The New York Times Deals blog reports on a fascinating new computer search and seizure decision, and one that I think was very likely wrongly decided:
Federal prosecutors hit another setback on Monday in their criminal fraud case against two former Bear Stearns hedge fund managers, Ralph Cioffi and Matthew Tannin, after the trial judge in Brooklyn prevented jurors from seeing an e-mail in which Mr. Tannin writes, “We could blow up.”
The e-mail, which was sent from Mr. Tannin’s personal Gmail account, was written in November 2006, months before the two hedge funds that he and Mr. Cioffi oversaw collapsed amid the subprime mortgage crisis. “I became very worried very quickly,” Mr. Tannin wrote in his e-mail. “Credit is only deteriorating. I was worried that this would all end badly and that I would have to look for work.”
Federal prosecutors in the Eastern District of New York had planned to use the e-mail to show Mr. Tannin was privately expressing doubt about the funds’ performance, but was telling his investors another story.
The opinion, United States v. Cioffi, holds that the warrant was unconstitutionally overbroad and that neither the good faith exception nor inevitable discovery exception applied so that the evidence should be suppressed. My own view is that the overbreadth holding is likely right but that the good faith analysis is wrong, and that as a result the decision to suppress the evidence was incorrect.
First, the facts. The government suspected that a personal G-Mail account contained evidence of a massive fraud scheme. The affidavit fully explained the reasons for that belief in the affidavit, and asked for permission to get the warrants that related to the fraud offense. The actual warrant itself was phrased in broader language, however: It gave the agents permission to obtain “all e-mail” in the G-Mail account “up through August 12, 2007,” a date that the suspect hired an attorney (the limitation being imposed to avoid potentially obtaining attorney-client communications). The agents sent the warrant to Google, and Google responded with a CD-ROM containing the e-mails. The government then looked through the e-mails and quickly found an incriminating e-mail the suspect had sent to himself in which he seems to have detailed his own fraud activities as sort of a diary entry.
Judge Block held that the e-mail could not be admitted under the Fourth Amendment. The government conceded that the e-mails were protected by the Fourth Amendment, and applying that standard the warrant violated the particularity requirement by asking for “all e-mails” in the time window rather than just the e-mails involving fraud. While the affidavit did limit the case to e-mails looking for fraud, and the agents only looked for fraud (and certainly the e-mail in question was such a fraud e-mail), the warrant itself was not particular enough because the warrant itself did not contain the limitation and it was not fully and adequately incorporated into the affidavit. Further, the good faith exception did not apply because the agents should have known that the warrant was insufficient.
I have mixed views of the court’s opinion, but I think the ultimate decision to suppress is incorrect. I think the basic holding that the Fourth Amendment requires agents to give some guidance as to which e-mails it wants rather than to seize the entire account is probably correct. The caselaw is very sparse here, but courts have required the government to be more specific in the case of seizing a computer hard drive. When the government gets a warrant to search for and seize digital evidence at home, the government can’t get a warrant for “all computers,” but rather must ask for “all computers that contain child pornography” or “all records of a conspiracy to commit wire fraud stored in a computer.” See, e.g., United States v. Riccardi, 405 F.3d 852 (10th Cir. 2005) (McConnell, J.). E-mail accounts today are big enough that the same rule should probably apply to individual e-mail accounts that applies to individual computers: There must be some guidance, even if only very general guidance, as to what the agents are to look for when they have the CD-ROM and start to look through it. A date restriction helps but probably isn’t enough, assuming that there are lots of e-mails before that date. So, assuming that the affidavit wasn’t sufficiently incorporated — a question I’ll leave to the side because the standards among the circuits tends to vary, and it’s a very technical issue — I think the basic Fourth Amendment holding was likely right.
On the other hand, I think the good faith exception should apply, and Judge Block was therefore wrong to suppress the evidence. The question is whether the constitutional error was so clear that a reasonable agent would realize the warrant violated the Fourth Amendment. I don’t think that standard is satisfied for two primary reasons:
First, no district court in the Circuit or the Second Circuit itself has ever held that e-mail is protected by the Fourth Amendment, and the federal Stored Communications Act, 18 U.S.C. 2703(b), takes the position that no warrant is required to obtain e-mails, such as the ones here, that are older than 180 days. As regular readers may know, I argue in a forthcoming article that such e-mail should be protected by a warrant requirement. And it so happens in this case that the government conceded in this case that e-mail is protected by a warrant requirement (presumably because they obatined a warrant — no need to fight that battle in this case). But I don’t think a reasonable police officer would necessarily know that a valid warrant was required and that the relevant federal statute governing e-mail is unconstitutional.
