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“To Justin, Forest, and the entire team, thank you from the bottom of my heart. You made an incredibly difficult time for our family manageable and gave us hope when we needed it most.”
How do you write a letter to a judge for sentencing?
Tell one story you witnessed. Michael Kestler's family started their letters the week his son's case began, and each writer described what they had seen firsthand. Avoid the five drafts we see most: the résumé, the retrial, the request, the everything letter, and the letter about the writer.
Facts | |
|---|---|
Who | A father writing for his son |
Referral | Matt Bowyer, a golfing friend |
What the family built | Personal narrative, character letters, a record of steps taken before sentencing |
Outcome | Not disclosed by the family; Michael called it "the best possible outcome under the circumstances" |
Someone you love is facing a federal judge, and you've been asked to write a letter. You've opened a blank document three times. Each time you typed "Dear Judge" and stopped.
Michael Kestler knows that page. His son was facing the prospect of serious prison time, and Michael wanted to do something that would actually help.
He didn't find us through a search. Matt Bowyer, a golfing friend, told him to call. Matt had prepared for his own federal sentencing with our team before he served his time at Lompoc Federal Prison Camp. Michael called.
"My family was incredibly fortunate to have been introduced to them during one of the most challenging times of our lives. What could have been the worst-case scenario for our family turned into the best possible outcome under the circumstances."
Start the week the case lands
"My son was facing the prospect of serious jail time, but with Justin's leadership, we immediately put a comprehensive plan of action into motion. This, coupled with a lot of hard work, helped us demonstrate that this incident was completely out of character, a one-time, foolish mistake."
The word that matters there is immediately. The Kestlers didn't wait for a hearing date. They started on a personal sentencing narrative, a plan for the character letters, and a record of the steps taken before sentencing.
Letters take longer than anyone expects. Writers need time to remember something specific, get it on paper, and rewrite it. The defense attorney needs time to read every one. A letter written the weekend before the hearing reads like it.
Who writes what
The narrative belongs to the person being sentenced. It is his account of his life, his conduct, and how he got to that courtroom, in his own words. If a parent writes it, it stops being his.
The letters belong to everyone else. Each writer speaks only to what they saw and knew firsthand: how long they've known him, what they know about the case, and why they're writing.
The Kestler family members supplied their own experiences and their own words. Our team helped organize the material and get it ready for review with defense counsel.
Five letters we see every week
Most first drafts fall into one of five patterns. If yours does, it can be fixed.
The résumé. Titles, awards, years of service, board seats. The judge already has his biography. Cut the list and tell one story: a day you were there, what he did, what you saw.
The retrial. The writer argues the facts of the case or explains why the charges are unfair. That argument belongs to the defense attorney, and a letter that makes it suggests the family hasn't accepted what happened. Say plainly that you know why he is in court. Then write about what you've seen.
The request. "Please give him probation." The writer asks for a specific sentence. The judge decides the sentence. Your job is to tell the judge something about the person that the file can't.
The everything letter. Four pages, a dozen anecdotes, no single moment the judge will remember. One page with one story will be read more closely than four pages with twelve.
The letter about the writer. Paragraphs about how much the family will suffer, with nothing the writer has seen the defendant do. If the hardship is real, make it specific. Who depends on him? For what? How often? What happens to them while he's gone?
A letter that works usually holds four things. Who you are and how long you've known him. A plain sentence acknowledging why he is in court. One or two moments you witnessed. What you've seen him do since the case began.
Working alongside the lawyer
Michael put it this way:
"I firmly believe that without Justin and his team's guidance, leaving this solely in the hands of our attorney would not have yielded the same positive result."
Defense counsel handles strategy, filings, and advocacy, and decides which letters go to the court. A family can do the work a lawyer has no time for: finding the right writers, helping them remember, and getting every letter to counsel early enough to matter.
Send your letter to the defense attorney, not to the judge.
"The best possible outcome under the circumstances"
Michael did not share his son's charge, guideline range, or sentence. He described the result in his own words, quoted above, and closed his review with this:
"To Justin, Forest, and the entire team, thank you from the bottom of my heart. You made an incredibly difficult time for our family manageable and gave us hope when we needed it most."
Tonight, before you write "Dear Judge" again, write one paragraph about a single day you saw him at his best or handling something hard. Name the day, the place, and what he did. Then work through our free course on character reference letters, which walks you through building the rest of the letter around that paragraph.
Thank you,
Justin Paperny
Written by
Justin Paperny
Founder White Collar Advice