At three o'clock in the morning on December 13, 2015, Richard Whitaker shot a man walking toward him and his girlfriend on a Seattle sidewalk. The bullet lodged itself in the right side of the man's chest, and by the time medics delivered the man to Harborview Medical Center, he was declared dead.

Whitaker did not know the man he shot. Fifty-five years old, short and stocky, Whitaker dealt crack, as he had done for most of his life. He started carrying a gun after he had been stabbed, attacked multiple times, and held up at gunpoint on the street, according to his publicly appointed defense attorney. Whitaker's first conviction for dealing crack came before he was old enough to drink, and three more drug convictions followed. Then assault, theft, attempting to elude. A burglary conviction lengthened his rap sheet, too. In 2014, Whitaker was convicted of yet another drug charge, but he failed to show up when the verdict was delivered. The judge in that case issued a warrant for Whitaker's arrest the same day, but he was never caught. Had Whitaker showed up for the verdict, or had authorities found him afterward, he would have been in prison—not on the Belltown sidewalk that night with the man he killed.

Brent McDonald had little in common with his killer other than the color of his skin and his gender. He was 49 years old, a working artist who taught woodworking to teenagers at the Coyote Central after-school program in the Central District. He was a handsome and fit African American man, with big, expressive eyes and a sprinkling of salt and pepper in his mustache and on his chin. People who knew McDonald described him as quiet, gentle, and endlessly supportive of his students' self-directed creativity. Once he helped a student, a 12-year-old girl, craft a solar-powered lantern in the shape of an eight-foot-long polar bear. That kind of ambition in working with students was typical. In the summers, McDonald helped kids create works of public art all over the city. In winter, he'd direct woodworking and metal projects indoors. The week before he was shot, McDonald was on track to finish helping a group of refugee middle-school students build soapbox derby cars.

Sometimes, after a day of working with students, McDonald would take the number 3 bus from Coyote Central to Belltown, where he used to live, and then head to Shorty's, a Coney Island–themed dive bar illuminated by a collection of pinball machines in the back. McDonald would drink there, catch up with old friends in the neighborhood, and play video games.

On that early December morning, one year ago, McDonald was leaving Shorty's and Whitaker was hanging around on the sidewalk while his girlfriend stood next to him. Whitaker saw McDonald. Surveillance video reveals no altercation between the two men. It shows no aggressive behavior from McDonald, just McDonald walking by and the possibility that brief words were spoken. Soon after, Whitaker killed McDonald. Later, Whitaker's defense attorney would tell a judge that the shooting was done in self-defense, that it was motivated by Whitaker's streetwise vigilance and a particular concern Whitaker held for the safety of his girlfriend, Wendy White. Prosecutors would argue the opposite: that the self-defense claim was bogus and that Whitaker, who, like his victim, was African American, wasn't afraid of McDonald but simply annoyed by his presence. In October, a jury convicted Whitaker of murder. A month later, a King County Superior Court judge called a downtown Seattle courtroom to order to decide what justice for Brent McDonald would mean.

Richard Whitaker was born Richard Roundtree Jr. and, according to court testimony, grew up amid hard circumstances in South Central Los Angeles. He told a social worker hired by his defense team that his cousin was a founding member of the Crips, and that his father, his namesake, robbed a bank. After shooting at police during that bank robbery, Richard Roundtree Sr. left the family for prison. Whitaker was 6 years old at the time. Not long after, Whitaker became involved in gang life. "Gang membership was not optional in the neighborhoods in which Mr. Whitaker grew up," Whitaker's defense attorney wrote in a pre-sentencing brief. Whitaker was one of six children, and his mother, now raising them all by herself, worked two jobs. It wasn't enough. As a teenager, Whitaker dropped out of school to run with the gang members in his neighborhood and help support the family.

The same year that Richard Whitaker's father went to prison, Brent McDonald was born in St. Joseph, Missouri, to Charlesetta and Roscoe "Rock" McDonald. His family later moved to Seattle where, as a teenager, McDonald was swept up in the city's integrated busing effort. Both McDonald and his older brother, Brian, were bused to West Seattle High School. "The school was rampant with racism," Brian McDonald wrote in a letter to Whitaker's sentencing judge. "And I'm not talking about students—I'm talking about faculty. My first day at school, I had a teacher say to me that although she had not seen me do anything wrong, she was sure that I had."

Still, childhood friends described Brent McDonald as a creative kid bursting with productive energy, someone who loved dancing and roller-skating and sneaking out to B-boy competitions. McDonald's partner of 10 years, Danielle Logan, said that love of movement stayed with McDonald his entire life. As an adult, he practiced martial arts, but that was not his only outlet. Once, Logan found him roller-skating to disco music in their garage.

