Bennett: The Art of Submitting Letters of Support

It is the exceedingly rare sentencing where I do not receive and read letters of support. I roughly estimate that I have read between 30,000 and 40,000 letters over the past twenty-three years. In one case alone, I read 107 letters.

For some very odd and unknown reason in our district, the Northern District of Iowa, these letters have always been referred to by everyone but me as “unsolicited letters.” That always makes me chuckle, because I, and my colleagues nation-wide, do receive unsolicited letters, but they start very differently than the letters on behalf of offenders. My favorite was years ago and received just before Christmas. Here is how it started:

Dear Judge Bennett,

I hope you nigger loving anti-American communist Jew lover have a nice Christmas.

It went downhill from there.*

So much for the digression. Judges, like all folks, are idiosyncratic, so my views on letters of support are simply my own views. I find that these letters can be exceptionally important and even crucial in framing a sentence that is sufficient but not greater than necessary. But more than half of the letters are next to worthless, and sometimes counter-productive.

I would think it is the role of the guiding hand of counsel to review letters and weed out the ones that are likely to be unhelpful or counter-productive. Here is a recent example from an eight-year-old son of a serial pedophile sex offender facing a substantial mandatory minimum.

Please send my Daddy home on probation. He is the best Dad in the world.

Really, I wonder? So here are my bullet points to separate good letters from poor and unhelpful ones. The letter should:

  • explain how, and how long, the person knows the offender
  • describe the qualities of the offender that the writer wants me to consider, with personal examples
  • acknowledge the offender’s wrongdoing (unless the offender is maintaining their innocence on appeal) and why they still have a positive view of the offender
  • discuss reasons for leniency with examples, e.g. her community service; his multiple tours of duty in Enduring Freedom
  • be factual where possible, giving reasons for mercy and not just a blanket plea for mercy (I already know the offender wants as little time as possible)
  • provide a factual basis for genuine remorse – if that exists
  • provide a factual basis for a plan when the offender is released on TSR (actually I have never received this kind of letter)

The letter should not:

  • tell me what they think the sentence (usually probation even when that is not possible) should be. I bristle at this and it often causes me to disregard or minimize the contents of the letter
  • minimize the offenders’ crime, unless there are specific facts that would support this
  • make the blanket statement that the offender has learned her lesson and doesn’t need to go to prison — but could explain why the offender has genuine remorse and specific reasons why she is unlikely to reoffend
  • tell me the offender will miss the graduation, birthdays, and weddings of children, etc. (I already know that and the offender wasn’t concerned about that when they were slinging kilos of meth)

In sum, I would be more impressed with a letter from a neighbor who knows the offender well than from some well-known politician who likely doesn’t know the offender but is writing as a favor to wealthy benefactor. It’s not the station in life of the writer that impresses me but how well the writer knows the offender that is important.

*Ed. Note: Lest anyone be offended by the language, this is what real judges face in the real world. It’s presented here unsanitized because this is how it actually happens in real life. If you find this offensive, then don’t become a federal judge. It will make you very sad.

15 thoughts on “Bennett: The Art of Submitting Letters of Support

  1. Christopher Van Wagner

    Judge Bennett, Thank you for this wonderful guidance. For years in defense, I have begged folks to follow a similar outline and format. Yet some letters trickle past me unseen, and when they do, I can invariably highlight the very words in such letters that will catch the judge’s glaring attention. The most painful one described my client’s 5-year effort to overcome addiction’s grip, which post-dated her dealing but predated her indictment. Then on the day before sentencing, from the judge’s chambers came a copy of a letter written by my client herself, over my advice. I circled this line and told her to expect to hear it read around in court: “… and now they are doing this to me.” Indeed, those were the first words enunciated when it came time for the late Hon. John C. Shabaz (W.D.WI.) speak. Fortunately, even the late judge had a heart and gave her a then-unusual downward departure, but not after singeing her ears with her own hand-written words.

  2. Billy Bob

    *Communist* is the part I like best. We’re all communists now. Only kidding! We have *only* 25% of the world’s prisoner population and the highest incarceration rate in the *civilized* world. This is not a *pretty picture*.

    If every judge would go on strike, or work slowdown at worst, imagine how much collateral damage could be avoided and how much better the world would be. Oh wait, you judges are already slow as molasses. Except when the issue of *contempt of court* rears its ugly head. ALL RISE!?! “Gentlemen will remove their headgear; mobile devices turned off. No texting.”

