A Second Chance, For the Judge

While it’s hardly new to have a federal judge spill his guts these days, it’s also not the norm for judges to put themselves on the line in full public view. To his credit, District of Connecticut Judge Stefan R. Underhill does so in a New York Times op-ed, in which he openly questions a sentence he imposed years ago.

In 2006, I sentenced a man to 18 years in prison. I have been wrestling with that decision ever since.

As a federal district judge, I’ve sentenced hundreds of people, but I’ve rarely agonized as much as I did over this man’s fate.

Before delving further, two things need to be understood. Judge Underhill’s reference to the hundreds of people he’s sentenced, and to the fact that he has wrestled with his 2006 sentencing decision, speaks well of him.  But then, he was charged with sentencing human beings, a judicial responsibility, for which he was poorly prepared.

Clearly very smart, he was certainly the sort of lawyer to end up on the federal bench.  But there is nothing in his background to suggest any competency, any understanding, that would enable him to sentence another human being to prison. And, while it’s clear that this wasn’t what he meant to say, the fact that he didn’t agonize over every sentence imposed is telling.

He was the enforcer for a brutal gang of drug dealers in Bridgeport, Conn., known as the Terminators, and had sold heroin, assaulted rival dealers and murdered a potential witness. But after a falling-out with the head of the gang, he turned over a stash house to the police and fled the state. When captured in 2001, he immediately confessed to the murder and later testified as a star witness for the prosecution.

So he was a bad dude who flipped as soon as it was his ass on the line.  To most people. being a rat, dropping a dime on your enemy (who use to be your bestest friends before he became the enemy), isn’t considered a positive character trait.  But this bad dude went into the government’s service. To Judge Underhill, that gave rise to his dilemma.

Thus arose my problem: He had committed horrible crimes, but he also seemed to be making an unusually sincere effort to atone for them. So which man was I sentencing? The murderer or the remorseful cooperator?

The prosecutor rewarded his cooperation by filing a so-called 5K motion, which allowed me to ignore the mandatory life sentence he otherwise would have faced. Still, after weighing the seriousness of his crimes, I sentenced him to 18 years, which was more time than even the prosecutor wanted.

What, in this mash of aggravating and mitigating factors, made Judge Underhill decide that 18 years, not 12, not 22, was the right length? He was freed from the Guidelines by the 5K1.1 letter, so it was left entirely to the court’s discretion. Why 18?

Long story short, Judge Underhill found himself near this fellow’s prison and paid him a visit. He pulled out all the usual certificates that nearly every prisoner collects. Lawyers see tons of them. Judges, apparently, not so much, so Judge Underhill found it special, that this guy over whom he antagonized now seemed to the judge not to need the next dozen years of imprisonment.

After I returned to my office, I contacted the prosecutor and his lawyer and encouraged them to find a way to get him released early. But they told me there was no straightforward way to shorten a federal inmate’s sentence, even if prison officials acknowledge that more jail time is a waste of time and money. So he had to stay in prison, at an annual cost of $30,000 to taxpayers.

Didn’t you know this? Had you ever practiced criminal defense before taking the bench to sentence human beings to prison, you would have known this. Yet, as a federal judge, you weren’t aware of the significance of the numbers that came out of your mouth, that there was no going back later if you blew it?

Congress should enact legislation that would allow every sentenced defendant one opportunity to petition his sentencing court for a reduction based on extraordinarily good conduct and rehabilitation in prison.

A second chance?  For whom, Judge? Whether this defendant’s good conduct and rehab were “extraordinary,” or utterly banal, isn’t nearly as clear from this op-ed as it seems to Judge Underhill.  What is clear is that a monstrously long sentence was imposed, seemingly without any appreciation of what it means, what it does, what purpose it serves.

A second chance to correct a mind-numbingly long sentence sounds like a great idea, and I applaud Judge Underhill’s willingness to come forward publicly in favor of it. But it’s impossible to ignore the length of the sentence imposed in the first place. It’s impossible to ignore the hundreds of other defendants sentence, who weren’t worthy of his agony.

There is one person, one function, left completely unmentioned in the discussion of the imposition of the original sentence. The defense lawyer. Did the defense lawyer not argue to the court that a far shorter sentence was more appropriate? Did he not tell the court about the defendant’s family? Did he not explain the remorse, the pointlessness of warehousing him for 18 years?

When a judge’s experience as a lawyer never touches criminal law, he would have no way of appreciating the implications of imposing outrageously long sentences. They are disconnected from reality, and defendants appear as one-dimensional vessels of evil, so that decades of imprisonment are shrugged off, rationalized by the simplistic embrace of “he deserved it.” He deserved something. Was “it,” was 18 years, what he “deserved”?

All the others sentenced, every one of them, is similarly worthy of a judge’s agony. Every one was a human being, had people who cared about them, did good things in their life as well as bad.  Somebody at sentence told that to the judge, but it flew around the bench and faded into obscurity.  After all, they’re just criminals, so who gives a damn. Eighteen years? That’s forever when it touches your life, but nothing when it’s some criminal’s life.

