Sentencing Law, White-Collar Crime

The Challenges Of White-Collar Sentencing

Balance is critical in making your case at sentencing.

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Man_in_jail-RFA recent New York Times article brought up something I think about a lot — the challenges of sentencing in white-collar cases.

The jumping-off point for the article was the recent sentencing of Wall Street scion Andrew Caspersen, who was sentenced to four years in prison earlier this month for a fraud that exceeded $38 million. The government wanted him to serve more than 15 years, but Judge Jed Rakoff — one of the most thoughtful judges in the country and a longtime critic of the federal Sentencing Guidelines — rejected that request. He accepted the defense’s argument that the crime was driven mainly by a gambling addiction, and not by an intent to hurt anyone.

The New York Times article squarely framed whether this is fair — whether an extraordinarily rich man with a fantastic lawyer should get a break that a poor defendant would almost certainly not get, due to the nature of the crime, the quality of his lawyer, or often, both:

Unlike those who commit street crimes, white-collar offenders are much more likely to be members of the middle class, and possibly even among the economic elite like Mr. Caspersen. They have the resources to present a sympathetic picture of their life while claiming that violations of the law were just aberrations from an otherwise exemplary life.

This is absolutely true. It’s hard to overstate the value of having a good lawyer at sentencing, no matter what the crime is.

A good lawyer can transform someone who might otherwise be seen as one-dimensional — a serial robber, or a fraudster — into an actual human being who, for various reasons, made a terrible mistake. Maybe he had a terrible childhood, or a substance-abuse problem, or a gambling addiction, or just got caught up in something that started small but then spiraled out of control. A good lawyer can also collect dozens of letters in support of his client, painting a much more nuanced picture of the person than the court would otherwise have.

And unfortunately, in the criminal justice system, you often get what you pay for. So the more money you have to spend on sentencing, the better the advocacy on your behalf is likely to be.

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But at the same time, there are challenges that arise more in white-collar cases than in traditional street-crime cases. Many white-collar defendants, for example, had pretty good childhoods and pretty good lives. Caspersen, for example, was born into enormous wealth and graduated from Groton, Princeton, and Harvard Law School — the Episcopalian hat trick.

So it can sometimes be hard to use a difficult personal history as mitigation evidence — although, to be fair, Caspersen did lose his longtime girlfriend on 9/11 and his father to suicide (while under government investigation, to boot). Not all street criminals had terrible lives, and not all white-collar criminals had perfect ones.

A privileged background can also lead judges to conclude that the defendant should have known better. If you grew up with a stable family and had a good education, it can be hard to argue that you had no choice but to do what you did. Jean Valjean, you are probably not.

Many white-collar defendants also have long track records of charitable giving and good-deed-doing. That’s certainly something a good lawyer will talk about, but it has its limits. Is it, for example, fair to give a break to a rich defendant who started a charitable foundation, when a poor defendant never would have had such an opportunity?

Even sentencing letters can be complicated. At a sentencing I handled recently, the judge — who had been on the bench for more than 25 years — said that we submitted more sentencing letters on behalf of our client than he’d ever seen in any previous case. But he also said that he didn’t think it would be fair to give the letters too much weight, because our client had the support and the resources to get letters that other, less fortunate defendants would not have. It’s hard to argue with that.

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In my experience, the best approach at sentencing is to be balanced, regardless of collar color. Talk about the client’s good deeds and the professional humiliation he’s suffered — but don’t overdo it. Talk about the effect that a long jail sentence will have on the client’s family — but don’t go so far that the judge will respond, as I have seen judges do, “He should have thought about his family when he decided to commit the crime.” Talk about his personal challenges, as Caspersen’s lawyer ably did with his gambling addiction — but don’t say that excuses everything.

Try to get the judge to see your client as a person, not as a defendant. Regardless of where we come from, most of us are greater than the sum of our parts. Most of us are better than the worst thing we’ve ever done.

Justin Dillon is a partner at KaiserDillon PLLC in Washington, DC, where he focuses on white-collar criminal defense and campus disciplinary matters. Before joining the firm, he worked as an Assistant United States Attorney in Washington, DC, and at the Civil Rights Division of the Justice Department. His email is jdillon@kaiserdillon.com.

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