    Am surprised you pay attention to any *letters of support*. I would have thought otherwise. But I’m not a judge, nor would care to become one in a million years. Those who would be judges should be excluded automatically. However, the system is self-perpetuating. You cannot get it right, now matter how hard you try!

  3. Richard Kopf


    I once received a letter addressed to “KKKKopf.” I laughed so hard my hood fell off.

    All the best.


    PS Every point you make in this post I strongly second.

  4. Mario Machado

    Judge Bennett,

    I learned very early to tell the authors of these letters to avoid writing that the client “made a mistake,” especially when it involves a run-of-the mill healthcare conspiracy that involves hundreds of “mistakes” made over several years. People tend to minimize these mistakes, even after being told not to do so, and you’re asking for a benchslap if you don’t use your guiding hand to prevent said letters from ending up in Judge’s chambers.

    My favorite is when people bring 20 letters using the same boilerplate language, same font, etc. In the words of John McEnroe, “You cannot be serious!”

    Clients quickly learn who their real friends are when they ask for a letter. Some say “just write it for me and I’ll sign it,” while others won’t even respond. Makes me think of a quote by the Joker from The Dark Knight: “When the chips are down, these … these civilized people, they’ll eat each other.”


  5. Pingback: Sentencing — Court-Martial Trial Practice Blog — October 9, 2017

  6. Mark W. Bennett

    Dear Billy Bob,
    I can say that I have read every single letter in support of an offender. I read them carefully, because they have the potential to unlock important characteristics of an offender that, for many reasons, aren’t fully developed in the excellent pre-sentence reports we receive. Some are exceptionally moving and provide me with insight to ask questions of an offender if they allocute. I do give the offender a 5th Amendment oral Miranda tyoe warning that they do not have to allocute and that I will not hold it against them in anyway if they exercise the most important right we all have and that is the right to remain silent. I repeat that warning if I ask questions. The one-on-one interchange with an offender is one of the things that has made my work priceless to me.

  7. Mark W. Bennett

    Oh, Mario, I did have the “form letter” problem in a large white collar fraud case with 107 letters most of which had virtually identical key phrases in them. I requested an explanation from the defense lawyers prior to sentencing and they did truthfully respond that a form letter had been sent to prospective letter writers by as I recall either the spouse pr a close friend. Doing it this way is not very helpful. Actually, I would rather hear from 3 or 4 live character witness that the AUSA can cross examine and that I can ask question of than receiving 107 letters. Because potentially depriving someone of their liberty is the single most important thing I do a judge should never be in a hurry in a sentencing hearing. That’s why a let a white collar fraud defendant allocute for 7 hours over two days. while I felt a little like a U.S. Senator in a filibuster it was important to both justice and the perception of justice that he said his piece – which ultimately hurt him because he denied all responsibility, even for the 17 counts he plead guilty to and the 4 counts a jury found him guilty on.

  8. Sol Wisenberg

    Thanks, Judge. This is a worthy companion to your outstanding (and entertaining) article on allocution a few years ago in The Champion. I still give a copy of Heartstrings or Heartburn to all of my sentencing clients. I imagine that you are also troubled by letters stressing a defendant’s charitable contributions when you are about to sentence him/her for some massive embezzlement.

  9. Mark W. Bennett

    Dear Sol,
    A few years back I was leaving the bench after an offender give a world-class allocution that was matched by my huge variance. As I was walking off the bench I noticed the offender had his hand up so I called on him. He asked what I thought about his allocution and I told him it was one of the best I have ever heard. with a sly grin he added “That’s because I read your article.” I chuckled to myself on walk back to chambers wondering if I had been had or not. No way to know so I just let it go, I like to give almost everyone I meet in life the benefit of the doubt. I find it’s a better way to lead my life. I have given weight to charitable contributions when I am sure they ere not the fruits of the fraud. After all its easier to give away money one did not earn. Best

  10. JAV

    Only wish I had some more advice like this the one time I wrote such a letter. I could only figure out so much from a Google search.

  11. B. McLeod

    AtL had an annual “holiday cards” contest, and this post shows how comparatively intriguing a “holiday letters” contest on this site could be. Just get regular posters to offer up five or six of these rare jewels, and let readers vote on which is best (and/or worst). How about it, Admiral Greenfield? You could be missing a real opportunity to grow the fan base here.

    1. SHG

      So you’re saying SJ is too practical, thoughtful and substantive and should become more hip, fun and cool like ATL?

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