Interview with Alexandra Shapiro

I had the privilege of talking to Alexandra Shapiro, a highly respected criminal defense and appellate attorney about her career, her thoughts on important developments in the law, and her new book. Alexandra was a law clerk for Justice Ginsburg and recently wrote a tribute to her in the Columbia Law Review titled Reflections on Justice Ruth Bader Ginsburg and her Approach to Criminal Law and Procedure. In this interview, there is much to learn from one of our country’s great legal minds. I am honored she is willing to share her knowledge and love of the law with us. 

Can you share with us your path to becoming a criminal defense attorney? Are there any particular areas of the law that you are more focused in your practice?

I’ve always been interested in criminal law. And as a young lawyer, I was eager to try cases, so after clerking for Justice Ginsburg, I became an AUSA in the Southern District of New York. I served in that Office’s criminal division for five years and then did white collar work at a big international law firm. Most of the work involved internal investigations and company representations, but I also represented some individuals. One of the most interesting (and most rewarding) cases I handled early in my career in private practice was an insider trading case that went to trial twice—first, we got a hung jury, and then after the second trial the judge granted a post-conviction acquittal. Starting a small firm gave me the opportunity to do more criminal defense work of that type, representing individuals in litigated cases.

Shapiro (right) with Justice Ruth Bader Ginsburg

These days I mostly handle white collar criminal defense, regulatory defense, and appeals. I also do complex civil litigation, but the primary focus of my practice in the last five years has been appeals and criminal work. The appeals are both criminal and civil. In the criminal area, the majority of my appeals are in white collar cases—prosecutions for insider trading, securities fraud, wire and mail fraud, public corruption, tax fraud, and the like. I have also done pro bono appellate work on criminal law and procedure issues, including amicus briefs (a couple of which have been cited by the Supreme Court). On the civil side, some of it is commercial, but in recent years most of the civil work has been constitutional law, election law, or administrative law matters. So, the civil practice is a little more varied, but the majority of my practice is focused on white collar criminal defense. 

As a trial lawyer I am always mindful of needing to properly preserve an issue, which is sometimes hard to do when you are wearing multiple hats. Do you work with trial counsel during the pretrial and/or trial phase to help develop issues that could eventually form the basis of an appeal? 

Absolutely. I usually get retained after somebody else lost the trial, but I do get involved at the trial level too. In fact, in recent years, I've had two significant cases where I've been involved in the trial. In one of those cases, I was cross-examining witnesses in addition to handling motion practice, requests to charge, the charge conference, arguing various evidentiary issues and making sure we were preserving all our issues for appeal. That was the second trial for Dean Skelos, whom I had represented in his first appeal (we won, which led to the second trial). And then there was also a case I did a few years back where my client, a Chinese businessman, was accused of bribing two UN officials. Tai Park was the lead trial lawyer, and early in the case, he brought me in to handle various complex legal issues. 

I think that it's critical, if a client has the resources, to have someone with appellate experience focused on the legal aspects of the trial—someone who has an appellate perspective and a deep understanding of criminal law who can help spot and preserve potential appellate issues. One of the most frustrating things for me as an appellate lawyer is to find that something important wasn't preserved, or that I have to argue an issue in a different way to the appellate court. It’s totally understandable, because trial lawyers are in the heat of the battle and focused on contesting the government's account of the facts. But it is easy to fail to preserve issues inadvertently, especially if you haven’t done many appeals. So, yes, that's definitely part of the work that I do, and I enjoy doing it. 

I think it is important for trial lawyers to stay current with developments and trends in the law. A recent important case in the white collar space is Kelly v. United States. Can you share your thoughts on the importance and impact of this case and its possible application on future white collar prosecutions?

Kelly is a really important case, both in terms of its reasoning and holding, which I'll discuss, but also because it represents a trend in which the Supreme Court has been narrowing federal criminal statutes in the last couple of decades. Lower courts tend to interpret some of these very broadly written or amorphous federal statutes, like the honest services statute and the wire fraud statute, in a very expansive way. So, when creative prosecutors come along with a new theory and use it to obtain a conviction, the lower courts tend to want to uphold it. On the other hand, in a number of cases dating back all the way to McNally v. United States in 1987, the Supreme Court has been very careful to interpret these statutes more narrowly. I think Kelly is emblematic of that. Kelly involves the wire fraud statute (and another property-fraud statute), and its holding applies equally to mail fraud. These statutes are often used in garden-variety fraud prosecutions, but there are also instances in which prosecutors use them to pursue more creative theories when they believe a business practice is distasteful or unethical—even if it is not illegal. 

