Supporting Loved Ones - Character Letters

Supporting a loved one who is facing ongoing legal troubles is one of the most emotionally complex experiences we can go through. It’s a time marked by uncertainty, fear, and a deep, often helpless, longing to do something—anything—to make a difference. For many, that support comes through quiet presence, emotional encouragement, or navigating the legal system alongside them.

If your loved one was recently arrested and you’re unsure of what steps to take, you can start with this guide on how to prepare for court. But once the case enters the sentencing phase, one often overlooked—yet deeply impactful—way to show your support is by writing a character letter.

Writing a character letter is often far from easy. Putting into words your belief in someone—especially when their future may, in part, hinge on those very words—can feel overwhelming. Amid the uncertainty of criminal proceedings, it’s natural to feel confusion, guilt, frustration, or fear of saying the wrong thing. You may struggle with how to balance honesty with advocacy. Yet, character letters are a powerful opportunity: a way to lift your loved one out of the cold language of pre-sentencing reports and impersonal case files, and present them as the full, complex human being they are. In a system that can feel isolating and dehumanizing, a well-written letter becomes a meaningful act of connection, a chance to build a circle of support around the person on trial, and a reminder that they are more than their charges—they are someone who matters.

Addressing the Letter

To begin your cover letter, ensure that it is properly addressed to the judge assigned to the case. If you are unsure who the presiding judge is, you can find this information by accessing the case docket at https://eaccess.dccourts.gov/eaccess/home.page.2. Search using your loved one's full name to locate the correct case. The assigned judge’s name will typically appear on the docket. You can usually find the judge’s mailing address by searching their name along with the term "address." Use this information to format the heading of your letter appropriately. For example, a character letter addressed to Judge John Smith would begin as follows:

The Honorable John Smith*

Judge of the Superior Court of the District of Columbia 

Superior Court of the District of Columbia

500 Indiana Avenue, NW 

Washington D.C. 20001 

*Each judge’s official mailing address should be listed accurately on the court's official website. Be sure to verify the details before finalizing your letter.

Although your letter is addressed to the Court, it should be sent to your loved ones' attorney prior to sentencing.

Contents of the Letter

While typed letters are preferred, handwritten letters are also acceptable—as long as the handwriting is neat and easy to read. Regardless of format, ensure the font or handwriting is legible. Do not include your address, phone number, Social Security number, or any other personal identifying information other than your full name.

Begin your letter by introducing yourself and explaining your relationship to your loved one (e.g., family member, spouse, co-worker, neighbor, teacher, or friend), including how long you’ve known them. The most impactful character letters often start by stating who you are and what you do. Sharing relevant details about yourself can help establish credibility and strengthen your perspective.

You should also make it clear that you are aware of the charges your loved one is facing, and specifically name those charges in your letter.

To help guide your writing, I provide my clients' family members and loved ones with a few simple questions. If you’re able to thoughtfully address these within your letter, it can significantly enhance the impact of your statement during sentencing.

1. Is your loved one a thoughtful person? Do you know of any kindness that they have shown towards others? Do they have good relationships with their family and friends?

2. Are they a productive member of society? If so, why do you think so? Do you feel that they will be a productive and better member of society after this experience is over? If so, why do you believe so?

3. Do you believe that the offense is out of character for your loved one? What specifically makes you believe the offense was out of character for them? Is it unlikely they will violate the law in the future? Why do you think so?

4. Has your loved one been a hard worker? What specific examples do you have to demonstrate this? Is this a person who would show career promise after this case is over? Why?

5. Do you think that this experience has taught your loved one any lessons? What lessons and why?

6. If they served in the military, is your loved one proud of their military service? Were they generally a selfless person who put service to their country before self?

7. Has your loved one performed community service or otherwise donated their time, money, or performed other services for the community?

8. Is your loved one the kind of person who beats themselves up if they make a mistake or harm others? Have they been beating themself up and showing remorse as a result of this case? What specific examples do you have of your loved one showing remorse or beating themself up after making a mistake?

   
   

Further Details

Ultimately, the content of your letter is entirely up to you. Focus on what you believe is most important to share about your loved one. Use specific examples or personal stories that help illustrate the points you want to make. Reflect on your role in your loved one’s life, and how their actions or character have impacted you.

If you are a family member, center your letter around your loved one’s role in the family—for example, as a caregiver, provider, or emotional support. If you are a co-worker, employer, or business associate, focus on their contributions to the workplace, their professionalism, and their impact on the community. You may also wish to share that, despite their mistake, you would continue to work with or trust them—if that is genuinely how you feel.

It’s important to remember that character letters are not meant to excuse or conceal a crime. Rather, they are tools for the court to gain a fuller, more nuanced understanding of the individual being sentenced. There is no need to ignore or downplay the fact that your loved one has committed a crime. If you believe that their overall character remains strong despite the charges or conviction, don’t hesitate to say so.

Writing a character letter can feel overwhelming, but it can be a powerful and meaningful part of your loved one’s sentencing process. Please keep in mind that these are only suggestions to help guide you. If you or someone you know needs assistance at any point in this process, my team and I are here to help—don’t hesitate to reach out.

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www.myattorneywagner.com I 202.492.4659 I law@myattorneywagner.com

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