How To Write (Or Solicit) A Good Letter Supporting A Defendant At Sentencing

This week various political figures took some abuse for writing letters seeking leniency in the sentencing of former House Speaker Dennis Hastert, who got a 15-month sentence for monetary transactions designed to conceal that he was paying off victims of sexual abuse.

I've argued before that if you write a sentencing letter in support of a famous (or notorious) person, the media will report on it in an insipid and sensational way. That's inevitable, and media reaction isn't my focus. My focus is suggesting how to write a letter that furthers the best interests of the defendant and is most likely to move the judge towards a better result.

With that in mind, here are some rules:

This letter is not a vehicle for you to express yourself. A letter supporting a defendant is not an opportunity for you to posture, work out issues, or express yourself artistically. It is an opportunity to help the judge see the defendant as a human being. If you cannot stop yourself from making your letter about you instead of about the defendant, or if you find yourself focusing on how the letter makes you sound, please don't write the letter.

Nobody cares what you think about this case or the criminal justice system. Now is not the time to say that the criminal justice system is unjust or should be spending resources on other things or how far worse criminals get away or how this shouldn't be a crime or this is politically motivated. Go write that shit on your LiveJournal. It will annoy the judge.

For these purposes, the defendant is not innocent. Most likely the defendant pled guilty. Or maybe he or she was convicted by a jury. Either way, the judge is starting from the premise that the defendant is guilty. Appeals and habeas corpus motions — or, maybe, attorney arguments about residual doubt — are the place for discussions of innocence. A sentencing letter isn't. "I know he didn't do it" and "this must be a mistake" dramatically undermine a defendant's statements of contrition in plea cases, and simply annoy the judge in jury verdict cases. If the defendant has done his or her best to accept responsibility and covey their regret and you come in and write "I've talked to him and I know he didn't do it," you are undermining the defense. It's not persuasive.

Don't bother if you don't know the defendant fairly well. A good sentencing letter isn't like a letter of recommendation that a professor writes about one of the 150 students in a frosh cattle-call course. It's something you write if you know the person — if you have a connection to them. Letters by mere acquaintances are worthless at best and damaging at worst.

When you praise the defendant's character, bear in mind they are being sentenced for a crime. The core idea "I was shocked by this case because I know the defendant to be a good person" is okay, expressed carefully. So, for instance, if your friend is being sentenced for structuring monetary transactions to hide the fact he's paying off people he sexually abused as kids when he was a coach, saying "[w]e all have our flaws, but Dennis Hastert has very few" is appallingly tone-deaf and probably hurts the defendant. Praise of the defendant can't ignore the present circumstances, or it seems uninformed or stubbornly blind. "Defendant's behavior towards me has been so kind and decent that these serious charges were devastating" is the right tone.

Don't minimize the crime. Why do I have to tell you this? Don't suggest that the crime isn't a big deal. Even if it isn't. That's for the defense lawyer to argue, not you. You're going to undermine the defendant's attempt to show contrition.

Don't attack the victim. You utter moron.

Don't talk about your yacht. When you're talking about how well you know the defendant and how you and the defendant have interacted, avoid emphasizing things that highlight the defendant's life of privilege and/or power. First, it sounds like you're bragging, which is obnoxious. Second, it sounds like you are implying that rich or powerful people should get lower sentences, will will antagonize the judge. Third, it tends to make the defendant look worse: if he or she had so much, why did they do this? Downplay it.

Humanize the defendant, preferably with private conduct. It's fine to talk about how a defendant has led a life of public service. But the best stories to tell are the ones about how the defendant acted when nobody was looking. Some of the most powerful letters are about the defendant's small, private acts of humanity, compassion, and decency. You are, after all, asking a judge to see this defendant as an individual human being rather than as a statistic — to exercise mercy. What better way that to tell a story about such mercy exercised by the defendant? The letters I like best aren't the ones about how my client paid to attend a charity gala every year. They're the letters that tell the story about how the client visited the company's receptionist in the hospital and took her whole visiting family out to dinner, or about how he or she helped a stranger, or how he or she showed private kindness. "This Congressman supported the Family Leave Act" is not nearly as powerful as "when my mom died Bob stayed up with me all night and drove me to the funeral home and sat with me while I handled her affairs."

Don't tell the judge what to do. Some lawyers ask letter-writers to ask for a specific sentence, or to ask explicitly for leniency. I don't. I don't think it's effective. The judge knows what the defense is asking for — the defense lawyer is arguing it. Parroting the defense lawyer's talking points makes the letters sound too orchestrated. For most letter-writers, you're asking the judge to consider the type of person you know the defendant to be. The right tone is "I ask you to consider these experiences in sentencing my friend" or "when you consider the crime, I ask you also to consider these things my friend is done." The exception is a close family member who is directly impacted by the sentence — "I don't know how we can keep the house or keep the kids in school if my spouse goes to prison."

Not every lawyer agrees with these rules. But I find them more effective and the judges I've talked to find such letters more persuasive.

