New York Federal Criminal Practice Blog

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The NYSACDL has published its latest edition of Atticus, focusing on the organization’s often unsung and unknown efforts to influence the legislative process.  It includes my article addressing three recent Second Circuit decisions, including Capers (setting up some serious hurdles to the admission of statements obtained through a “two-step”– question first, Mirandize later – interrogation procedure), Cossey (“a sentencing decision that relies on factual findings that were unsupported in the record . . . seriously affects the fairness, integrity, and public reputation of judicial proceedings”), and Brown (“when a claim of ineffective assistance of counsel is first raised in the district court prior to the judgment of conviction, the district court may, and at times should, consider the claim at that point in the proceeding.”) 
As this blog has often pointed out (see here and here), the investigation and prosecution of lawyers for their lawyering is different.  Because these cases carry the potential to chill creative and zealous advocacy, they merit special precautions and scrutiny.  In fact, the ABA includes several recommendations in its "Standards on Prosecutorial Investigations" on how defense counsel should be prosecuted, including noting that "the prosecutor’s office should protect against the use of false allegations as a means of harassment or abuse that may impact the independence of the defense counsel or the Constitutionally protected right to counsel."  (Click here for the complete set of standards.).  That's not to say that lawyers should get a free pass with the claim that their conduct was mere advocacy (see here for Professor Gillers' tough comments on lawyers who hide behind their advocate status), but the line between ethical advocacy and criminal conduct can be a fine one and in the eye of the beholder.    

This fascinating issue will be the subject of a roundtable discussion at the Association of the Bar of the City of New York tomorrow evening from 6:30 to 8:30 p.m.  Conceived and organized by this blog author, on behalf of the Criminal Law and Professional Responsibility Committees, it features Gerald Shargel, Daniel Alonso, Barry Bohrer, AUSA Jon Kolodner and Professor Ellen Yaroshefsky.  It will be moderated by the Hon. Carol Bagley Amon of the Eastern District of New York.  For good measure, the program is free and offers two CLE credits in ethics.  There is still time to register (see here), but space is filling up fast!

Update [May 12, 2010]: The New York Law Journal has this report on the debate.

Throwing out the convictions of Robert Simels’ associate for witness tampering among other charges, EDNY Judge Gleeson found in United States v. Irving, 2010 WL 430952 (E.D.N.Y. February 8, 2010), that there was insufficient evidence to support the “sizable inferential leap[s]” necessary to find the associate knew of Simels’ “hair-raisingly criminal” plans.  The case, previously discussed here and here, is notable because of what it says (and doesn’t say) about “mere association” in a criminal case, and for its discussion of the standards applicable to sufficiency challenges.  

Mere Association Not Enough

Irving may have been Simels’ law associate, but that fact does not dilute or alter the well-established principle that “mere association with those implicated in an unlawful undertaking is not enough to prove knowing involvement.”  Notably (and rightly) absent from the decision is any suggestion that Irving, by virtue of her training, status and professional responsibilities as a lawyer, should be held to a different standard of criminal liability:

Specifically, Irving’s association with Simels and her presence in his law offices were insufficient to establish that she aided and abetted his crimes, even if her actions assisted him and indeed even if she were aware that he was committing a crime. As I instructed the jury at trial, the government was required to prove beyond a reasonable doubt that Irving herself acted with the specific intent to influence or prevent the testimony of the witnesses through intimidation, threats or corrupt persuasion.

Government’s Case Less than the Sum of its Parts

In a lesson on effective summation, the decision deconstructs the government’s case against Irving in painstaking detail, showing how she was simply not present for any of the crucial meetings in which Simels was charged with plotting to intimidate witnesses, and how her various emails and memoranda did not establish, as the government claimed, that she knew of any plan to “neutralize” witnesses by illegal means.  The court goes on:

It often happens that the whole of the government’s case is greater than the sum of its parts . . . However, that is not the case here.  Indeed, when the evidence against Irving is viewed from a broader perspective, it is arguably less than the sum of its parts, for the theory that Simels implicated Irving in his crimes made no sense. Simels had been a criminal defense attorney for more than 30 years.  Irving was a young, inexperienced attorney. When she began working for him in December 2006, Simels had already begun defending Khan.  Simels had numerous reasons to involve Irving in his many legitimate lawyering functions but none to involve her in his illegal activity.  