The Kelly case involves the Bridgegate scandal, where New Jersey officials working under Governor Christie commandeered three lanes of the George Washington Bridge to divert Fort Lee traffic to punish the mayor of Fort Lee for refusing to endorse Governor Christie's reelection campaign. They invented this cover story about a traffic study to carry out their plan. There was no question they lied, but the question was whether the object of their deceit was to obtain the “property” of the Port Authority of New York and New Jersey. The Supreme Court said no.

There were two important factors in the Court's decision reversing the conviction. One aspect relates to whether the defendants’ object was to obtain property of the transit authority. The Court said this isn't property, because it’s not property in the government's hands in the traditional sense. It's not something the government can sell—the government is just exercising its regulatory authority over how these traffic lanes are going be used. In that regard, the Court reinforced a principle that it had already unanimously announced in 2000 in a case called Cleveland v. United States, which involved a fellow who made false statements to get a poker license from the State of Louisiana. The Court held that the license isn't property in the hands of the State, because the State is not in the video poker business. This may violate some other law, but it’s not mail fraud or wire fraud because the defendant is not trying to get the State's property. In Kelly, the Court expanded on that principle and made clear that when you're talking about alleged frauds against the government, the object of the fraud must be to take something from the government that has the characteristics of traditional property in the hands of the government—in other words, something that has financial value to the government. This is the part of the holding that really reinforces and expands on Cleveland. 

The other aspect of the Kelly holding relates to the government’s argument that the use of the time and resources of the government-paid employees at the Port Authority was enough to establish the property element of the crime. The Supreme Court held that if there was any loss (because the employees were diverted to the traffic study), it was incidental to the fraud, and not the object of the fraud. This is important because it raises questions about some far-reaching property prosecutions that have been upheld in the past under something called the “right to control” doctrine. Some of these cases involve situations where the government alleges that the object of the property is to deprive the victim of its right to control its assets—a pretty nebulous concept. For instance, there's a Sixth Circuit case where the court rejected the prosecution of a defendant alleged to have illegally distributed controlled pharmaceutical products. This defendant had lied to the pharmaceutical companies that she was buying the drugs from about what she was going to do with the drugs after she purchased them. She was charged with wire or mail fraud, and the Sixth Circuit reversed her conviction. The court held that she didn't deprive the companies of any property because she paid their asking price. Essentially, it held that the supposed victims got the benefit of the bargain; the fact that the woman lied about this other issue (her resale plans) doesn't make it a property fraud. In that case, the court rejected the prosecution’s theory, but there are lots of similar cases in which other circuits have upheld wire or mail fraud convictions. In general, these cases involve a claim that there is some sort of lie, but the victim wasn't ripped off in any way because of the lie. It's just something ancillary and not really at the heart of the bargain. 

There's language in Kelly that shows why this type of “right to control” argument shouldn’t work, because the object of the fraud is not really to inflict economic harm by taking the victim’s property. Lawyers handling these types of investigations or prosecutions should think hard about whether the charged conduct, even if proven, really would be a property fraud. It is true that the Supreme Court—before and indeed after Kelly—has denied certiorari on a number of petitions raising challenges to this “right to control” doctrine. But I believe that at some point when the right case comes along, the Court will take this up, and it could well rule that the doctrine is invalid. So it’s important for defense lawyers handling fraud cases to bear these issues in mind.

Should these challenges be made pretrial or during trial? 

I think this is a strategic question that counsel needs to think about. In some cases, you may want to file a pretrial motion to try to get the indictment dismissed. Of course, you know, not very many get granted. It can be helpful to preserve the argument; on the other hand, the government may just supersede and try to fix the problem, depending on the facts and the nature of the charges. You would have to make a tactical judgment about raising these issues pretrial or at a Rule 29. You need to make sure you submit jury instructions that support the argument you are going to make and consistent with what you think the law should be, and then preserve your objection at the charge conference. But I think this question about the pretrial motion is always a difficult question in many contexts, and it may depend on your assessment of whether this might be the rare case in which the judge would seriously consider granting the motion. I’ve handled it both ways, and it’s a very case specific decision.

Are there other examples where you think the courts are focused on narrowing the application of certain statutes?