Indeed, there is a remarkable irony in the court’s ruling. If the government had just subpoenaed all the e-mails and not obtained a warrant, as 18 U.S.C. 2703(b) permits, the good faith exception would have applied because the agents could have reasonably claimed good faith reliance on the statute. See, e.g., United States v. Ferguson, 508 F. Supp. 2d 7 (D.D.C. 2007) (accepting such an argument). The agents apparently decided to be more cautious and to get a warrant anyway, even though the federal statute does not require it. But Judge Block ends up punishing the government for providing more process rather than relying on the statute: He ruled that the agents can’t rely on the good faith exception because they obtained a warrant but didn’t meet the far more strict particularity requirements of warrants. That’s an odd result.
The second reason I think the good faith exception applies is that the court’s ruling is directly contrary to the most relevant precedent, United States v. Lamb, 945 F. Supp. 441 (N.D.N.Y. 1996), the only other decision that comes to mind on the particularity for e-mail accounts. Lamb was an early child pornography case involving a single warrant to obtain the entire contents of 78 AOL e-mail accounts. District Judge Munson held that the one warrant for the entire contents of 78 accounts was constitutional, even though the warrant asked for all e-mail and did not specify only e-mails that involved child pornography crimes:
[The warrant] seeks “all stored files in original format in individual files” and any printouts of the same. There was probable cause to believe that some of those files were image files containing the forbidden depictions. Although the language does not limit investigators to seizing image files only or image files of child pornography only, the actual content of a computer file usually cannot be determined until it is opened with the appropriate application software on a computer. The agents who were tasked to obtain account records related to seventy-eight individuals were not obligated to identify the contents of computer files on AOL’s premises. Because there was probable cause to believe that stored files in the accounts of the suspects contained evidence of the crime, viz. the depictions of child pornography themselves, the warrant properly authorized the search and seizure of these particular items.
Id. at 458–59. In a footnote, Judge Munson added: “it is unreasonable to require the executing officers to identify which files actually contain child pornography and which do not in AOL’s Virginia headquarters. That task may be more properly performed by a government computer technician at an FBI lab or office.” Id. at 458 n.10.
I tend to think Lamb is wrongly decided, or at least outdated given the incredible storage capacity of today’s G-Mail accounts as compared to 1996 America Online accounts. But it’s the only precedent I know of on particularity for e-mail accounts, and it said that a single warrant for the contents of 78 accounts with no date restrictions at all complies with the Constitution. Given Lamb, I think an officer in 2009 could reasonably believe that the warrant in this case was constitutional and that the good faith exception applies.

Splunge says:
Gosh, how clumsy modern miscreants are. If I felt it necessary to write e-mails to myself in which I thought the government might conceivably ever take an interest, I’d first pay a visit here:
http://www.gnupg.org/
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October 27, 2009, 4:00 amCleanville Tziabatz says:
Get rid of the exclusionary rule. The guy is guilty. 4a is for the innocent.
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October 27, 2009, 6:02 amgeorge weiss says:
agree w/ good faith analysis (at least as a matter of law-not sure i like the good faith rule as a matter of policy)
disagree though that it was overbroad in the first place. remember the 4th amendment’s particularity requirement requires listing not of the things searched but only of the things to be seized. The agents are certainly searching the emails here...but can you really seize an email in the manor it was done here? the agents only “seized” a copy-the defendant wasn’t deprived of access to the email during the “seizure.” This is particularly true when the warrant is served on a third party as here or when the warrant is served on someone who is well aware of what the police are looking for. As for United States v. Riccardi, 405 F.3d 852 (10th Cir. 2005) )holding seizure occurred when searching hard drive) it isn’t clear from the facts there whether there was a copying of the drive or the physical drive was taken.
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October 27, 2009, 7:42 amNickM says:
Child pornography requires an image file. There can be other emails without images with evidence of the crime (e.g., offers to purchase), but it would be very simple to limit a warrant only to those emails that contain embedded or attached images.
In a case such as this, how would the judge expect the warrant be limited yet still cover the relevant evidence? Is this to be a game of “guess the terms to search for”?
Nick
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October 27, 2009, 8:24 amMCM says:
But what about ASCII porn?
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October 27, 2009, 8:32 amWht9 says:
Terrible decision.
Think of the entirety of the gmail account as a storage trunk. The emails are letters contained in the trunk.
The know there are letters in the trunk that might contain information about criminal activity. So they get a warrant to seize the trunk. Then they search the trunk for the information.
And that analogy works better here than the judges rationale.
Google is a 3rd party. The judges rule would force google to search through the trunk to find the information. So how would the judge have google comply with his more detailed order, it seems like quite a burden to put on a third party.
If google had in its a possession a physical trunk with the information inside, couldnt the government just seize the trunk?