Competing Inferences of Guilt and Innocence

How should a court assess a sufficiency challenge where the evidence gives equal circumstantial support to a theory of guilt and a theory of innocence?  Not clear under Second Circuit law, Judge Gleeson points out, noting decisions that give opposing answers.  So he applies the more stringent formulation, “which requires deference to the jury’s verdict even where a verdict of not guilty would have been equally supported by the evidence at trial.”  But even under this standard, he notes that

[T]he Second Circuit has emphasized that where a fact to be proved is also an element of the offense, “it is not enough that the inferences in the government’s favor are permissible.”  The court “must also be satisfied that the inferences are sufficiently supported to permit a rational juror to find that the element, like all elements, is established beyond a reasonable doubt.”


This was a case where Judge Gleeson had a “very real concern that an innocent person may have been convicted’ – a concern, I would argue, that is heightened in cases involving prosecutions of lawyers for acts of advocacy, because jurors may not fully appreciate the dictates and ethics of zealous advocacy.  Processes at the core of advocacy – withholding judgment, demanding the development of additional facts, and embracing the concept that memory and personal narratives can be fluid – are often viewed by non-lawyers as manipulative and relativistic.  For example, as Judge Gleeson points out (but a non-lawyer may not immediately grasp): “There is nothing remotely criminal about a defense attorney telling a defense investigator that a particular witness could offer damaging testimony against the defendant at trial.  And Irving’s act of giving [a witness’s] address to a person acting as an investigator for the defense is innocuous.”  Luckily for Irving, her trial judge knows the difference between lawyering on the edge of ethics and lawyering that spills over into criminal conduct.

Lawyers: Javier Solano, Lawrence Berg, Law Offices of Javier A. Solano, PLLC (Defendant); AUSAs Daniel Brownell, Steven D'Alessandro, Morris Fodeman.

Behind the convictions of criminal defense lawyers Robert Simels and Arienne Irving yesterday on charges of witness tampering and obstruction of justice is a profound question: should there be different rules for the prosecution of lawyers?  The Simels prosecutors thought yes, and drafted a unique protocol for the minimization of communications intercepted under a Title III warrant.  EDNY Judge Gleeson disagreed.  In United States v. Simels, 2009 WL 1924746 (E.D.N.Y. July 2, 2009), he suppressed the fruits of the Title III surveillance because the protocol was internally inconsistent and improperly minimized dissemination rather than the initial interception.  In addition to being a detailed primer on Title III minimization issues, especially in the context of privileged communications, the decision joins its companion, discussed here, as another important landmark in the small body of jurisprudence on how (and how not) to prosecute a lawyer for an act of lawyering. 


As part of an investigation into allegations that defense attorneys Robert Simels and Arienne Irving were seeking to influence witnesses in the upcoming trial of their client Shaheed Kahn, the government obtained an order under Title III permitting it to intercept communications between Simels, Irving and Kahn, in the attorneys’ visiting rooms at MCC. 

Because the targets included two lawyers, the order contained two minimization provisions, both proposed by the government.  The first was a standard provision, requiring the monitoring agents “to minimize the interception of communications not otherwise subject to interception under [Title III], including . . . privileged communications.”  The second directed the agents to record (without listening to) all communications between Simels or Irving and their client, and provided for after-the-fact minimization by “Wall Agents” and a “Wall AUSA.”

Two meetings were recorded under the order, and only the second minimization directive was followed (in other words, the meetings were recorded in their entirety and not contemporaneously monitored).  Simels and Irving were later indicted on obstruction of justice and witness tampering charges, among others.  They moved to suppress the fruits of the wiretap surveillance because of a failure to minimize. 

Minimization Cannot Occur After the Horse Has Bolted

Granting the motion and suppressing the communications, Judge Gleeson found that the government’s minimization efforts here were unreasonable, and the post-interception minimization procedure violated Title III.  For one thing, the two minimization provisions in the order were internally inconsistent.  “By definition, an agent cannot minimize the interception of communications that should not be intercepted by intercepting all communications and sorting them out later.”  Moreover, while Title III permits post-interception minimization in two circumstances (where the communications are in code or in a foreign language), neither applied here.

[T]he way to avoid intercepting privileged or nonpertinent communications (as opposed to merely avoiding the unlawful dissemination of communications that should never have been intercepted in the first place) is take reasonable steps not to intercept them. Automatically recording everything, even where that is followed by a post-interception minimization protocol, virtually guaranteed the interception of communications the government should not have seized. The post-interception minimization may have closed the barn door, but the horse was already gone . . . When the government deliberately intercepts nonpertinent communications, it is no comfort to those whose privacy has been invaded that only government actors not involved in a particular criminal investigation will be listening to them.

Privileged Communications Are Not Special

The prosecutors had taken pains to avoid disseminating privileged communications, but Judge Gleeson debunked the idea that privileged communications should not be intercepted in wiretaps.  “Communications undoubtedly occur that are both pertinent to the crimes enumerated in an order issued pursuant to 18 U.S.C. § 2518 and privileged under some other body of law, and nothing in Title III prohibits the interception of such communications based on their privileged status.” 