McDonald also possessed a rare ability to be present with others and listen, Logan said. "I feel like one of his superpowers was that he could really see you, and help you to see yourself," she told the judge at Whitaker's sentencing hearing on November 16. "And [he would] encourage you to help express that person in whatever creative way you were meant to do that."

One of the people McDonald encouraged was Logan's daughter, Alleya. "He helped raise my daughter, our daughter, for 10 years," Logan said, her voice breaking. "He was the perfect person to help with that job. She's more like him than she is like me."

During the decades that McDonald spent making art or mentoring those around him, Whitaker kept getting into trouble. Whitaker didn't see his father for 20 years after he went to prison, and when he finally did see his father again, it was through a prison fence on Puget Sound's McNeil Island. This was in 1989, before McNeil Island became a facility for dangerous sex offenders. Back then it housed a general population of convicted criminals, and Whitaker told his defense attorney that as he was being booked into McNeil Island to serve a two-year sentence for second-degree assault, he saw his father being released after serving a four-year sentence for escaping jail and several drug charges.

According to a social worker who interviewed him ahead of sentencing, Whitaker had in recent years tried to exit his drug-dealing career. After being released from prison in 2013 for another drug conviction, this one from 2008, Whitaker enrolled in South Seattle Community College for job certification training. He later told this social worker that he applied for several jobs but was never hired because of his criminal record, so he gave up and went back to selling drugs. This social worker also described Whitaker as hypervigilant, someone who constantly feared people were after him. "Clinically, he would benefit from a mental health evaluation with an eye toward post-traumatic stress disorder," she wrote in a psycho-social evaluation submitted to the sentencing judge.

On November 16, 2016, a little more than 11 months after Brent McDonald died on the pavement of a Belltown sidewalk, two King County Jail officers led his killer into a courtroom crowded with McDonald's friends and family. Richard Whitaker wore a red jumpsuit and orange socks with sandals. The officers removed his handcuffs as he stood next to his attorney, facing the sentencing judge.

Danielle Logan stood just feet away from her partner's killer and told the judge about the man she loved. She held up pictures of funny faces he used to make and described the outdoor rooms he built so the family could spend their entire summers outside. When Logan was finished, Roxanne McDonald, Brent McDonald's sister, approached the bench.

"We love him so much," she said, her voice cracking into short, uneven sobs.

Roxanne described her brother's goofy laugh, how kind and helpful and caring he was. "And just the important work he did with the kids at Coyote Central," she said. "You see evidence of that all over the city."

The impact of McDonald's life now well beyond question, the proceedings turned toward a more difficult question: What constitutes justice? What could possibly constitute justice in the eyes of McDonald's surviving family? What could possibly constitute justice in the eyes of Whitaker's family? Or in the eyes of Whitaker himself?

In court, Logan didn't answer these questions directly. McDonald's sister, Roxanne, did.

"It's hard to take, that someone who brought so much kindness and beauty and joy into the world was taken in such an ugly and violent and senseless way," Roxanne told the judge. "I want to ask the court, please give Richard Whitaker the maximum sentence allowed for causing the death of my brother, Brent McDonald."

For murder in the second degree and unlawful possession of a firearm in the first degree, the state prosecutors asked for the maximum: 457 months, or 38 years, in prison. For Whitaker, now 56, with a bullet still lodged in his hip from a prior shooting, 38 years in prison would likely mean dying behind bars. In court, Whitaker's defense attorney—after bringing in the context of Whitaker's life, after describing the absence of choices he had after being incarcerated—asked for 15 years instead.

Once Whitaker's defense attorney had made his case, he invited two women to approach the judge to speak. They had been sitting together quietly in the middle of a courtroom bench that was otherwise populated by Brent McDonald's friends and family.

One woman, significantly younger than the other, helped up her elderly seatmate, who was wearing a full-length winter coat and hat. Together, they moved close to the judge's bench.

"I love my brother very much," Deborah Roundtree, the older woman in winter clothing, said. Richard Whitaker was her only surviving relative and had been helping her family for years, she explained. Yes, he sold crack. Yes, he had been incarcerated. But when her family was swamped in eviction notices and electricity bills, it was Whitaker, the brother standing to the left of her in the red jumpsuit, who would step in and make the difference between having lights and food or going without. "He's all that I have left," Roundtree continued. "I don't want my brother to die in prison, and I don't want him to die, or have anything happen to me or mine when my baby brother's in prison."

