Friend being sentenced? Tips for writing better character letters than Asthon Kutcher and Mila Kunis

As the world knows, Ashton Kutcher and Mila Kunis seriously bungled their assignment to write persuasive character letters on behalf of friend Danny Masterson, in the hopes of persuading a judge to not throw the book at him.

Even if you’ve led a law-abiding life, you might have a friend or family member who gets into serious trouble and faces time in prison. That’s when you could be asked to write a letter on this loved one’s behalf, describing their good qualities in the hopes of persuading a judge to show mercy.

A-list celebrity couple Ashton Kutcher and Mila Kunis found themselves in just this situation. Their longtime friend and TV sitcom co-star Danny Masterson needed them to write letters for him after he was convicted in May of two counts of rape, for attacks that occurred in the early 2000s.

As the world knows, Kutcher and Kunis seriously bungled this letter-writing assignment. After Masterson was sentenced to 30 years to life for the attacks, Kutcher and Kunis’ letters, which are part of the public record, were disseminated by news organizations and picked apart.

People across social media pounced on Kutcher and Kunis for describing Masterson — a convicted rapist — as a “a role model” and a big brother figure with “excellent character.” People called them privileged celebrities whose “tone deaf” letters perpetuated “rape culture.” For Masterson’s accusers in particular, the letters were “hurtful” and “retraumatizing,” with one, Chrissie Carnell Bixler, telling Kutcher that he was “as sick” as his “mentor.” It’s not known how Los Angeles Superior Court Judge Charlaine Alameda received the letters, but one legal expert told this news organization that they were “counterproductive.”

This negative response raises many questions, among them: How could Kutcher and Kunis have written better letters – ones that also didn’t result in an intense public backlash. It turns out that the answers to this question could be useful to anyone who is called upon to write a letter of support for a friend or family member who runs afoul of the law. Moreover, this letter-writing advice from legal experts can apply to other situations, including when you might have to vouch for someone at work or in your personal life.

The purpose of these letters…

These letters are common in criminal cases and are presented to a sentencing judge to balance out the “horrible” things the judge has learned about the defendant when reading the indictment or hearing testimony, said Colleen McCormack-Maitland, the deputy director of legal services at the Legal Action Center (LAC).

People writing these letters should never use them to re-litigate the defendant’s guilt, even if they staunchly believe that the defendant has been treated unfairly by the system. The trial is over, the jury has rendered its verdict. “That’s not the forum for this,” said McCormack-Maitland, a former public defender whose New York-based organization works to restore job, housing and other opportunities for people who arrest or conviction records.

Do these letters even help?

Whether the letters will be welcome by a judge depends on a variety of factors, McCormack-Maitland and other legal experts say, including the nature and seriousness of the crime and the individual judge’s legal philosophy and views on sentencing and punishment. Before writing the letter, it’s often helpful to talk to the defendant’s attorney, who can offer insight on the judge’s philosophy and temperament.

Judges have several main considerations when sentencing defendants, according to Los Angeles entertainment attorney Tre Lovell. They want to provide justice to the victims and mete out appropriate punishment. While they may be open to giving a defendant a second chance, especially a first-time offender, they also have to be mindful about protecting society. “Judges are thinking: Am I going to end up (in the news) as somebody who let someone out, and then they did something horrible?” McCormack-Maitland said.

Judges are statutorily required to impose certain sentences for certain crimes, though they often can operate within a range of sentences, and that range can be “huge,” McCormack-Maitland said. In certain situations, character letters can help a judge see that a lesser sentence, including probation, would be enough to teach a defendant a lesson.

Lovell is skeptical that character letters help much when the crime is “egregious,” such as a rape or murder. “The victim’s statement will have a much greater impact,” Lovell said. He can envision cases when the letters could bolster the idea that the crime was wildly out of character, or explain how the defendant was under some extreme pressure. Mostly, Lovell sees the letters helping in nonviolent crimes or when the defendant is a juvenile, when judges impose sentences that prioritize rehabilitation over punishment.