Good Faith Not a Defense

Although the court found that the prosecutors’ good faith was “indisputable,” that was not relevant to the outcome.  Title III has its own statutory exclusionary rule, and Judge Gleeson found “no indication in the statute that good faith is relevant to the operation of this exclusionary rule.”


In developing their ill-fated protocol, the Simels prosecutors, to their credit, recognized the serious ramifications of bugging MCC’s attorney interview rooms.  But from a defense perspective, if you’re challenging the fruits of such interceptions on minimization grounds, the horse has already bolted.  What is far more interesting here is what led to the wiretap authorizations in the first place: several visits to Simels’ law office by a cooperating witness wearing a wire, who proceeded to discuss defense strategy in Khan’s case with Simels and Irving.  Judge Gleeson had denied Simels’ concededly “novel” motion to suppress these consensual recordings and their fruits on the grounds that the government’s use of a wired cooperator in these circumstances was unconstitutional.  But the motion begs the important question of whether there should be some formal rules requiring judicial supervision before wired cooperators are deployed into a law office.  Bad lawyers do not deserve special treatment, but aggressive advocacy does, and that kind of advocacy may be chilled by the kinds of highly intrusive surveillance and investigative techniques employed in this case.

The conviction last Friday of handbag magnate Frederic Bourke for bribing the government of Azerbaijan is probably enough on its own to strike fear into those doing business in the developing world – especially in countries with a high score on the Corruption Perceptions Index.  But an evidentiary ruling in this high profile FCPA case may generate some serious cost-benefit analysis in boardrooms.  In United States v. Kozeny, 2009 WL 1514369 (S.D.N.Y. May 29, 2009), SDNY Judge Scheindlin ruled that the government may introduce background evidence of corruption as part of its proof that the defendant consciously avoided knowing about the bribes at issue.  (Another interesting decision in the case is discussed here.)  The May 29 decision includes a detailed primer on the conscious avoidance doctrine, and is notable as the first reported application of the doctrine in an FCPA prosecution.  It is also notable as an illustration of how a defendant can score an “own goal” by doing innocence or cooperation proffers in a triable case.  


The defendant, Frederic Bourke, was charged with violations of the FCPA for allegedly making payments to Azeri officials to encourage the privatization of the State Oil Company of the Azerbaijan Republic and to permit him and others to participate in that privatization.  He moved in limine to preclude the government from introducing at trial evidence of corruption in Azerbaijan to prove his knowledge of the bribes at issue.  Under the FCPA, knowledge of a circumstance may be established by evidence that “a person is aware of a high probability of the existence of such circumstance, unless the person actually believes that such circumstance does not exist.”  The evidence the government sought to introduce included “that Azerbaijan was known to be a corrupt nation, that the post-Communist privatization processes in other countries have been tainted by corrupt practices, that SOCAR was a strategic asset of Azerbaijan, and that Kozeny [Bourke’s co-defendant] was notorious as the ‘Pirate of Prague.’”  

Conscious Avoidance and the FCPA

Agreeing with the defendant that the government may not introduce background evidence of corruption to show that he “should have known” that Azeri officials were being bribed, Judge Scheindlin held that here, however, the purpose of the evidence was to show that “a person of Bourke’s means, who was considering making a large investment in a venture in Azerbaijan, would have at least been aware of the high probability that bribes were being paid.”  As such, it was relevant and admissible.  

Defendant and Attorney Proffers

Critically, the court found no prejudice because the government would be able to establish the necessary factual basis for a conscious avoidance instruction.  In fact, the government’s factual basis rested on the defendant’s own admissions in proffers to the government.  Upon learning that he was the subject of a government investigation, Mr. Bourke appeared for a proffer session with the prosecutor, and admitted that he had been “warned by his counsel that Azerbaijan was the ‘Wild West’ and that doing business in Azerbaijan was like the movie ‘Chinatown,’ where there are ‘no rules.’”  For good measure, one of his lawyers had turned over a recording of a conversation between Bourke, another investor and their attorneys in which Bourke revealed his knowledge of the dark side of business in Central Asia, e.g. “Do you think business is done at arm’s length in this part of the world?” (There are some intriguing waiver issues here, but the decision doesn’t explore them, only to note that everyone appeared to agree that the defendant had waiver his attorney-client privilege in his proffer.)

