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Client Case Study4 min read

Character Reference Letters for Federal Sentencing

Casey Crowther's 14 character letters came from his roofing crews, his hurricane jobs, and the youth football field. Prosecutors asked for 15 years. The judge imposed three.

Justin Paperny

Founder White Collar Advice · October 20, 2026

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“Invested the time to build a record that took the totality of my life into consideration.”

Can character reference letters help at federal sentencing?

Make a list of people who watched you do something before your case began. Skip the ones who would only vouch for your name.

Casey Crowther's list came from three places: his roofing crews, his hurricane jobs, and the youth football field.

He was a fourth-generation roofer from Fort Myers, Florida. He learned the trade as an apprentice in his family's company, then started Target Roofing and grew it to 220 employees. His crews repaired roofs across the region after hurricanes. Away from the business, he coached kids in football and got to know their families.

We contacted people from all three groups and helped Casey assemble 14 letters. Each writer described something they had seen him do.

What a judge does with 93 letters

Federal Judge Mark Bennett told Michael Santos he had read somewhere between 30,000 and 40,000 character letters. He remembered one case with 93, many built from the same template.

"I'd much rather have a letter from a street sweeper or a janitor that has known the individual for, you know, maybe more than ten years or maybe most of their life than a letter from a state senator or a United States senator that's clearly writing it as a favor to the family."

What he wanted from each writer:

"Tell me how you know the person, what their characteristics are, and then let me decide how that fits into an appropriate sentence."

Spread your letters on a table before you ask anyone else to write. Count how many open with the same sentence.

A month before trial

Casey called us about a month before trial. He had spent roughly ten months with his defense attorneys and had found our videos on YouTube.

"It's scary not knowing anything about the process. Listening to Justin made me feel better. He put me in touch with other people with similar charges and circumstances. Once I knew more, the process became much easier."

He pleaded guilty to mortgage fraud for putting inaccurate information on a loan application. A jury convicted him of misusing Paycheck Protection Program money.

We introduced him to Michael, who served 26 years in federal prison. Casey talked with Michael about his drinking and about addiction in his family.

"Michael survived such a long sentence. He had it ten times worse than me, so his positive attitude made a huge impression on me."

Reporters in the courtroom

Prosecutors asked for 15 years. The judge imposed three. Reporters were in the courtroom.

"The judge brought up the letters at my sentencing hearing. He said it was clear that this case was out of character for me. The judge gave me a downward departure on my sentence based on the community service work described in the letters. Also, the media in the courtroom got to hear about me from another point of view."

Six days out

We spoke with Casey again six days before he surrendered. Michael had walked him through prison routines, including the Residential Drug Abuse Program.

"I am ready to go to jail and optimistic about the future. I want to give back and help other people stay out of trouble."

Bring your list of letter writers to our next webinar, and we will tell you who is missing from it.

Thank you,

Justin Paperny

Written by

Justin Paperny

Founder White Collar Advice