Expressing remorse can help defendants 

When defendants take responsibility for their crime, they are in a better position to show a capacity for change, which indicates to judges that they are less likely to re-offend. “If by the time of sentencing, if they’re still denying it, they’re done,” Lovell said. “If you’re not accepting responsibility, judges think you have the possibility of doing it again.”

Masterson’s lack of remorse was an issue with Kutcher and Kunis’s letters

Masterson vehemently denied the charges at his retrial (the first ended in a hung jury) and insisted he had consensual sex with his accusers. His attorney, Shawn Holley, said his legal team will file an appeal.

Masterson’s position created challenges for the more than 50 people writing letters on his behalf, including Kutcher and Kunis. It’s possible that the couple believed in Masterson’s innocence, but it’s evident they didn’t want to say anything in their letters that undermined their friend’s position.

But the result is that their letters failed to acknowledge that Masterson was convicted of serious, violent felonies, Lovell and McCormack-Maitland said. Still, friends who believe in a defendant’s innocence can still write an effective letter. Again, they should not use the letter to retry the case. But they can express concern about the seriousness of the crimes, then pivot and graciously offer to tell the judge about the person they know, McCormack-Maitland said.

Kutcher and Kunis’ letters essentially brushed aside the life-altering pain suffered by the victims, the attorneys said. Instead, they devoted paragraphs to what a great person Masterson was, praising his “innate goodness” and “caring nature.” In the context of Masterson’s crimes, this praise made parts of Kutcher and Kunis come across as “out of touch.” McCormack-Maitland said.

She acknowledged that the letters were effective when Kutcher and Kunis wrote about the impact a long prison sentence would have on Masterson’s 9-year-old daughter, given that it’s  well-documented that children can suffer life-long trauma when a parent is incarcerated. But other than that, McCormack-Maitland said that the letters were “counter-productive.”

Kutcher and Kunis “trivialized” Masterson’s crimes

The most questionable parts of Kutcher and Kunis’s letters came when they praised Masterson’s “steadfast” commitment to “promoting a drug-free lifestyle.” McCormack-Maitland said the couple came off as villainizing drug users, when substance abuse no longer is necessarily seen as a “moral failing.” Meanwhile, they held up Masterson’s a “great guy” because he doesn’t use drugs.

“To put Masterson on a pedestal because he doesn’t use drugs, when he’s just been convicted of rape, seems pretty out of touch in my opinion,” McCormack-Maitland said. “It makes it seem that they don’t understand the issues, and it trivialized what he was accused of doing, which was serious.”

Other critics saw the couple’s emphasis on Masterson’s anti-drug lifestyle as an effort to undermine the victims’ testimony after prosecutors alleged that the actor of plying his victims with drugs before raping them.

Other ways to write better character letters than Kutcher and Kunis

To McCormack-Maitland, it appeared that Kutcher and Kunis mostly wrote about their memories of the person they knew 20 years ago — when they were all working together on “That 70s Show.” That’s also around the time that the attacks occurred, she noted

To Lovell, the letters lacked specificity and failed to offer “unique” details that illuminated the person Masterson is now, especially whether he’s learned anything or changed for the better since the crimes occurred. That’s why it’s useful when defendants take responsibility: Their friends, for example, can write about how the defendants used their time, awaiting trial and sentencing, to go into therapy. Or, they can bolster defendants’ accounts about how they’ve already begun to take steps to amend for the crimes and to continue to contribute to society.

It also helps when friends can explain how they will continue to support the defendant, while the defendant is serving time or when the defendant is released from prison.

“The judge wants to know that the defendant won’t continue to be a risk to society, and that if he gets out earlier, that he’ll have people who will support him, helping him find work or housing, and will give him incentives to not commit anymore crimes,” Lovell said.