Imputing Others’ Knowledge to Defendant

Finally, the decision addresses another unusual and important issue: the circumstances under which the government may introduce and impute to the defendant evidence of a third party’s knowledge.  Here, this knowledge could be imputed to Bourke based on his travels in a private jet with Viktor Kozeny (the alleged mastermind behind the SOCAR investment)and Bourke’s friendliness with Kozeny's “inner circle.”  “Based on these [close business] relationships the jury has a fair basis to infer that the knowledge of these individuals can be imputed to Bourke.”


Much ink will be spilled on the conscious avoidance doctrine in an FCPA prosecution.  But a lesson we can all (re)learn from this case is that proffers to the government in criminal cases can have a huge downside and should not be entered into lightly.  There may have been compelling strategic reasons for Bourke's proffer in this case, but it always astonishes me how often and easily lawyers will escort the clients in for meetings with the prosecutors, instead of proceeding by attorney proffer or asserting the right to remain silent.  As a wily criminal defense lawyer once said to me, “nothing is often the perfect thing to say and an excellent thing to do.”  

Lawyers: Harold Haddon and  Saskia  Jordan, Haddon Morgan Mueller Jordan Mackey & Foreman P.C., John Cline and K.C. Maxwell, Jones Day LLP, Dan Webb, James Reich, Jr. and Christopher Paolella, Winston & Strawn LLP (defendant); AUSA Harry Chernoff


Guest Contributor Justin M. Sher, Esq., writes:

In United States v. Rivera, 2009 WL 1059641 (S.D.N.Y. Apr. 13, 2009), SDNY Judge Baer held that a defendant could not waive his lawyer’s potential conflicts of interest where the lawyer had previously represented two co-defendants and shared an office suite with her father, who represented a third co-defendant.  The case is significant because the court concluded that it was obliged to disqualify the lawyer, notwithstanding her client’s waiver, because of multiple potential conflicts.


The defendant, Hector Rivera, was charged along with 13 other defendants with violating the Hobbs Act by conspiring to hijack Federal Express tractor-trailers.  Mr. Rivera’s lawyer, Stacey Richman, Esq., had previously represented two of Mr. Rivera’s co-defendants and continued to share an office with her father, Murray Richman, Esq., who represented a third co-defendant.  At the government’s request, the court held a hearing pursuant to United States v. Curcio, 25 F.3d 146 (2d Cir. 1994), to determine whether Ms. Richman’s conflicts of interest were “actual, potential or nonexistent.”  Before accepting a waiver of such conflicts, Curcio further obligated the court to (i) advise Mr. Rivera of the dangers that arise from Ms. Richman’s conflicts of interest; (ii) determine whether Mr. Rivera understood those risks and freely chose to take them; and (iii) give Mr. Rivera time to digest and contemplate the risks. 

During the hearing, Mr. Rivera received independent legal advice from another lawyer.  At the conclusion of the hearing, Mr. Rivera offered to waive Ms. Richman’s potential conflicts of interest.

Considering the “multiple conflicts of interest together, rather than in isolation,” the court held that the potential conflicts posed by Ms. Richman’s representation could evolve into actual conflicts that were among the “narrow category of conflicts that cannot be waived.” Rivera, 2009 WL 105964, *2 (emphasis added).  The court explained that it had no reason to doubt the professionalism of Ms. Richman or her father but that it was precisely because the court expected Ms. Richman to abide by her ethical duties that the court was concerned about her potential conflicts of interest. 

First, the court found that Ms. Richman owed continuing duties of loyalty and confidentiality to the two co-defendants who were her former clients.  If either co-defendant testified in a way that was adverse to Mr. Rivera’s interests, the court determined that there was a substantial likelihood that Ms. Richman’s ethical obligations would impair her ability to zealously advocate for Mr. Rivera by, for example, limiting her ability to attack her former client’s credibility on cross-examination.

Second, because she practiced law in the same office and shared a staff and fax machine with her father, the court found that Ms. Richman might owe ethical duties to her father and his clients, one of whom was also a co-defendant.  The court recognized the possibility that Ms. Richman might overhear or come across information that would be helpful to her client but also would be “ethically off limits.”  The court concluded that this too could impair her ability to effectively represent Mr. Rivera.

The court held that the likelihood that one or more of Ms. Richman’s potential conflicts could burgeon into a “severe and actual conflict” created an intolerable risk and “obliged” the court to disqualify Ms. Richman.


United States v. Rivera is noteworthy for the court’s holding that several potential conflicts of interest were, in aggregate, sufficiently severe that they obliged the court to disqualify a lawyer notwithstanding her client’s offer to waive the conflicts.  By finding that it was “obliged” to disqualify Ms. Richman, the court implicitly determined that Ms. Richman’s potential conflicts were analogous to “an actual conflict that is so severe as to indicate per se that the rendering of effective assistance will be impeded . . . .”  See United States v. Perez, 325 F.3d 115, 126 (2d Cir. 2003) (emphasis added).

