Farewell, and Thanks, to a Man Who Kept Kids Safe

By Equipo
17 Min Read

From the corner of West 25th Street in Manhattan, it takes 34 steps to cross 10th Avenue, more if it is a kindergartner dawdling, sippy cup in hand, to the private school on the other side. To get to Avenues The World School by crossing West 25th Street takes only 16 steps, even fewer if it is a frantic 12th grader bounding to be on time for first period.

Five days a week, in the bright early mornings of September and the creeping twilight of February afternoons, Richard Henderson, crossing guard, oversaw those arrivals, holding hands, bumping fists, hollering at traffic, picking up dropped homework.

“My man, Wilder,” he would call out to a 4-year-old boy.

“Spider-Man,” he’d chuckle at the preschooler clutching for dear life a figurine of his favorite superhero.

“Miss Seattle,” he’d address a third-grade girl, a new student from the West Coast who loyally wore a Seahawks cap every day.

Henderson, known as Richie, was a son of East New York, raised on public assistance by a single mother who died of cancer when Richie was just a teenager. He had no high school diploma nor even a general equivalency degree, but he had a good family and a job he loved as a crossing guard at a $65,850-a-year private school.

Every school day at the corner of 10th and 25th, children of great privilege were given over, for a fleeting few seconds, to the protection of a man of great warmth and responsibility. Henderson managed the flow of Ubers dropping off children and made sure the boys let the girls play football with them during recess.

Raina Gilchrist, a Spanish language instructor at the school, said Henderson connected with the students in a way that she, for one, could not, whether he was sharing secret handshakes with them or joining in their games at recess. He was comfortably direct, totally in charge, utterly reliable.

They adored one another, she said. “And boy, could he throw a football.”

In return for his work, companionship and perfect spirals, the parents and children at Avenues gave Henderson their respect and thanks — sometimes with a sizable holiday check, sometimes with just a cup of cocoa on a bitterly cold day.

Then, in January, a decade into his career at 25th and 10th, they would be there for Henderson when he was gone and it was his family that needed protecting.

Eyes and Ears for 1,900 Kids

School crossing guards form an unheralded army of men and women who, parish by parish, school district by school district, keep New York safe and hold it together. The city’s public schools require guards to speak English, pass a drug screening and do a week of training at the police academy. The agency that sent Avenues its contract crossing guards provides its own training.

But the talents most necessary in a crossing guard can be harder to measure: patience, imperviousness to weather, a sense of humor and, should the moment arise, a willingness to risk one’s life to save a child’s.

These foot soldiers of the city can be grandmothers in Woodside looking to fill up their days or graduate students in Fort Greene hustling to make the next tuition payment.

Or they can be steadfast guys like Richie Henderson.

The third and youngest son born to Lavina Joyce Henderson, Richie lost his father to AIDS and his mother to cancer when she was just 44. The older boys, Earl and Jermaine, tried to look out for him, and in Brooklyn’s 75th Precinct in the late 1980s, that took some doing.

The East New York neighborhood averaged 100 or so murders a year, and the local cops became infamous for their role in the precinct’s drug dealing and violence. Jermaine, the second boy, was shot five times in a hail of gunfire — once in the head, once each in his shoulder and back, once in each of his arms. It was a neighborhood beef, and there would be no arrest.

“The bullet in my head is still there,” Jermaine said.

Jermaine’s survival was no small miracle, and his mission afterward was clear, he said.

“Protect my little brother at all costs,” he said.

It turned out, Richie didn’t need all that much protection. He would become known as a gifted neighborhood mediator. He calmed disputes; he encouraged laughter; he brokered deals to just let stuff go.

“All he wanted to have was peace around him,” Jermaine said.

Henderson’s first jobs, perhaps not surprisingly, were as a watchman. They weren’t glamorous.

“He was security at construction sites,” his wife, Jakeba Dockery, said with a laugh. “Guarding dirt.”

Henderson met Dockery when they were teenagers. She went on a blind date with a friend of his and he tagged along. He wound up with her number and her lifelong affection. They had three children, two girls and a boy: Richie Jr. works as an exterminator with the city’s public housing authority; Lavina, named for Richie’s mother, is working to gain her welder’s license; and Janaya is a freshman guard on the varsity basketball team at East New York Family Academy, already drawing interest from college recruiters. Henderson became a grandfather to two little girls.

He arrived at 25th and 10th on Manhattan’s West Side as a contract worker in 2014. He was given a neon vest and charged with safekeeping many of the 1,900 children who turned up every day. It was a school with lofty aims.

“We will graduate students at ease beyond their borders,” its mission statement pledges, proclaiming that they will become “architects of lives that transcend the ordinary.”

Henderson was an architect of lives, too. The youngest children arrived calling his name; those who graduated came back to see him. Kids injured at recess were scooped up in his giant hands. He got Spider-Man a Hot Wheels set as a gift, and he cried with relief when he realized a student he thought had left the school turned out to have been studying overseas.

“I kept waiting,” he told the boy.

Elizabeth Litman, dean of students for the middle grades, told of how Henderson was especially vigilant at dismissal.

“A lot of kids would step out to 25th and 10th Avenue and not be aware of cars, and just be really excited to get pizza, to see friends and get into their after-school activities,” Litman said. “He was their eyes when they couldn’t really see or they weren’t really focused on the dangers that could be potentially around them.”