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October 27, 2009, 9:14 amMalvolio says:
While I agree it would be absurd to subpoena Google for “e-mails involving fraud” (how would the Google technicians possibly know?), I would like to point out that the document in question is not an email. An email goes from one person to another. The defendant in this case was using an email system as a journal. It seems to me that a journal entry should have stronger protection, on self-incrimination grounds, than an email (which of course is intended to be read by another party, who might himself be subpoenaed and compelled to disclose the contents)
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October 27, 2009, 10:51 amSnaphappy says:
“G-Mail” sounds like what the feds (i.e. “G-Men”) use to communicate.
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October 27, 2009, 11:09 amDuracomm says:
Related story
The Search for Financial Villains Founders
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October 27, 2009, 11:09 amPintler says:
As a matter of practice, it may be difficult to tell ‘email’ emails from ‘journal’ emails. I recall hearing of a case where people were communicating as follows: person A drafted an email, and saved it in a ‘Drafts’ folder. Person B logged in to the same account and viewed the same message, and updated it with his reply, and so on. No one ever hit ‘Send’. This was to avoid surveillance that was listening only for emails that were ‘sent’.
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October 27, 2009, 11:10 amOrin Kerr says:
Cleanville,
If you’d like to comment here, please stop trolling. Thanks.
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October 27, 2009, 11:22 amJay says:
Malvolio–Is there any case law that supports keeping out journals on the basis of the right not to incriminate oneself?
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October 27, 2009, 11:31 amCleanville Tziabatz says:
Now I thought that trolling was writing something that you didn’t sincerely believe for the purpose of angering others. I sincerely believe what I write here, and I don’t see why my beliefs about how the Fourth Amendment is, and how it ought to be, would anger anyone. So, to my mind, I am not trolling. My comment on this thread is an excellent example of not-trolling as I understand the concept. I call for the end of the exclusionary rule. I am not the only one to call for the end of the exclusionary rule these days. It is a real possibility. It would take care of the difficult issues noted in your post. You may not agree with my proposal for some reason, but I don’t see why you would possibly be angered by it, or why you would possibly think that I am not sincere in my proposal (just to be clear: I most certainly am sincere).
Where is the “trolling”? Is there some new definition of trolling that I am not aware of?
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October 27, 2009, 12:34 pmPatHMV says:
How could the warrant have been more particularized, in this instance? Is the government required to give Google a list of key terms, and have Google turn over only e-mails which contain those terms? Surely the government is not so limited, because some e-mails may be highly incriminating without using any word such as “fraud.” In some instances, an e-mail as simple as “yes” may be highly relevant to criminal intent, say if it is a reply to another e-mail which says “shall I destroy all the documents about the fraud?”
Is it purely a matter of semantics or process here? Should the government have appointed a “filter team,” and detailed the appointment of such team in the warrant application, in order to review all of the subject’s e-mails and only pass on to prosecutors and investigators those which the filter agents (all themselves usually FBI agents) believe are relevant to the case? That would certainly not be required in most circumstances, were we talking about physical records. If the warrant said “search for letters discussing the alleged fraud,” then the FBI search team would be legally entitled to review all letters in the office or house, while only “seizing” the relevant letters. In the computer realm here, the e-mails were really not “seized” in the traditional sense, because they remained on Google’s servers, fully accessible to the defendant, unlike a traditional seizure of records which deprives the subject of the use of the records while the government has them.
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October 27, 2009, 12:46 pmDJR says:
I’m usually all in favor of warrants, more particular warrants, and the exclusionary rule, but I too am having trouble determining how one would seize only the relevant emails. In civil litigation we have discovery, where a party can ask for “all documents related to the Bear Stearns hedge fund.” The party then has to go through a lengthy and expensive process of hiring a team of document reviewers, go review the documents, separate out those that are relevant and not privileged, and then produce them.
But warrants don’t work that way. They are executed by law enforcement, with the imprimatur of a judge saying it’s ok to rummage through all the irrelevant materials in order to get to the relevant materials. An officer looking for a knife in a house has permission to look anywhere a knife might be hidden, even if there is no knife in many of those places. An officer looking for a file is permitted to look through the entire file cabinet and anywhere else the file might be hidden. Here, officers effectively are the document reviewers, using searches or other methods to find the relevant emails among the rest of them.
Orin: How would you propose to cure what you view as the Fourth Amendment problem here? Surely the solution is not to put the burden on Google to find the relevant emails?
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October 27, 2009, 1:17 pmwolfefan says:
Hi Cleanville —
I don’t know about trolling, but at this point isn’t the guy legally innocent? Based on the OP he hasn’t been found guilty of anything. By your standard shouldn’t the Fourth Amendment apply to him?
IANAL and I’m not going to spend much time on it, but I have trouble figuring out what a rule saying “only innocent people get to use the Fourth Amendment” would look like. You say that you are sincere in your proposal, and I have no reason to doubt you, but honestly — you didn’t really make any proposal. Just a a couple of throwaway lines that taken at face value make no sense to me. Could you flesh it out a little more?