There are no second chances, Judge. That’s why you should have understood what it meant to lock a guy up for 18 years when you first imposed sentence. And if you can’t find it in you to agonize about the sentence you impose on every defendant, then you need to reconsider the propriety of your playing God with other people’s lives. Your insurance law background never prepared you to understand the harm you could cause.

It is good of you, Judge Underhill, to speak out against the callousness of the system. It’s unfortunate that you didn’t realize all this when you were given the first chance to not destroy a human being’s life. You should have gotten it right the first time.

13 thoughts on “A Second Chance, For the Judge

  1. Keith

    His insurance law background may not have prepared him for such mighty questions, but you’d think he may have learned something in “Philosophy, Politics and Economics” about how to treat others and the financial toll of decisions.

    1. SHG Post author

      Sigh. Is that what it looks like from the outside? You just made some judge spit coffee out his nose, and a lot of lawyers do an epic facepalm.

  2. bmaz

    You can’t get squat done in federal district courts already, where are the judicial resources to allow every incarcerated defendant a do over hearing going to come from??

  3. Maz

    And that’s why they don’t ask criminal defense lawyers to nominate judges: You’re clearly fixated on such secondary qualifications as experience in criminal law. Fortunately, those in the position to choose manage to keep their eyes on the prize:

    “[Underhill] also is a published author of some whimsy. With a friend, he parodied Yuppie values in the 1980s with a collection of updated rhymes: ‘If Wishes Were Saabs: Nursery Rhymes for Modern Times.’
    “Laughing, [Christopher] Dodd highlighted that section of Underhill’s resume.
    “‘So, in addition to being a legal scholar, he has a wonderful sense of humor,’ Dodd said, ‘which, as anyone who has served in public life will tell you, it’s very important you have that these days.'”

    But lest one fears Underhill brings nothing to the table beyond his sense of humor, though, we’re assured by a former US Attorney that “Stefan has the correct judicial temperament. […] He is thoughtful. He is intelligent. He is also practical and compassionate.”

    Most of all, though (and this sounds like the Stefan Underhill I remember from college, who always seemed hell-bent on achieving his next title, honor, or position primarily for how it would help him to win the one-after-next), he *really* wanted to be a judge — even though he “never dared to hope that dream was to ever come true.”

    OK, so it’s an 8-inch puff piece from the Hartford Courant and not his manifesto, but I can’t help but be wary of people who want to describe their goals in terms of *whom* they want to *be*, rather than *what* they want to *do*. I’m glad for Stefan that he got to be a judge; I’m ever happier he’s starting to realize the significance of what judges do. I hope it leaves him with more than the occassional sleepless night; I can think of no higher praise.


    (Speaking of praise, this is the sort of entry that leads people to say ridiculous things like, “This should be mandatory reading for anyone [nominated|asked to nominate someone] to the judiciary…” — as if anyone with the background, outlook, personality, and career required of either a nominator or nominee would ever dream of questioning his or her own fitness for the job. That said, it should be mandatory reading etc.)

    1. SHG Post author

      It wasn’t my intention to single out Judge Underhill, or to raise every issue that might exist with him personally. Indeed, to his credit, he wrote the op-ed, put his ass on the line and came out (kinda pretty much) on the right side. So for whatever flaws he may have (and who doesn’t), his effort he deserves appreciation. It’s far more than most have done or will do.

      1. maz

        No, you’re right; I think I got a little carried away. (Although the op-ed’s conclusion the solution to such problems is for Congress to give judges a mulligan *is* a little precious snowflake-y.)

        I had intended my criticism to be directed more toward Senator Dodd and whatever procedure/cabal is responsible for vetting potential appointees; it’s certainly not the nominee’s responsibility to highlight areas where his or her experience may be lacking. I was struck with how frequently news reports made note of Underhill’s qualifications for the position, though, only to have each qualification mentioned prove either a baseline requirement (I’m assuming there isn’t a pressing need for unintelligent or impractical federal judges) or irrelevant. Dodd *is* a lawyer, but given he was awarded his JD in 1972 and elected to Congress in 1974, I have to suspect he may not be the best, um, judge of what a judge should know, either….

  4. Jim Tyre


    You’ve raised the issue of whether the judge was qualified to impose the sentence, pointing to the fact that he had no criminal law experience before he became a judge. (He did become a judge 7 years before imposing this sentence, so likely this wasn’t his first dance, but that’s a side point.)

    Do you think that criminal matters in federal district courts should be assigned only to judges who have appropriate background and experience? (Whatever that may mean specifically.) If so, do you think that there should be other specialist judges in the federal district courts? In technology law, I see calls for specialist judges all the time, and those calls are not completely without justification. Not being a criminal lawyer, I’m not sure if there are similar calls in your field, though I wouldn’t be surprised. But they go against the very nature of how federal district courts work, where every judge becomes a generalist. Should federal district court judges be restructured so that litigants are at least somewhat assured of getting a judge who knows what he or she is doing?

