Why Most Character Letters Are Useless—And How Mine Helped Me Get 28 Months Instead of 60

Before sentencing, people kept telling me, “Get as many character letters as possible.” So, I almost made the mistake that most defendants make—sending the judge a stack of generic letters that meant nothing.

Judge Mark Bennett made one thing clear in his interview:

"I value a letter from a janitor who knows you over a senator who doesn’t."

That was a wake-up call. It’s not about how many letters you get. It’s about who writes them and what they say.

Most Character Letters Are a Waste of Paper

Judges have seen it all. They know when a letter is real and when it’s just someone doing a favor. I wanted my judge to read letters that actually meant something—letters that showed who I was beyond my crime.

Here’s what I learned:

🚫 Bad character letters:

• “Jason is a great guy.” (No proof.)
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• “Please be lenient.” (Judges ignore this.)
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• “I can’t believe Jason is in this situation.” (Comes across as denial.)

✅ Strong character letters:

• Told real stories about me—who I was before my crime, not just after.
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• Came from people who knew me personally for years, not just acquaintances.
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• Acknowledged what I did wrong but explained why I was more than my worst decision.

The Letters That Mattered Most in My Case

The most powerful letters came from:

1️⃣ A former colleague – He wrote about my work ethic and how I was the guy people relied on when things got tough. It showed I had real value.

2️⃣ A community member I had helped – Someone I volunteered with before sentencing shared how I had stepped up when others wouldn’t. That mattered.

3️⃣ My family—without begging – They wrote about what I had learned and how I was working to rebuild trust, not just how much they loved me.

Judge Bennett mentioned that letters should never tell a judge what sentence to give. That’s a huge mistake. Judges hate when people try to do their job for them.

How It Helped Me Get 28 Instead of 60 Months

My judge didn’t skim through my letters. He referenced them in court. He saw that I wasn’t just someone trying to get out of trouble—I was someone who had built real relationships and had people who still believed in me.

Without those letters, the prosecutor’s version of me might have been the only thing my judge had to work with. That’s why this matters.

If You’re Facing Sentencing, Don’t Waste This Opportunity

Most defendants do the bare minimum when it comes to character letters. They ask a few friends to type something up, never read them, and just hand them over.

That’s a mistake.

If you want your judge to see you as more than a case number, character letters need to be done right. I put serious effort into mine—and they played a role in helping me get home sooner.

Will yours?