Another area that comes to mind involves the financial penalty statutes. One prominent example is forfeiture and the Supreme Court’s Honeycutt decision. Interestingly, the language in that statute is similar to the mail and wire fraud statutes, in that the word “obtain” features significantly in the analysis in Kelly and in Honeycutt, which says that the government can only forfeit property that the defendant has obtained. In Honeycutt, the Court held that forfeiture is not subject to joint and several liability; the government can only forfeit property from a defendant who has himself obtained or acquired the property in question. 

In the past, people didn't really think that much about financial penalty statutes. In fact, many years ago when I was an Assistant United States Attorney, it was an afterthought, and the government didn't always seek forfeiture. But a lot has changed since then, and the government has gotten very aggressive about trying to enforce these penalties, so the Honeycutt decision was important because it narrowed the application of the statute. 

Another related area involves restitution. There is a 2018 case called Lagos v. United States, which limited restitution relating to a victim’s attorney’s fees. In the white collar field, it is commonplace to see entities spend tons of money on legal fees. Whether a company’s lawyers are dealing with federal prosecutors in a criminal case, doing an internal investigation, or handing an SEC investigation, they can rack up enormous legal bills. There's this provision in the restitution statute that allows victims to get some compensation for certain expenses incurred in connection with “participation in the prosecution or investigation” of an offense. A lot of lower courts tend to defer to broad requests by company victims to recover their attorneys’ fees, even for things like sending associates to watch every day of a 2-month trial—which can add up to quite a bit in spite of the fact that the work the lawyers are doing is for the company but does not assist the prosecution in any way. In Lagos, the Court issued a decision requiring a showing that whatever attorney's fees are being sought as restitution must be fees incurred so that the company could assist the government in its criminal investigation or prosecution. An internal investigation conducted for the company’s own benefit, for instance, does not count. Both Honeycutt and Lagos are additional examples of Court narrowing the application of a federal criminal statute.

Considering that the Government has been more aggressively pursuing forfeiture and restitution, what should trial counsel be considering during plea negotiations or after trial? 

Some lower courts continue to try to limit the reach of Honeycutt, either factually or as applied to a different forfeiture statute that has the same language as the statute in Honeycutt. But Honeycutt is pretty clear, so it’s important to argue for strict enforcement of the decision. At a minimum, defense lawyers should definitely preserve these arguments, because eventually, if the lower courts deviate too much from Honeycutt, these issues will go back up, and I think the Supreme Court will enforce Honeycutt.

When it comes to plea negotiations you need to be up on the law so you can make these kinds of arguments to try to get the number down. Obviously, what's most important is keeping your client out of prison, but financial penalties can also bankrupt people. There are other good arguments to make beyond the ones we just discussed. For example, I’m handling a case now for an executive of a public company who is appealing his conviction for accounting fraud. At the eleventh hour, right before the sentencing, the government said that they would seek restitution, after having initially said they weren’t seeking restitution. The company asked for approximately $40 million in fees for various attorneys who had represented the company, the trial defendants, and several other executives during the SEC and criminal investigations. The district court denied the request, and we won on two different arguments. One of the arguments we made was that the company was not a victim of the offense, as the defendants were acting on behalf of the company when acting as the government charged. Judge Rakoff wrote a published opinion agreeing with our view of the law. It might be different in a different type of case, such as an insider trading case where the company is the victim, and the executives breached their duty to their employer. Nevertheless, I think this ruling may be helpful to defendants facing restitution applications in many securities fraud cases. It’s a good example of why you want to be on top of developments in this area of the law to help reduce the financial exposure your clients have, which can be extreme.

Later this year the Supreme Court will hear Hemphill v. New York and address the issue of whether a criminal defendant, based on an argument or introduction of evidence at trial, opens the door to the admission of evidence barred by the confrontation clause. Explain the importance of this case for the defense and its impact on Crawford?

The question in the case is whether a criminal defendant who "opens the door" to responsive evidence forfeits the right to exclude evidence that would otherwise be barred by the Confrontation Clause under Crawford and its progeny. The Hemphill case involves a shooting in which there was a dispute about who was the gunman. The defendant made an argument that the trial court said opened the door to the government introducing statements in another defendant’s plea allocution. It had to do with what type of gun was used. The New York State Court of Appeals said that was permissible and affirmed the conviction. There is a split among lower courts about whether the government can get around Crawford where the defense makes an argument that could be rebutted by evidence that would otherwise be inadmissible under Crawford. 