Last 5 posts by Ken White


  1. P. Ross says

    In the paragraph "Humanize the defendant" I think you may have accidentally reversed the meaning of your second sentence.

  2. David says

    Another tone-deaf thing you could do would be to praise a guy who just admitted to sexually abusing kids he coached, for being a good mentor to the kids he coached. Even when you're not outright denying the defendant's guilt, you still need to make sure it's part of the premise of your statement.

    (This message brought to you by my constant facepalms while reading the Hastert family's letters)

  3. Jeff says

    The fact that all of these aren't utterly, inarguably obvious to everyone who might plausibly be asked to write such a letter is disturbing, appalling, and likely hilarious to everyone except the defendant and the judge.

    Yikes, Ken!

  4. Richard says

    [Judge] Hmmm, I'm thinking six months, but let me read these letters to see whether they change my mind.


    [Judge] The defendant will be imprisoned for the rest of his natural life, in solitary confinement, with Justin Bieber music playing on repeat.

  5. Daniel Weber says

    Lots of things that are normally obvious when sitting comfortably in front of a computer become less so when facing the prospect of a friend going to jail.

    I'm reminded of Clark's post here about how people think "how can confessions be false? Why would an innocent person confess?"

  6. SirWired says

    re: The letter praising Hastert's advocacy prowess on behalf of collegiate wrestling vs. Title IX (From, I believe, the U of IL wrestling coach) … I remain utterly baffled as to what the author thought that was supposed to accomplish.

    I could understand pleading for a lenient sentence so that said convict could get back to a rich life of public service, but collegiate sports are not exactly a group bereft of political power necessitating Hastert's earlier release.

  7. TooManyJens says

    Also, defendants, consider not soliciting letters of support from someone whose brother you sexually abused.

  8. Matthew Cline says

    If I, whom am not at all involved in the case, were to a letter to the judge involved saying "Hastert must be kept out of prison, to prevent the Prophecy from being fulfilled", how much trouble would I be in?

  9. Dawnsfire says

    Is there any chance these people secretly hated him and wanted to do as much damage as possible? I read some of these letters and that was my first thought.

  10. says

    I'm puzzled by the process here. Shouldn't the defense team have pulled the more damaging letters from their filing? Or suggested a rewrite?

    Then again, I'm also puzzled by someone who is asked to write a letter for a defendant who doesn't immediately call the defense lawyer and ask for advice. "What's the message I should be conveying? Is it that a long sentence would be a travesty of justice? Or is it more like asking the judge to please remember that for all his crimes, my friend still has some good in him?"

    Seriously, shouldn't there be some editorial influence here?

  11. says

    It's odd to me that a judge would put much weight on these letters. I understand that you want to do everything you can to help a friend, but it just sounds weird that a letter from someone with no connection to the trial or the judge could influence his/her opinion.

  12. King Squirrel says

    Was asked to write a letter for a cat sentenced to death once.

    He was a quiet, friendly bookstore cat who was cornered by two small children who wanted to "play with kitty" – dad was snapping pictures of the cute. Then they acted like small children.
    No serious injuries but, as the saying goes, bystanders were surprised by the copious amounts of blood.

    Don't remember what I wrote, but did try hard to avoid attacking the dad. Cat ended up banished from the bookstore on pain of death, but lived.

  13. JRM says

    I've been a crime victim and a prosecutor on crimes with letters written. Live performance counts, too.

    Let me add:

    Do not snicker at victim's impact statement.

    Do not accuse the crippled woman of faking her injuries. (You're right, she was out of the wheelchair until they removed the screws and plates.)

    Do not accuse the widow of overstating her loss.

    Or, you know, do that. It infuriates the victims and the prosecutor and maybe the judge. Who am I to stop you?

  14. Allen says

    Shoot, This post led me to go back and read my first and only defendant character letter from 5 years ago. It was all good until I said that it would be a shame to let justice fall down so harshly and recklessly on the defendant. Thanks for lesson I hopefully won't ever have to use.

  15. mythago says

    I am guessing writing such a letter on your firm letterhead, to emphasize your own importance and perhaps attempt to extend your influence to the judge's decision, is also right out?

  16. OrderoftheQuaff says

    Dear Judge Flapjack,

    At the outset I would like to acknowledge the terrible crimes of which my friend was convicted, even though it is undisputed that he wasn't actually present for any of the murders. I've known him for a long time and have personally witnessed him fostercare and find good homes for an abandoned litter of eight kittens. I submit to you that he has adequately paid his debt to society. Because he has raised himself up from nothing to become a cultural icon, I can assure you that he will not become a burden to society if you order his release, because he will be able to sufficiently monetize his notoriety into something, possibly a line of casual menswear. For the foregoing reasons I urge you to order the release of Charles Manson in the interest of justice.

    The Quaffer

  17. Encinal says

    A letter supporting a defendant is not an opportunity for you to posture, work out issues, or express yourself artistically.

    How naive of you.

