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You've pleaded guilty to a federal crime and face imprisonment—maybe even 10 years—and have basically thrown yourself on the mercy of the court. Frankly, some judges aren't so merciful at all. Now, typically defendants aren't sentenced to the “maximum”; but still, if the prosecutor is asking for stiff time, the judge will pay great attention to that recommendation. Even more so if the probation department's report agrees. Your attorney makes all the legal arguments for why leniency is appropriate. And he and your supporters write the judge expressing your considerable remorse and good works.

The judge, though, has heard it all a thousand times before—maybe more. You might even break down and cry in the courtroom on that day of judgment—believe me, the judge has seen that many times too! Actually, there are some defendants, actually most, who aren't remorseful about their crime; rather, they simply regret that they got caught and that their families have to suffer. Many defendants may talk the talk, but without sincerity. Yes, some pull it off better than others and, depending on the judge, their display may be believed. Or not.

I recognize how this sounds, but think about how often you have discredited the “remorse” of others, including (maybe especially) your children. You may want to believe them because they're family, but deep down often you simply can't!

So the question may come down to this: How can a judge confidently credit the bona fides of a defendant's stated remorse in order to accord him leniency? And even if the defendant's remorse is not overly sincere, can a judge somehow convert the defendant's stated sentiments into something that actually benefits society? For, indeed, “general deterrence”—the goal of deterring the criminal conduct of others—is a key component of sentencing. That is, a sentence not necessarily (or at least only) designed to deter you, but to deter the community at large.

Judge Valerie E. Caproni of the Southern District of New York, not at all shy when sentencing criminal defendants, particularly white-collar ones, may have hit on just the right answer. That is, to transform ostensible (or even real) remorse into meaningful and bold action. It was particularly the case here where Kevin Shuler not only cooperated after being charged, but gave critical testimony in the Buffalo Billions investigation which led to the convictions of four others—a serious New York corruption scandal. Judge Caproni, although these weren't her words, basically told Shuler: You want me to sentence you to probation (or, “supervised release” as they call it in the federal system) even though you admit that your crime was serious? Okay, but, sentencing you to a term of probation with periodic visits to your officer (perhaps with a urine test as part of the bargain), even combined with some undirected community service of 400 hours, isn't nearly enough.

Shuler's attorney, Terrence Connors, asked for a probation sentence requiring Shuler to appear before students and tell them what he did: “He just may be the person who stops some business student or one law student from taking a path that should not be travelled,” counsel told the court. And Judge Caproni not only agreed, it had been precisely what she planned to do (complimenting Connors for having done his homework by looking at other sentences Judge Caproni had meted out: “Mr. Connors obviously had a gremlin in my computer.”). So, at least one-third of Shuler's community service “should be spent talking to college students, or business groups, or law students about business ethics and the risks of failing to adhere to principles of integrity and honesty when dealing with the government.” Judge Caproni told Shuler to seek out classes and clubs to talk to, which is a better way to use his time than working in a soup kitchen: “I want you to be the guy out there who is talking about the importance of business integrity.”

And so Shuler will presumably tell students exactly what he did, exactly what the potential consequences for doing it were, and exactly why he became a sacrificial lamb, now exposed to public obloquy, so that still-impressionable students don't do the same stupid, jail-worthy things. Just imagine, students getting a dose of what could possibly happen to them, from someone who it has already happened to and only “escaped” (after indictment, cooperation, shaming publicity and trial) by the skin of his teeth.

This type of sentence is actually music to my ears. I actually had recommended that such a regimen be proposed to his sentencing judge by a defendant I know, before sentence was actually imposed. The problem, his able lawyers told me, was that the defendant wouldn't introspectively have been able to pull it off. Perhaps, in his case, he wasn't truly remorseful or couldn't candidly articulate the type of remorse that would impress that judge (they may well be different). Or, the defendant wouldn't have gotten a big enough bang for his buck from the judge, particularly given the likely stiff sentence he would receive under any circumstances—he wasn't a cooperator. Meaning, the judge might make the “remorse lecture circuit” only a small part of his sentence—at the tail end after a lengthy prison term. Moreover, that defendant had been convicted after trial and intended to appeal the conviction. A post-conviction admission of guilt (a predicate for exhibiting remorse), might have compromised his appeal. Maybe, all true.

Still, as in the case of Kevin Shuler, who had actually shown remorse by cooperating with the government, most defendants who are prosecuted, at least in the federal system, plead guilty. Counsel for every such defendant facing potential imprisonment needs to urge the sentencing judges to be creative and think outside the box. And they need to come to the judge with their creativity, particularly after studying the judge's track record. Shuler's capable attorney, Terry Connors of Buffalo, did just that by asking a typically “tough” sentencing judge to help enhance general deterrence in sentencing a defendant perhaps already on his way to demonstrating true regret for what he had done.

Kudos to Connors. And kudos to Judge Caproni.

Joel Cohen, a former prosecutor, is a senior counsel at Stroock & Stroock & Lavan. He is an adjunct professor at Fordham Law School.