Back at the home they’d bought in the Crown Heights neighborhood of Brooklyn, Henderson would tell Dockery he’d seen some of the parents on television, stars of one kind or another. He was grateful for what Dockery called “decent money” — $2,200 every two weeks.

In the summer of 2023, the school honored Henderson’s contribution by making him a staff employee, something they had never done for a crossing guard before. He’d no longer work as a subcontractor. He would have a benefits package, including health care, a retirement plan and a life insurance policy.

“They gave him his roses,” Dockery said of Henderson’s status as a staff member.

She said her husband, imposing at more than 6 feet tall and more than 200 pounds, could be stern and demanding of his own children, but never with the kids at Avenues.

“Those kids, that school, they got the best of Richie,” she said with pride and not regret.

A Dispute, a Death, Despair

On Jan. 14, a Sunday, Henderson went back to the old neighborhood in East New York to watch an N.F.L. playoff game with friends. The next day would be a day off, Martin Luther King’s Birthday, so the load of laundry that needed to be done could be pushed off till then. He promised Dockery he’d be back in plenty of time to make his famous mashed potatoes for dinner.

“You got a big belly,” she used to tease him. “Nothing’s going to hurt that belly.”

Henderson and one of his friends, Anthony Williams, were headed home on the No. 3 train when there was a dispute inside the car they were riding in. Dockery said she was told a man and his wife and child were playing loud music, and another rider objected. When a fight started, Henderson intervened.

The police can’t confirm that. There were no cameras in the car, and witness testimony has been hard to corroborate. They have no reason to believe Henderson did anything but try to help, but the details of what took place may never be known.

Here is what’s certain: Richie Henderson was shot dead, gone at 45. Early news reports said Henderson was shot multiple times. Dockery said the death certificate she received said her husband was shot in the stomach, severing an artery in the big belly she thought would keep him safe.

That night, detectives took Dockery to Kings County Hospital Center. Henderson was already in the morgue.

“I didn’t get to touch my husband when he was warm, you know,” she said.

Dockery’s heartbreak has turned to considerable anger. She said the subway train sped through multiple stops after Henderson was shot, ruining any chance he might be saved. Photos of her dead husband later surfaced online, and she has taken steps to sue the Metropolitan Transportation Authority, alleging the pictures were taken and leaked by M.T.A. employees.

No one has been arrested in Henderson’s death. For Dockery, there is just a consuming absence — of comprehension and acceptance. The killer, she said, took her heart, took her life as she’d known it. And the killer took the $2,200 every two weeks that had kept their family afloat.

“We have a mortgage, we have bills,” she said. “We have children, and grandchildren. My husband was a great provider. My husband didn’t miss a day of work. I used to beg him to stay home with me. ‘No, I got to go get my babies, my students,’ he’d say. ‘They’re going to miss me. I got to be in the street with my babies.’”

Helping Hands

Beatrice Prince, a senior at Avenues, had known Henderson since she was in second grade. Henderson made sure she got to play at recess alongside the boys. She learned of his death on the news, and was shattered.

Leo, her brother and a 15-year-old sophomore at the school, wanted to soften the blow. He had never created a GoFundMe site before, but he set one up and asked Beatrice to spread the word. When he learned there were parents trying a similar effort, he joined forces with them.

“I knew I had to do something to give back,” he said. “The hope was it would blow up.”

The site quickly attracted a couple of thousand dollars. The next day during class, Leo sneaked a look, and a family had donated $10,000. Lots more had donated less. Each time he refreshed the page, he caught his breath.

The site wound up raising $378,000 from 1,704 donations.

“How crazy,” he said.

So crazy it knocked Jakeba Dockery sideways.

“Overwhelming,” she said.

Students, parents and teachers wrote cards and testimonials to Henderson. Becca Howlett, the director of people and culture at the school, delivered them to Dockery and read some aloud at Henderson’s funeral in Brooklyn. Howlett also cleared the way for Dockery to get some professional financial planning advice on how to handle the hundreds of thousands of dollars born of tragedy.

Dockery gave Howlett a necklace in thanks. The locket on it held some of the ashes of her husband.

Mya Cahana was among the students who produced a tribute to Henderson for the school’s monthly magazine.

She heard about Henderson’s unique bond with students in Gilchrist’s Spanish classes. She heard from Spider-Man’s parents, and about Henderson’s man Wilder. She herself had known Henderson for a decade.

“Richie was Richie,” she said. “He knew my name. He was someone looking out for me.”

The magazine carried a picture of the impromptu memorials to Henderson on the sidewalk outside the school — flowers, and a cup of cooling cocoa, too. Students also used chalk to write out Henderson’s name. One of those children, an eighth-grade girl named Cidney Homschek, worried about how long the sidewalk mural would last, and so wrote a poem that might last forever.

You’ll never get to notice how chalk cripples in my palm,

Fills a street with pigment,

Only to fade as rain washes by or

Footsteps stomp out their color

Now Mya will get to report that the local community board is seeking to have the stretch of 10th Avenue that Henderson patrolled named in his honor, on street signs that can’t be washed away.

Mya, the daughter of a doctor and a health care consultant, appreciates the yawning gap between Henderson’s upbringing and that of many of the school’s children.

But none of their differences, she said, were evident to her when she first encountered Henderson as a 7-year-old, an only child transplanted to New York from across the country, uncertain and a little afraid, wearing a Seahawks cap.

“Miss Seattle,” he called her.

Audio produced by Sarah Diamond.

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