She continued, her words faltering: "I know that he can't take it back, but please, your honor, I'm just asking for some type of leniency for us. And I'm sorry for his family, too. With all my heart, I'm sorry. I've faced so much death in my life—I know what that's like. We've lost 11 people in our family in four years."

To illness or violence, Roundtree didn't say.

After Roundtree finished, the younger woman, her daughter Pasjonette, spoke. "My uncle in my life has always acted as a protector," she said. She, too, asked the judge for leniency.

Then Whitaker turned his back to the judge, faced the McDonald family, and placed his hand over his heart. It was the first time in court that he had addressed his victim's family or displayed much emotion at all. "I'm very, very, very, sorry," he said, his eyes wet. "And I would just hope, if you take it from your heart, to forgive me."

Sentencing hearings like this one happen multiple times a day, every day of the week, in courtrooms across the country. Each one, including this one, becomes a test of what we call justice.

"I have been thinking about justice," Brian McDonald, Brent's older brother, wrote in his letter to the sentencing judge. "And I realize I have no idea what the word means. We so often use it to mean vengeance, but I haven't the stomach for vengeance. I discovered after my brother was killed that hatred does not come easily to me."

McDonald's letter, a searching meditation on cause, effect, and recompense, continued: "I have no idea of the forces that shaped Mr. [Whitaker]. He is slightly older than I am, which means he undoubtedly suffered many of the same indignities that Brent and I did. Those who don't have to suffer the constant insults and slights and plain injustices that occur because one walks around in black skin have a hard time comprehending what it does to one's psyche. Sometimes the path of least resistance is to live down to the expectations others have of you. The struggle to prove your worth or humanity can sometimes be a heavy load and sometimes people break under the strain."

He wondered, in his letter, if his brother's killer might have grown up in a house with lead paint, "as so many poor children of color have." He wondered if his brother's killer might have grown up "in a house without love." He wondered why we, as a society, don't stop perpetrating injustices "against little kids." He wrote: "Because we don't bother to do that, my brother is dead and Mr. [Whitaker] will more than likely spend the rest of his life in jail. For me, this is two lives wasted. I guess I'm saying I wish we had a different system. But this is the system we have."

Brent McDonald had little in common with his killer, Richard Whitaker, other than his gender and the color of his skin. But on that sentencing day in court, the jury's verdict having been delivered five weeks earlier and the punishment now in the judge's hands, Deborah Roundtree pointed something out. It was a simple observation. It was a heart-wrenching truth. Both Brent McDonald's family and the family of Richard Whitaker do have one thing binding them together: a connection to a black man they loved, believed in, and relied on.

The face of Judge Hollis Hill, a white woman with 42 years of experience in the criminal justice system, offered little indication of what she may have been feeling that day. Her sober, focused expression didn't change between hearing McDonald's family mourn for their loss and hearing Whitaker's family plead for leniency.

Judge Hill told the courtroom that she hoped the sentence she imposed would bring some measure of comfort to Brent McDonald's family, to help them in their process of grieving and healing.

"To Mr. McDonald's brother, who wrote to the court that he did not know what justice is, all I can say is I understand why," she added. "Justice cannot bring home your brother, and the friend, son, partner, mentor, colleague, and creative spirit that Brent McDonald was to so many. And neither can justice repair the broken man who stands before me ready to be sentenced."

Judge Hill said that Whitaker's family history also resonated with her. Speaking directly to Whitaker, she said: "I would have preferred to be on the front end of your life when you were a child with unaddressed needs than at this stage of your life, required to impose a just sentence. But, ironically, Brent McDonald was a man on the front end of the lives of many children and youth, kids of color, kids who needed a role model, kids who needed a mentor. Because of your efforts, those children are victims, too."

Hill then sentenced Whitaker to 34 years, just four years shy of the punishment the state prosecutors and McDonald's sister wanted, but effectively life in prison. Soon, McDonald's friends and family would be hugging one another in the hallway outside the courtroom with relief, with the knowledge that the man who killed their loved one wouldn't be able to do to others what he had done to them.

Brent McDonald's family couldn't see Richard Whitaker's face as Judge Hill read the sentence, but they could see that he fumbled so badly with the pen given him to sign his sentencing paperwork that he dropped it to the floor. Whitaker's defense attorney then picked it up, handed it back, and allowed him to finish.

Deborah Roundtree sat still, staring straight ahead, as Judge Hill spoke. As Whitaker was put in handcuffs again and led away, she looked up at her brother and said something just loud enough for him to hear: "I love you, baby."