In its toughest year, Christmas in the City shares gifts and joy with families facing homelessness

Alex Bradford prepares to load a vehicle with gifts.Pat Greenhouse/Globe Staff

Boston’s biggest annual children’s Christmas party clung to its most elemental goal Sunday, despite the pandemic: that local children facing homelessness receive a gift they had requested from Santa.

It is hard to imagine a more difficult year for the family that created and runs the event, and a more difficult environment in which to pull it off.

This year, the Boston Convention and Exhibition Center, where the event is usually held, houses a field hospital for COVID-19 patients. Jake Kennedy, who started the event with his wife, Sparky, died of ALS in October. A contractor building a small addition to accommodate Kennedy’s condition at their home in New Hampshire recently contracted the virus, and Sparky and a son have been forced to quarantine.

“Today has been the worst since Jake passed,” said Sparky Kennedy in a phone interview Sunday. “Christmas in the City is what we did together, and we loved it.”

But despite the challenges, 600 to 700 children in Boston area shelters will get the gift they asked Santa for in wish lists submitted to the Christmas in the City organization, according to Kennedy, who has run the event with her family for 30 years. Parents and caretakers will get bags of useful items.

“We’re … just continuing on with his memory,” she said Saturday, after reading the last of the condolence cards. “That’s what Jake would have wanted.”

Alex Bradford, right, and Megan Greeley prepare to load a vehicle with gifts that were held in their South Boston apartment. They are going to a representative of Nuestra Comunidad in Roxbury.Pat Greenhouse/Globe Staff

The day was different but still shared the bright spirit of the effort the couple started decades ago.

“There’s no winter wonderland,” she told the Globe earlier this week. “The kids don’t get the experience of what we’ve come to expect as Christmas in the City. But we are going to carry the spirit to as many kids as logistically possible.”

The Kennedys began the tradition as a young family in 1989, throwing a party for just shy of 200 mothers and children at Boston City Hall, according to the fully volunteer-operated organization.

The event, which began shortly after Jake’s father also died of ALS, grew steadily into the enormous occasion it has become in recent years, giving some 20,000 gifts to children living in shelters — and then another 10,000 the day after to other families who are struggling, Kennedy said.

Last year, the event involved 6,000 homeless children and their parents or caregivers, with performances by Blue Man Group, a gospel choir, and an Afro-Caribbean band, along with costume characters, a petting zoo, amusement rides, Santa Claus photo booths, face paint, manicures, haircuts, dental screenings, flu shots, snowflake confetti, and plenty to eat.

“It puts your brain into someplace really magical. It makes you believe it’s real,” Kennedy said Sunday. “That got us to believe in Santa and the magic of the holidays.”

The program has added other annual events over time, including a Thanksgiving food giveaway, a family transition assistance program, tuition assistance, a Halloween event, and a job fair, according to the organization. Most events had to be canceled this year.

Thanks to all that work, Mayor Martin J. Walsh of Boston praised Jake at last year’s Christmas in the City, calling him “my hero.”

“Many of you in this room might not know him personally, but he does this because he loves you,” Walsh said that year. “He loves every single family in our Commonwealth, in our country. . . . He is my hero.”

Jake, who was 64 then, had begun to struggle with speaking, a complication of ALS, a progressive neurodegenerative disease. But he told the Globe that day that the thousands of volunteers were a central component of what made the event special.

“When you ask people what they like best — the winter wonderland, Santa, the food, the Blue Man Group — they all reply, ‘This is the first time in our lives we’ve been treated with dignity and compassion,’ ” Kennedy said. “That’s because of the volunteers.”

This year, as the Kennedy family grappled with Jake’s condition and death, those volunteers stepped up to usher the event through the difficult time.

“It’s a well-oiled machine by now,” Kennedy said Saturday, the day she finally finished reading the stack of condolence cards that have come since Jake’s death. “These [volunteers] have been doing this for years, and they have their jobs.”

Cal Brokamp, 33, who runs food distribution for the event, said volunteers jumped into action in September, as the Kennedys cared for Jake night and day.

“I think there wasn’t a doubt in our minds that it had to happen — and had to happen without [the Kennedys] saying that it has to happen,” said Brokamp, who has been volunteering since she was in elementary school. “And we just did it.”

Over the past months, those longtime volunteers developed a plan to get gifts for every child in 34 shelters — mostly in Boston, Cambridge, Somerville, Melrose, Lynn, Brighton, and Tewksbury — along with a backpack or diaper bag crammed with essentials, according to Lisa Blumstein, volunteer coordinator.

“Shelter captains” managed the logistics for each shelter, getting wish lists from kids (even those who moved in just days before delivery), coordinating with the shelters, and assigning an untold number of volunteers with procuring the gifts, packing bags, and getting everything ready for delivery. Deliveries were split over two weekends and were completed Sunday, she said.

The goal to get a gift for every child is nonreligious, and many of the core volunteers are Jewish, said Kennedy, who noted that she grew up with a “Hanukkah bush” in Brookline.

Alex Bradford and Megan Greeley, not shown, hand off gifts to a representative of Nuestra Comunidad in Roxbury. Housing resource program manager Selena Rodriguez accepts the gifts in an exchange between the two vehicles.Pat Greenhouse/Globe Staff

Personalizing those gifts is just one of many logistical challenges that seemed surmountable because of Jake’s example, said Brokamp, who managed the plan to get more than 1,000 meals to each shelter from local restaurants owned by people of color.

“I’ve known Jake my whole life and he never said no. ‘No’ was not in Jake’s vocabulary,” she said, remembering how Kennedy even accommodated mothers who needed their bottles heated, leaving the convention center stage to warm them in the kitchen himself.

“It would have been so easy to say no for a hundred different reasons,” she said of this year’s event. “But that’s not Jake and that’s not what he would want — and we couldn’t say no.”

It has been a grim year for many families, said Selena Rodriguez, a program manager at Nuestra Comunidad in Roxbury, which received a delivery of gifts Sunday afternoon. But excitement grew when the organization’s wish lists got distributed, she said, as most thought Christmas in the City would be canceled.

“I know what this means to a lot of mothers and children,” said Rodriguez on Sunday afternoon. “Definitely this is a lot.”

The South Boston couple who delivered gifts for 20 children at the facility — and who met at a Christmas in the City event three years ago — said they did not feel the same rush of emotion as when they got to give gifts directly to children, rather than handing them over to Rodriguez to distribute.

Still, “knowing they get gifts and have local restaurants catering dinner, it’s just as joyful knowing that they’re being taken care of and will have some joy this holiday season,” said Alex Bradford, 30.

Megan Greeley, 27, who has been volunteering since she was a child, said apart from honoring Jake Kennedy, the reason for finding a way to participate this year was simple.

“We all need the magic of Christmas in the City more than ever.”