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What Judges Say About Character Reference Letters

As we have discussed in previous articles, when facing sentencing, defendants need to pursue every possible avenue to influence the outcome of their case. One powerful tool in their arsenal is the character-reference letter. These letters, written by individuals who know the defendant well, can provide valuable insights into the defendant's character and the impact they have had on others.

The Quantity Conundrum:

Michael Santos from Prison Professors is a pioneer in the self advocacy and justice reform space. He has spoken with a number of federal judges on a range of topics including character reference letters.

Judge Mark Bennett, a seasoned federal judge, has offered valuable advice based on his experience sentencing over 4,000 individuals. One of his key insights is that while character-reference letters can be a potent asset, submitting an excessive number of them may not always be beneficial. We see on on average, defendants submit between ten and twenty character-reference letters. However, going overboard, as in the case of one defendant who submitted 100 such letters, can be counterproductive.

Judge Bennett emphasizes the importance of quality over quantity. Judges prefer to read letters from individuals who have deep, personal connections with the defendant rather than hundreds of acquaintances. A letter from a longtime family friend will likely be better for you than a letter from a state congressman who you met once at a fundraiser. Additionally, a flood of similar-sounding letters with similar stories can dilute their impact and may even work against you.

The Power of Authenticity:

Authenticity is paramount when crafting character-reference letters. Judges look for genuine information from individuals who truly know you. These letters should provide specific, meaningful details that reveal you as an individual rather than generic statements of goodwill.

Instead of generic praise, judges want to hear stories that highlight your contributions to the community or the lives of others. These stories create a lasting impression and can sway the judge's decision in the defendant's favor.

The Impact of Stories:

Judges, like everyone else, respond to stories. A compelling narrative can be a game-changer in a sentencing hearing. Take, for example, a case in Judge David Carter's courtroom, where a defendant faced a substantial prison sentence for a $6 million fraud offense. Despite guidelines recommending a lengthy sentence, the defendant's post-conviction rehabilitation and character-reference letters transformed the outcome resulting in a significant downward departure.

What set these character-reference letters apart were the stories they told. Rather than offering generic compliments, they painted vivid pictures of how the defendant had positively impacted the lives of others. Judge Carter and the prosecutor were moved by these stories, ultimately leading to a more lenient sentence.

The Changing Landscape of Sentencing:

Before the 2005 landmark U.S. Supreme Court decision in U.S. v. Booker, judges did not consider a defendant's personal characteristics in sentencing. However, the Booker decision expanded the scope of sentencing factors, requiring judges to consider factors like the defendant's history, needs, and mitigating circumstances. This change placed greater importance on character-reference letters as a means to provide valuable insights into the defendant's character.

Strategic Character-Reference Letter Writing:

To make the most of character-reference letters, you should be strategic in your approach. Make sure the letters, as a collection, weave a narrative that will influence a judge to be lenient. These are a few of the tenets we have seen be successful at sentencing:

  1. Serve a Specific Purpose: Character-reference letters should help judges understand the you as an individual and the totality of your life.

  2. Tell a Story: The letters should provide specific examples of your character through anecdotes and stories at various points in time (i.e. examples from one year ago, three years ago, five years ago, etc.)

  3. Highlight Value to Society: Emphasize how the you have positively contributed to the community or the lives of others when no one is looking. Yes, being on the board of a foundation or non-profit is great but what have you done when there was no accolades for you?

  4. Be Consistent: Ensure that all the letters portray a similar story and align with the overall mitigation strategy presented during the hearing. You don't want a judge to read a letter and wonder are we talking about the same person?

  5. Show Remorse: Even if you are innocent of the crime, you did something wrong to be here - someone you associated with or some gray ethical area you crossed. No one wants to hear how the system is broken and corrupt. All people want to hear is that you are sorry and why this is never happen again.

  6. Worthy of Redemption: You need to demonstrate how this event has changed you at the core and how you are committed to living as a law-abiding citizen.

A Judge's Need for Backstory:

Judges often express their frustration when they lack essential information about the defendant. Providing your backstory is crucial for when striving for leniency. Judges want to understand the context and circumstances that led to your actions, and character-reference letters can help fill in these gaps.

A Comprehensive Mitigation Strategy:

The goal of a comprehensive mitigation strategy is to show why the defendant is a worthy candidate for mercy. Character-reference letters play a vital role in achieving this goal by shedding light on the defendant's character and contributions to society.

Avoiding Pitfalls:

Learn from the mistakes of others. In the high-profile case of Danny Masterson from That 70's Show, his team submitted approximately 70 character reference letters including from high profile individuals like Aston Kutcher and Mila Kunis. However, the letters were disjointed, tone deaf, and offered generic platitudes. The strategy backfired - bigtime. Ashton and Mila had to defend their letters publicly and Danny was sentenced to 30 years in prison. Danny relied on his friends and family to write the letters and his lawyers to manage the process. It turned out to be a big mistake that cost him dearly. Character-reference letters should fortify the plea for mercy, not undermine it.


Character-reference letters are a powerful tool that should be wielded carefully before your sentencing. When crafted thoughtfully and strategically, they can provide judges with valuable insights that influence the outcome of a case. By focusing on authenticity, storytelling, and aligning with the values of law-abiding citizens, you can improve your prospects for a more favorable sentence. According to the United States Sentencing Commission, for individuals that received a downward variance, the average sentence reduction was 26.2%! On a five year sentence, that is a 1.5 year reduction!

How much are you willing to invest for the chance to receive a lower sentence?


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