Can Character Reference Letters Help at Federal Sentencing?

“No man is an island, entire of itself.”

John Donne, Devotions upon Emergent Occasions (1624)

Federal prosecutors asked for 15 years in prison. The judge imposed three. During sentencing, according to Casey Crowther, the judge discussed character reference letters describing his roofing business, hurricane recovery work, and years coaching youth football.

Casey had pleaded guilty to mortgage fraud and been convicted at trial of misusing Paycheck Protection Program funds. The 14 letters prepared before sentencing gave people who knew him an opportunity to describe experiences that had nothing to do with the criminal charges.

“The judge brought up the letters at my sentencing hearing. He said it was clear that this case was out of character for me.”

A Fourth-Generation Roofer Facing Federal Prison

Casey grew up around the roofing business in Fort Myers, Florida. He learned the trade through an apprenticeship with his family's company before starting Target Roofing, which eventually employed 220 people. His crews worked throughout the region, including repairing damaged roofs after hurricanes. Outside work, Casey coached youth football and spent years with children and their families.

His federal cases involved two different offenses. He pleaded guilty to mortgage fraud after providing inaccurate information on a mortgage application. A jury also convicted him of misusing funds from the Paycheck Protection Program, which Congress established to help businesses maintain payroll during the COVID-19 pandemic.

Casey faced the possibility of a lengthy federal prison sentence. His defense attorneys were handling the criminal proceedings, and he had been working with them for approximately ten months when he discovered White Collar Advice on YouTube.

He contacted us about a month before trial because he wanted to understand what could happen if he went to prison.

“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.”

We introduced Casey to Michael Santos, who had served 26 years in federal prison. Michael interviewed him about his business, family, personal history, and experiences with alcohol use and addiction in his family. They also discussed what Casey might encounter in prison.

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

Fourteen Letters From People Who Knew Him

As sentencing approached, we helped Casey prepare 14 character reference letters. We contacted people who knew him through Target Roofing, hurricane recovery projects, and youth football. We asked them to describe what they had personally witnessed rather than offer general statements about his character.

A person who worked alongside Casey after a hurricane could describe how he responded when homeowners needed repairs. Someone from the roofing business could discuss years of working with him. Parents and fellow coaches could describe what they remembered about his involvement with their children.

Those accounts gave the writers something specific to tell the judge.

During an interview with Michael Santos, federal Judge Mark Bennett explained that he had read an estimated 30,000 to 40,000 character reference letters during his judicial career. He recalled one case involving 93 letters, many repeating language from the same template. The number of letters did not make them persuasive.

“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.”

Judge Bennett also offered advice about what writers should avoid.

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

Casey's letters described his work and relationships. They did not need to instruct the judge what sentence to impose.

Federal Judge Stephen Bough made a related point during our interview about sentencing preparation. He recalled receiving 67 character letters in one case and warned, “Don't bury the judge in 50 letters that they can't read, and then they start skimming over them.”

Casey submitted 14. The value of those letters came from what the writers knew about him, not the number collected.

The Government Requested 15 Years. The Judge Imposed Three.

At sentencing, prosecutors asked the court to impose 15 years in federal prison. Casey's attorneys represented him and presented their arguments to the judge.

According to Casey, the judge discussed the character letters and the community work they described. He remembers hearing the judge refer to his hurricane recovery activities and involvement with youth football. The comments meant a great deal to Casey, particularly because reporters were present 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.”

The judge imposed three years in federal prison.

Casey had prepared the letters with our team while his defense attorneys handled the case. He left sentencing knowing he would serve three years and that the judge had discussed accounts from people who knew him long before the criminal proceedings.

Six Days Before Entering Federal Prison

Six days before his surrender date, Casey spoke with our team again. His trial and sentencing were behind him. He was preparing to leave his family, roofing business, and community to serve his sentence.

Michael had discussed prison life with him, including the Residential Drug Abuse Program, known as RDAP. The Bureau of Prisons determines eligibility for that program and any associated benefits. Casey understood that he would have to adjust to an unfamiliar environment, follow prison rules, and begin planning for his eventual return home.

“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. I want to use my experience and skills to make a difference in the lives of others.”

He had spent years running a roofing company and coaching football. Now he was preparing for three years in federal custody, with hopes of using his experiences to help others after release.

Who Could Write a Character Letter for Your Federal Sentencing?

Casey had people who knew him through work, hurricane recovery, and youth football. Their letters described experiences they had shared with him, giving the judge information about his life beyond the criminal charges.

If you're facing sentencing, consider who has known you long enough to describe something specific. A longtime employee may remember how you handled a difficult situation. A customer may recall a problem you helped solve. A coach, teacher, relative, or volunteer coordinator may know something about your life that does not appear in the government's account of the offense.

Ask what those people could write from firsthand experience. Your defense attorney can help determine which letters are appropriate and how they should be submitted.

White Collar Advice helps clients prepare character reference materials, personal narratives, and plans for federal prison while their defense attorneys handle the legal case.

Schedule a complimentary consultation to discuss your circumstances and what you can begin preparing. You can also call or text 949-799-3277.

Thank you,

Justin Paperny