Nikki Greenberg stands in front of the mountain of school supplies gathered to fill more than 200 backpacks for the children of employees at The Cypress of Hilton Head. TIM WOOD

It is that time again, the time our kids absolutely dread. How did summer go so fast? How is it possibly back-to-school time?

As much as the students are fighting that feeling, the school supply shopping is just as stressful for parents.

One group of senior angels has taken it upon themselves to make sure the folks who help care for them don’t have to be concerned about the cost or hassle of filling those classroom supply lists.

Nikki Greenberg is a 10-year resident at The Cypress of Hilton Head, a continuing retirement care community with a staff of more than 350 employees trained to handle all levels of senior care.

As much as the 85-year-old Greenberg loves her three children, she sees the staff at The Cypress as her family these days.

“The care, the attention they give to us, they are just amazing people,” Greenberg said. “So we want to make sure that we take care of them whenever we can.”

It’s a dynamic far different from the stereotypical view the public has of some assisted living facilities. Greenberg and her family had heard of the stories when they were looking for assisted living after 20-plus years of independent living on the island.

“I could see this place was different and special from the moment I stepped on the grounds,” she said.

Soon after settling in at The Cypress, Greenberg met fellow resident Mary B. McDowell, who was the organizer of the Cypress Employee Emergency Fund, a resident-endowed account that helps employees cover expenses of life emergencies.

“If somebody has to move, fly to a funeral, cover their first and last month of rent, it’s what this is here for and it’s something that Mary educated me on from the first day and I wanted to be involved,” Greenberg said.

When McDowell began facing her own health issues, Greenberg promised that when her friend needed to step down, she would take over as the resident liaison to the employees community betterment committee and lead the organizing of the fund.

One of the biggest activities spawned by the fund is the annual back-to-school backpack supply drive. The idea was to raise money from residents to cover everything in a student’s classroom supply list, backpack included.

The concept started small, with 25 to 50 filled backpacks raffled off to employees that bought $1 raffle tickets. McDowell stepped down from the liaison position five years ago (she passed away in 2019). Greenberg immediately stepped in to lead as promised and has continued to grow the program over the past four years.

The octogenarian is a reserved and somewhat unwilling interview subject, only for the fact that the residents don’t spearhead the program for attention. They do it to express their love for The Cypress staff.

“That’s the only reason I agreed to talk here,” she said. “Folks need to know how special these folks are and how The Cypress is a truly extraordinary place to work. They are always in need of more qualified staff. It’s a very demanding job, and we as residents know that. They give so much of themselves, often to the detriment of their own families.”

It’s why this is such a labor of love for Greenberg and a crew of 40 resident volunteers who help fundraise throughout the year, sell raffle tickets for this event and a Valentine’s Day employee giveaway, and help order the supplies and fill the backpacks before the kids head back to school.

“With COVID, the stresses that we all felt were even more acute, but the pressures on the staff here were immense with all the protocols and the added health concerns,” said Greenberg. “They went so far above and beyond to make life as normal as possible for all of us, and we know it.”

Greenberg said that employee excellence is, in her opinion, a large part of why The Cypress has not experienced one COVID-related death to date.

The residents have gone above and beyond in 2021 covering the expenses of supplies from pens and pencils to folders, protractors and earbuds. Greenberg expects a record 220 backpacks to each be filled with more than $40 worth of school supplies.

Greenberg was born in Albany, N.Y., raised in Providence, R.I., and lived in places like Syracuse and Connecticut while raising her family. But she counts Hilton Head Island as her adult hometown, and both she and her family feel blessed to have found The Cypress for this later chapter of her island life.

“She has thrived there, it’s such a vibrant community and she cares deeply for those who care for her,” said her oldest child, Debbi, herself an island transplant who is proud of her Mom’s efforts to give back. “She’s so passionate about giving and paying it forward, and this passion begins with the care the staff gives to her and her friends.”

When asked to name some of her favorite staff, Greenberg is hesitant to single folks out. But she is a big fan of Galen Miller, the IT specialist at The Cypress and a member of the employees committee.

“He gives so much inside the building, but then he is such a force in the community as well, Greenberg said of Miller, who is president of the Hilton Head MLK Jr. Celebration Planning Committee. “He’s a big teddy bear and so representative of the staff family here.”

A storage space in a conference room at one of The Cypress community centers is filled with boxes of both school supplies and an abundance of COVID-necessary masks and gloves for staff and residents. It’s made the task of gathering and organizing the school supplies more challenging than most. But for Greenberg, a small task in comparison to the Herculean work she witnessed staff put forth every day during a truly unprecedented time.

“They rose to the challenges like they always have here, and so we’re ready to do that too. We’re going to get our crew together and figure out a way to make this assembly line work. It’s been a challenge, but our crew is up to it,” Greenberg said. “To see the smiles on our staff family’s faces, that melts any hassle away. We are all ready to fill some backpacks.”

Tim Wood is a veteran journalist based in Bluffton. Contact him at