If the Supreme Court were to rule for the government, it would certainly blow a hole into Crawford. Particularly where the statement is something like a plea allocution or another defendant's post-arrest statement, this type of hearsay is unreliable but can be devastating to a defendant. I have no idea how the case is going to come out, but one troubling development since Crawford is that there have been some Supreme Court cases which have limited its scope. These are cases, for instance, exploring what type of evidence is “testimonial” and comes under the Crawford rule, versus what type of hearsay is not subject to Confrontation Clause scrutiny. The Court has become increasingly divided on these issues. There are a number of 5-4 decisions involving admissibility under Crawford, including a series relating to forensic tests. The earlier of these cases were decided in favor of the defendant, but in a more recent case in this line the Court ruled against the defendant, also 5-4. And that was before Justice Ginsburg passed away, so there is reason for concern about the future trend in this area. 

Until there is a ruling in this case, how would you recommend lawyers balance the need to advocate for their clients while not risking opening the door? 

This case is being argued in October and hopefully there will be a decision soon, but the outcome is impossible to predict. Until this case is decided, you don't want to risk forgoing an argument that gives you your best shot for an acquittal, but lawyers need to be mindful that the case is before the Supreme Court. I think how you handle these issues now has a lot to do with what jurisdiction you are in and how that jurisdiction has ruled on this issue of opening the door. If you aren’t in a jurisdiction like New York State, which allows the government to rebut with otherwise inadmissible hearsay, argue what you need to and take advantage of the good law in your jurisdiction. But in places like New York, you probably have to be a bit more careful because maybe the Supreme Court will uphold the Court of Appeals, and trial courts will have to follow the law that is on the books at the time of the trial. 

One thing counsel might consider is to raise this with the trial court prior to trial and inform the court that you want to argue X, but that this case is pending before the Supreme Court and try to get a pretrial ruling. At the very least, you preserve the issue if you decide you can't open the door under the current law. You need to make a proper record of what you would have done or argued so that if the Supreme Court reverses in Hemphill and you lose the trial you can take advantage of the good decision post-trial.

It’s clear you stay on top of developing issues in the law. That said, I heard that you recently finished a fictional novel, when did you find the time to do that? Can you tell us about it and what inspired you to want to write a book? 

I've always wanted to write a book. I had a secret desire to write fiction, but originally, I was thinking about writing a nonfiction book. Like many defense lawyers, I've occasionally had extremely frustrating experiences, not just in the usual heat of the battle, but situations where I believed a grave injustice was done in a particular case. Whether it's at trial or reading a trial record, defense lawyers see first-hand the effect of institutional unfairness that is built into the system. This makes it so difficult for defendants, even when they've got great arguments, to prevail. There was a particular case that I was thinking about writing a nonfiction work about. When it was over, I spoke to a published author about the idea of writing about the case. He said it's a very complicated case, so it is a going to be a little hard to make it accessible to lay people. He recommended that I write a novel instead, and I thought that was a great idea. I decided to invent a simple white collar case involving a questionable prosecution and tell a story that I hoped would engage not just lawyers, but also lay readers. My hope is to educate readers about the fact that unfairness exists in the criminal justice system, and can affect anyone, including defendants who have the resources to hire good lawyers. So that's how the novel came about. 

The title is Presumed Guilty. 

I’m not sure how I found the time. I started working on it during the pandemic and mostly worked on the book at nights and on the weekends. I took a book creator class that a business school professor at Georgetown runs, which anyone can join. It’s not expensive and it was a great class. They pair you up as you're writing with a development editor. I found that really helpful, because I'm a person who works best with deadlines and external pressures, and I felt like I had to answer to this developmental editor, whom I would meet with every week while I was working on the first draft. That helped give me the incentive to keep chugging along and churning out content. Also, having feedback along the way was invaluable.

When is the book coming out? How can someone find the book when it is released? 

It's going to be published in December of this year through New Degree Press, which is a hybrid publisher. There is a pre-sale campaign that launched Friday, July 23, 2021, for people who are interested in supporting the book. They can pre-order copies and get little perks such as a signed copy, ability to read the introduction early, give me feedback on the cover design and things like that. That campaign will go on for 30 days to raise money to pay the editors, the cover designers, and other marketing and publication costs. The book will launch in late December, and at that point it’s going to be available through Amazon and other major retailers. I'm also hoping to get the book into local bookstores because I'm a big supporter of indie bookstores. I expect it to be more widely available by January of next year.