    Your other points presume that the writer's terminal goal is to reduce the defendant's sentence, and inform the writer how to accomplish that goal. But if the writer's terminal goal is to promote their own interests, and reducing the sentence is merely a means to that end, then informing them that that's not what it's "supposed" to be for, doesn't really make sense.

    But the best stories to tell are the ones about how the defendant acted when nobody was looking.

    That doesn't really make sense, either. I suppose you could tell a story about a time when the defendant thought no one was looking, or when you think the defendant thought no one was looking, but obviously you can't tell a story about how the defendant acted when no one was looking. Goodhart's Law kinda applies here.

    @Daniel Webster

    I'm reminded of Clark's post here about how people think "how can confessions be false? Why would an innocent person confess?"

    Why would a guilty person confess? I fail to see any a priori reason for thinking that a confession is Bayesian evidence for guilt. If anything, one could make an argument that innocent people are more likely to confess.

    @Matthew Cline

    If I, whom am not at all involved in the case, were to a letter to the judge involved saying "Hastert must be kept out of prison, to prevent the Prophecy from being fulfilled", how much trouble would I be in?

    "I" is the subject of the verb "involved", so the subjective form "who" is called for.

  18. YoSup says


    I was amazed at the point about him protecting the wrestling team. The fact that he fought to preserve the program that was delivering him children to abuse isn't a good look.


    It should be "who", but that's because it's the subject of "am", not "involved". And "I" is the subject of "were", not "involved", but the function of "I" is irrelevant to the case of "who". In "they told John, who hadn't yet heard", the fact that "John" is the object of "told" doesn't change the fact that "who" is subject of "hadn't" and takes the nominative case.

  19. I Was Anonymous says

    @Zem, Admitting you like ponies is a good reason for the death penalty.

  20. James says

    I guess another thought is, if you're asking for leniency against someone who has sexually molested children, but is being sentenced for a relatively minor crime instead because while the statute of limitations and/or ability to prosecute effectively the serious and heinous crime we *know* he committed, here's a strategy you can take:

    Just don't.

    Just put the pen down and don't. Go outside. Read a book. It's early may and was the middle of april: take your family to the beach and fly some kites. Maybe, I dunno, get some work done and hold a judicial nomination hearing for Merrick Garland like the Constitution says you're supposed to.

  21. ChrisH says

    I still don't get the whole "statute of limitations"* thing when it comes to shit like this.

    * I'm a Brit. I'm pretty sure that we don't do this.

  22. James says

    There's a lot of good reasons for it. I don't know if that's EXACTLY what happened here because I'm no lawonomer (I'm more into lawology myself), but another aspect could simply be that when the evidence grows stale and the material witnesses have spent 20 years living with it, it's really hard to make a case. "It's been 20 years he's probably misremembering" is a fairly easy way to demonstrate "reasonable" doubt.

    On the other hand, you can definitely slam him with a felony for what he did. And besides, he's had a stroke and a bloodclot in the last year, he's not long for this world. As you brits say: good riddance to bad rubbish. Or maybe that's just ozzies.

  23. Tradegeek says

    I had to laugh when I saw two of Jack Abermoff's cronies wrote a letter on behalf of Hastert. Tom DeLay being one of them.

    If Johnny Manziel agrees to a deal on his domestic violence charge, I wonder who will write letters on his behalf?

    I'm guessing OJ Simpson and Ray Rice, given that Ike Turner died some years back.

  24. Søren Kongstad says

    I've always found the US justice system quaint.
    In Denmark we do not have character witnesses. Whether you're an asshole or a saint shouldn't have any impact on your trial, or eventual sentence.
    Another thing is the oaths.
    In Denmark it's illegal to lie in court, no oaths are necessary or called for.

  25. sporaderic says

    I'm late to the party, but it seems like it'd be easiest to just go with "I know where you live." Is there some sorta subtle 'gotcha' faux pas in there that I'm missing?

  26. KeithB says

    Soren Kongstad:
    The US has laws against Perjury.

    What happens when your testimony contradicts earlier statements? In the US, we have Oaths as a way of saying that you really need to tell the truth now, or something bad will happen to you, and we are going to assume that what you say under oath is the true version, whatever else you said not under oath does not count.

  27. Mike Schilling says

    'I've known Dennis for many years, and one thing I can say for sure about him is how fond he is of children."

  28. staghounds says

    If it is rational, talk about the defendant's plann which he had better have.

    . "Give him another chance, he has learned his lesson" is not really effective. Talk about what has or will change in the defendant's life that makes him less likely to commit crimes again. You are asking the judge to take a chance on a stranger, give him a reason and a vision of the future that is different from this character coming back again.

  29. calwatch says

    Interestingly thanks to the Brock Turner case, we now have a dump of all the support letters written on Turner's behalf:

    The teachers, counselors, and those who were a generation above Turner seemed to have been given directions similar to yours above, sticking to what they know and not casting aspersions on the victim or denying the crime happened. Turner's peers, unfortunately, failed in the majority of the instances, and as such have been subjected to (deserved) public ridicule.