By Sara Kropf

When about 98% of federal criminal cases end with a plea bargain, the sentencing process plays a much larger role in a white-collar defense lawyers’ practice than most people realize. At sentencing, we try to focus the court on the client as a person and not as a “defendant,” and this involves trying to describe our clients’ good qualities and acts.

Some judges are more willing to consider this information than others. As Judge Jed Rakoff explained a few years ago:

If ever a man is to receive credit for the good that he has done, and his immediate misconduct assessed in the context of his overall life hitherto, it should be at the moment of his sentencing, when his very future hangs in the balance. United States v. Adelson, 441 F. Supp. 2d 506, 513-514 (S.D.N.Y. 2006).

At sentencing, the court is charged with imposing “a sentence sufficient, but not greater than necessary,” after accounting for the “nature and circumstances of the offense and the history and characteristics of the defendant.” 18 U.S.C. § 3553(a). The sentence must “comply” with the various purposes in Section 3553(a)(2). An appropriate sentence is intended

(A) to reflect the seriousness of the offense, to promote respect for the law, and to provide just punishment for the offense;

(B) to afford adequate deterrence to criminal conduct;

(C) to protect the public from further crimes of the defendant; and

(D) to provide the defendant with needed educational or vocational training, medical care, or other correctional treatment in the most effective manner.

A defense lawyer has a few arrows in her quiver to use at sentencing: a sentencing memo, her client’s own words at sentencing, and—the focus of this post—character letters. (If you need a primer on the federal sentencing procedure, here’s a good starting point.)

What Is a Character Letter?

Character letters are written by people who know your client: friends, family, neighbors, co-workers, religious or spiritual advisors, teachers, and coaches. They are fairly short, maybe a page or so. They describe how the writer knows your client and how long they have known him.

The letters need not address the offense conduct. The purpose is to describe what your client is like beyond what the court has learned in the indictment, plea agreement, or statement of facts.

They are usually typewritten and addressed to the judge. They can be sent directly to the court, but the better practice is for defense counsel to gather them and attach them as exhibits to your sentencing memo.

It’s fine if they aren’t eloquent or if they have grammar errors. They will reflect your client’s community, both past and present.

How and When Do You Get Character Letters?

Your client should help you get character letters. They should ask their friends, family, colleagues, and others directly for them. Your client should collect the letters and forward them to you. Consider giving your client a short template email to use to ask for a letter, so that people understand what they need to include in their letter, to whom to address the letter, the deadline for sending the letter.

Many of our clients have felt entirely powerless through the process, and this is a welcome chance to offer real help to the defense team.

Now, I have had a few clients who have tried to keep the entire process quiet. They simply do not want to reach out to a lot of people who may not have known about the criminal charges or their plea to ask for a character letter. I do my best to convince them that the embarrassment is minor compared to the potential benefit of the letters. Sometimes that works and sometimes it doesn’t.

It’s also worth reminding your client that he should ask for the letters but understand that not everyone will write one. The friend or family member may be angry or embarrassed themselves about the criminal charges.

Even though the sentencing hearing is generally scheduled far in advance, you should start working on obtaining character letters immediately. It always takes longer than your client thinks. Set a deadline long before when your sentencing memo is due—maybe two or three weeks before—and check in regularly with your client about what letters they have received. You’ll want to incorporate the character letters into the memo and look for themes across them. It’s inevitable that a few will trickle in near the end of the process but try to give yourself enough time to digest and synthesize them into your memo.

What Should Be in a Character Letter?

Here are a few things that a helpful character letter includes:

  1. The letter is addressed to the judge. “Dear Judge Smith.”
  2. The writer should explain how they know your client and how long she has known him.  “I am Mr. Jones’ next-door neighbor and I have known him for 25 years.”
  3. The writer should describe your client as a person in her own words and consider telling a story about him to bring that description alive and give it a concrete focus. Telling the judge that someone is “kind” is not as persuasive as giving specific examples of that kindness. “After my husband died, Mr. Jones would shovel my driveway and cleared my car during every winter storm. He has run errands for me, bought me groceries, and checks in on me regularly to make sure I’m doing ok.”
  4. If it is true, the writer can describe the effect of a long sentence on the writer or on your client’s family or community. “Mr. Jones is an important part of our neighborhood. I know that his family and our whole community will suffer while he is in prison. I see him playing with his young children every day and working hard to support them.”
  5. The writer can acknowledge the offense but shouldn’t try to explain it or defend your client. “I know that Mr. Jones was convicted of fraud, but I’m writing because I want you to know who he is as a person.”
  6. The writer can thank the judge and request a lenient sentence. “I am asking you to impose a lenient sentence on Mr. Jones and take into account his entire life rather than just what he was convicted of here.”
  7. The writer should include her full name and contact information.

Do Character Letters Matter?

It’s hard to know. Judges do routinely refer to them in their sentencing pronouncements. Sometimes judges turn them around on defendants, though. They will point out all the wonderful character letters they read and how much love and support your client had. The judge will then profess confusion about why your client would throw all that away to commit the crime here.

There’s no guarantee that these letters will help. But I’ve seen them do some good at sentencing and help the judge see my client as more than a case number and some arguably bad conduct.