The case is also noteworthy for the court’s suggestion that lawyers who share an office and other resources may owe ethical duties to each other and each other’s clients.  The court did not find that Ms. Richman worked for or was otherwise affiliated with her father’s law firm or that she and her father presented themselves to clients as a single firm.  Nor did the court explicitly assign significance to the lawyers’ relationship as father and daughter, although this fact certainly makes the case unusual and distinguishable from most other scenarios.  The court noted only that Ms. Richman and her father shared an office, staff and fax machine and observed that, as a result, they could come across confidential information concerning each other’s clients.  The case thus suggests that lawyers who merely share an office and certain other resources face a greater risk of being disqualified if they represent clients with potentially divergent interests.

In a recent speech, NYU Professor Stephen Gillers makes the point that in our highly regulated society it would be impossible to operate Bernie Madoff’s business without the help of lawyers and accountants.  “Did none of them know?” he asks.  “Did none have suspicions?  Did they look the other way?”  The questions could be asked not just of Madoff’s Ponzi scheme, but any number of other recent corporate scandals that have roiled the financial markets.  Of course, it’s one thing to question the ethics of the professionals who have facilitated schemes that have led to catastrophic losses.  It’s another to prosecute them.  The cautionary tale of United States v. Ruble, 2009 WL 911035, (S.D.N.Y. April 2, 2009), is a notable landmark in the jurisprudence relating to the prosecution of lawyers for acts of advocacy.  It illustrates the fine line between creative advocacy and criminal conduct, and is likely to lead to a significant appellate decision on the quantum of proof necessary to convict a lawyer for participation in his clients’ fraud.   


Ruble, a former partner at two major New York law firms, was convicted of tax fraud arising out of his issuance of “opinion letters” validating the legality of purported investment schemes that permitted the investors to report large tax losses.  Prosecutors described it as the largest tax fraud prosecution in U.S. history, generating hundreds of millions of dollars in phony tax losses and costing the U.S. treasury more than $1 billion in lost tax revenue.  Ruble moved for a judgment of acquittal, arguing that the evidence was insufficient to permit the jury to find, beyond a reasonable doubt, that he acted willfully.  The motion was denied from the bench.  In this decision, SDNY Judge Kaplan explains his reasoning. 


In order to establish that the tax shelters at issue lacked economic substance for criminal tax purposes, the court held, the government had to prove, among other things, that “the relevant taxpayer had no business purpose for engaging in the transaction apart from creating the tax deduction” and “there was no reasonable possibility that the transaction would result in a profit.”  Here, the jury was entitled to conclude that “Ruble knew or consciously disregarded the fact that the investors had no non-tax reason for doing the deals and that the deals, as designed and implemented, offered no reasonable possibility of any profit apart from their tax benefits” (my emphasis).  In fact, when he later sentenced Ruble to 6 ½ years in prison, Judge Kaplan noted that the scheme “didn’t pass the smell test from Day 1.”

The court also noted that “the intimacy of the relationship” among Ruble and participants in the scheme supported the finding.  There was “abundant evidence” that these other participants “were well aware that the taxpayers had no business purpose and that there was no reasonable opportunity for profit” and “the jury was entitled to find that [they]  imparted this information to Ruble.”


It would be ironic if Ruble had been convicted on a conscious avoidance theory.  After all, in an adversarial system, conscious avoidance is what advocates practice.  We argue the good facts; our adversary the bad.  In Ruble’s case, however (like the situation of the authors of the Bush administration’s torture memos), his advocacy would not be probed and challenged by others.  Rather, it would be filed away by the client, to be dusted off in the event the conduct was ever challenged.  Should your advocacy be subjected to higher scrutiny because you’re preaching, unopposed, to the choir?  When must a lawyer stop advocating his/her client’s case and instead police it? 

Under the rules of ethics, a lawyer may not disclose a client’s fraud without actual knowledge of it.  Under Second Circuit precedent, however, a lawyer may be prosecuted for participation in a client’s fraud, where the lawyer deliberately turned a blind eye to the client’s wrongdoing.  In other words, what may pass muster ethically may nonetheless expose the lawyer to criminal liability.  The line between zealous advocacy and criminal conduct may be easy to discern in a fraud that doesn’t pass the smell test, but other frauds may not be so obvious.  And clients aren’t always forthcoming with all the critical facts, especially if they have only retained the lawyer to give them cover.

See Archives for all posts since September 2007.