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October 27, 2009, 6:10 pmCleanville Tziabatz says:
Absolutely: (i) get rid of the exclusionary rule; and (ii) easier remedies for victims of fruitless searches and fruitless seizures.
You know how when an airline bumps you from a flight, you get a payment. You don’t have to go to court to get a payment. You don’t have to fill out extensive forms to get a payment. Rather, you GET a payment. Victims of fruitless searches and seizures should be AUTOMATICALLY entitled to this kind of payment.
Now you might be thinking that this new remedy I have dreamed up (with a little help from the airline industry) switches the perspective from which 4a “reasonableness” from an ex ante basis to a post hoc basis. If you are thinking that, then you are absolutely correct. Trying to emulate and evaluate ex ante judgement calls is a decisional process too easily manipulable (and regularly manipulated) by police.* The proof is better adjudged from the pudding. If a department finds itself making lots of fruitless searches, then they will need to tone down their act or go bankrupt. If a police department makes no searches, then they will catch no criminals. The idea is to calibrate the payements so that over the long run, FRUITFUL searches and seizures are something that happen more often than FRUITLESS searches or seizures.
My system provides a much more determinative and fair and adjustable metric than the exclusionary rule world we currently live in. Sure, it presumes a fruitless search was unreasonable. That may not be perfectly fair, but it is a lot fairer than telling someone stopped for driving while black that he can save up and hire a lawyer and maybe win a small award for the violation he suffered, unless of course the jury is racist or biased against poor people or whatever (which is the current 4a enforcement system with respect to innocent victims).
Sure, the change I am suggesting is fundamental, but no more so than Brown v. BOE or Roe v. Wade. The first step is getting rid of the exclusionary rule so that the police run roughshod over us until we are angry enough, as a society, to demand a remedy. The new remedy, whether it is my idea or some creative 4a law professor’s idea, will be sure to be fairer to innocents than the exclusionary rule driven landscape we now inhabit.
FOOTNOTE
* see, http://www.missoulian.com/news/local/article_94930e40-ba0d-11de-9fcf-001cc4c03286.html (the declaratory judgment opinion issued 15 Oct 2009 by the court in this case — deals with reasonableness of force rather than search, but the concern about the police having their way with juries applies).
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October 27, 2009, 7:24 pmwolfefan says:
Thanks, Cleanville, for your prompt and thorough response!
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October 27, 2009, 8:54 pmCleanville Tziabatz says:
Yeah, the trolling thing is drenched in bogosity. I have faith that Professor Kerr will come to his senses at least about that, if not other things. I mean, for crying out loud, I am “Cleanville Tziabatz.” How many people can say that? Very few. You know it is true.
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October 27, 2009, 9:14 pmOrin Kerr says:
Cleanville,
You have convinced me that you are not a troll under the traditional definition — I stand corrected. However, please keep your comments relevant and civil if you would like to comment here.
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October 27, 2009, 10:01 pmCleanville Tziabatz says:
Aye. Relevant is easy. Civil is harder, esp with the policemen and prosecutors about, but I understand that it is a standard I will have to meet if I want to keep my commentating privs. Sounds fair enuf.
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October 27, 2009, 10:14 pmOrin Kerr says:
Cool. See you on the interwebs.
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October 28, 2009, 1:21 amPintler says:
Suppose that getting the $25 payment for a fruitless search sounds like a good deal to me — after all, it takes me all day to get $25 panhandling. Why shouldn’t I call 911 from a pay phone and report that someone with my description is acting suspiciously, or wait until I see a police car drive by, and throw an airsoft gun into the bushes and run like heck (but not fast enough, of course, to actually escape)?
How do you propose dealing with people trying to ‘entrap’ the police into fruitless searches for profit?
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October 28, 2009, 8:28 amFormer Law Student says:
I may be way off base here, but why didn’t the prosecutor argue the “Inevitable Discovery Doctrine” or “Indepedent Source Doctrine.” If, under the SCA and prevailing case law, the police did not need a warrant to subpoena the e-mails, then couldn’t the prosecutor argue that the evidence would have been uncovered anyway?
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October 28, 2009, 9:09 amFormer Law Student says:
Whoops I stand corrected — I see, now, that the prosecutor did argue that doctrine. And I guess since the government conceded a warrant was necessary, they couldn’t also argue that the information could have been obtained legally without a warrant.
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October 28, 2009, 9:20 amJOLT Digest » U.S. v. Cioffi | Harvard Journal of Law & Technology says:
[...] overview of the case. The Eric Goldman Blog also provides a summary of the case. Orin Kerr of the Volokh Conspiracy criticizes the ruling, saying that the good faith exception should have been granted since the case [...]
Sandra Bullock says:
Good blog, but im having some minor problems with some images not showing. Maybe because i use Opera Browser? Well i’m bookmarking it for further reading.
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November 14, 2009, 6:47 pm