir. 2014).

But Caira’s case has a wrinkle. Before pleading guilty, in

an attempt to avoid conviction, he tried to have the prosecutor

and DEA agent murdered. For that, he was sentenced to life

in prison. See United States v. Caira, 737 F.3d 455 (7th Cir. 2013).

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12   No. 14‐1003

Citing United States v. Bour, 804 F.3d 880, 887–88 (7th Cir.

2015), the government argues that the district judge’s failure

to justify the conditions of supervised release on the record

was harmless because: (i) Caira will not be released from

prison so he will not be subject to the conditions; and (ii) if for

some reason he is released one day, a court can modify the

conditions at that point, see 18 U.S.C. § 3583(e)(2). The govern‐

ment argues that such an approach is preferable because it

avoids “perpetuating expensive and time‐consuming appeals

and resentencings.” Id. at 888 (citing United States v. Silvious,

512 F.3d 364, 371 (7th Cir. 2008); United States v. Tejeda, 476 F.3d

471, 475 (7th Cir. 2007)). Caira did not respond to that argu‐

ment in his reply brief, and we find it persuasive.

III. CONCLUSION

We AFFIRM the judgment of the district court.

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