    1. SHG Post author

      No. You’ve taken a huge leap from no experience to specialist. What is missing from many too judges is breadth of experience. They may know the one niche they practiced, but they’ve been cloistered, often in large firms, in very tiny slivers of law. They should know what it’s like to represent ordinary individuals. They should know what it’s like to have to get a memo done over night (as they so often demand) when you don’t have 20 associates to grind it out. They should have enough experience so that the defendants they sentences aren’t just cartoon characters but actual human beings.

      They don’t need to be specialists. If anything, they need to be less specialists.

  5. John Barleycorn

    Now why the heck didn’t I think of something like this?

    ♡♡♡ This “second-look review” should be available only to prisoners who are supported by their wardens. To minimize the increased workload on busy federal judges, each prisoner should be allowed only a single opportunity to seek early release and do so only after serving at least half of the sentence imposed (or two-thirds of a mandatory minimum sentence).♧♧♧

    You should follow up on that with a guest blawg post somewhere in the blawg-o-sphere Stefen and tell us more about these rules your sorrows will need when the leglislative support from under the hill springs forth.

    I like to make rules when drinking rum too. But I have to hand it to you, you guys from the nutmeg state don’t mess around with the nutmeg or rum do you?

    What could possibly go wrong? I love it! I knew I should have been adding more nutmeg to my
    hot butter rum all along.


  6. Chris

    I dont know if you have appeared before this judge, but to his credit he is one of the few “fair” judges in Connecticut. The other one being Judge Chatigny. Unlike other judges in CT, he doesn’t robotically recite the 3553(a) factors and wash his hands clean of the defendant. He routinely departs and tries to fashion sentences that he views as fair; fair being in the eye of the beholder of course. He has also granted more 2255 petitions in the past three years than all the other judges in the District of Connecticut for the duration of their “reign” combined. Judge Underhill was also vocal on the 2nd Circuit panel on US v. Corsey, a white collar case with no loss where a district judge in New York sentenced three elderly stooges to 20 years imprisonment. Despite the 2nd Circuit’s admonishment that the sentences were too high, on remand, she “departed” downwards and sentenced the defendants to 16 years; shortly after being re-sentenced/awaiting re-sentencing the defendants also departed, two of them died of heart complications. The case and its opinion were widely covered in the press, the ensuing death within weeks of being re-sentenced to 16 years in prison were not. The NY Times piece covers a period in 2006, when judges were still just getting used to being free of the Sentencing Guidelines and a 5K1.1 motion doesn’t really alter the crime.

    If you want to pick on judges, there are so many more cases you can pick out of your hat. Last year Judge Jeffrey Meyer, also of Connecticut, sentenced a dying man (Rober Lee Jr of Oxford, Connecticut) to 63 months in imprisonment for a white collar offense with approximately $1 million in losses. It was no secret that the man would die, he was rolled into sentencing on a wheelchair. Yet, Judge Meyer saw it fit to also berate the man at sentencing, just to make sure that before he leaves this world and meets his maker or decomposes into nothing, that the defendant knew what a horrible crime he had committed. Mr. Lee died 3 weeks later of incurable cancer. There are so many more.

    Its not that Judges lack training per se, its just that they have been thoroughly de-humanized (hundreds of cases as if the practice of sentencing makes them experts, it does not). Judges also know very little about what goes in prison (yes, almost all inmates can pull out a folder of certificates). Judges are intentionally naive: they think that prison is the only sentence that counts as punishment, and are more often concerned about getting the right headline instead of doing what’s right. You know this better than most: Judges stick their head in the sand and then blame someone else or look for a solution to a problem they helped create. But its not due to the lack of training. I don’t think any thing can train a person to calculate how many months or years of a man’s life should be destroyed (whether its the defendant’s fault or not).

    In another post, you had discussed Judge Chin’s sentence of Madoff to 150 years and Judge Chin was pretty honest about why he chose 150 instead of say 20, he wanted to get the right headline. And he did. The newspapers all carried his quote: “extraordinary evil.” Right, as if stealing was worse than murder or blowing up people/buildings. Judge Chin also got a promotion to the 2nd Circuit a few months after that….You talk about training, Judges are not just ex-lawyers. They are trained politicians. Always hoping they don’t hurt their chance of a promotion….

    1. SHG Post author

      This isn’t “picking” on Judge Underhill. But then, he doesn’t get a free pass when writing a Times op-ed because you like him. I’ve already made clear that this wasn’t a condemnation of one judge at all, and I’ve trashed a number of comment denigrating Judge Underhill, for missing the point as badly as you have, but in the opposite direction.

      When you write something publicly, it is subject to scrutiny. And your comment is brutally long. No one (including me) wants to read anything that long.

  7. Debra

    The previous comments may be pretty long and a tough read but it sums up Connecticut pretty well. Judges should get it right the first time but they just cant because Fill in the Blank with your guesses.

    If you look at all the other judges in Connecticut, for the most part, they are all former DOJ prosecutors, civil litigators, and so on. They all think prison is the place to reform, rehabilitate yadi yada. They basically recite the 3553(a) factors and you cant help but roll your eyes…..

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