Viacom Ad Sales’ Greg Cantwell Leads the Stocking Stuffing Assembly Line for Manhattan’s Homeless

by Stuart Winchester, Viacom

Eleven years ago, Greg Cantwell had an idea.

It was Christmastime. Complaints rained around him, about the commercialization of Christmas, about the excess of presents.

So he asked himself, would anyone really care if he spent half as much on presents and put the other half toward something a little more worthy?

“I couldn’t think of anyone in my life who would care, so I thought, why not just do it?”

But where to put the resources? That wasn’t so hard, as it turned out. He’d been in New York a long time. He knew how difficult conditions were for homeless people, especially around the holidays.

So he and two friends met at his apartment, and they assembled a couple dozen Christmas stockings. They stuffed them with a toothbrush, toothpaste, socks, cookies, gum, candy canes, a McDonald’s gift certificate, a five dollar bill.


Cantwell, right, stuffing an enormous pile of stockings at his Brooklyn apartment with fellow Operation Santa Claus volunteers Carlos Gonzalez and Viacom employee Judi Sadon. Photo courtesy of Operation Santa Claus

Then they threaded their way through Manhattan’s East Village and handed the parcels out to the homeless. They hit Tomkins Square Park and Washington Square Park and Avenue A and anyplace else where they could find someone who could use a little extra.

“We were astonished, the reaction we got from people,” Cantwell, a client planning director for Viacom Ad Sales, recalls. “They were just not expecting it.”

Operation Santa Claus was born.

Cantwell has repeated the effort each year since, generally on the weekend before Christmas. Planning starts a minimum of two months in advance, with a Go Fund Me page and an email blast and social media posts.

As donations accumulate, Cantwell and “Chief Elf” Luisa Alves, who works in Spike’s inventory team, coordinate to determine how many stockings they can afford and what will go in each. A mammoth trip to Costco follows. They fill four or five shopping carts. Cantwell orders the gift cards in bulk from McDonald’s.

On the designated day, Cantwell invites everyone out to his Williamsburg home for a sangria party. A mammoth assembly line snakes through his two-bedroom apartment. Dozens of volunteers drop up to 50 items in each stocking. In 2015, they assembled 250. The goal for 2016 is 300.

It’s a novel project, a flourish of goodwill and selflessness that pushes back against the relentless commercial tide of the holiday season. People have noticed. A few years ago, NBC local news in New York featured Cantwell and Operation Santa Claus in a segment:

Each year, the event grows larger. Each year, Cantwell rouses the volunteers with a speech just before they disperse across the city.

The folks who will receive these are not expecting this, he says. Don’t just hand the stocking to them. Say hello. Acknowledge them as a human being. Listen to what they are saying. Explain to them that this is a gift that they put together for folks in the neighborhood (never say homeless). Most important, perhaps, ask them if they want the stocking before handing it over.



Operation Santa Claus volunteer Matt Charron talks to a homeless man in Manhattan’s East Village after giving him an Operation Santa Claus stocking. Photo courtesy of Operation Santa Claus

“Every human being has dignity, even if you don’t have a home and you’re sleeping on the streets,” Cantwell says. “You still have dignity as a human being and deserve to be treated with respect.”

Then they spread out across Manhattan in a half dozen teams of three or four, each with a captain.

There are moments.

One, a few years ago. Union Square. An 18- or 19-year-old kid bundled up against the icy December night. Cantwell hands him the stocking.

The kid just looks at it. “Man, no one’s given me a present in like five years,” he says.

Another. Two years ago, the first thing Cantwell’s team encounters is a homeless man with a baby. He could barely speak English. They gave him two stockings and moved on through the neighborhood.

Then, the most memorable. 14th Street, in the aftermath of the 2008 financial crisis. A man in his late 30s holds a cardboard sign. “Lost my job,” his sign declares. “Lost our home. Don’t have anything. We’re on the streets.” Beside him are his shellshocked wife and two kids, bundled against the New York winds. They each get a stocking. The little girl, astonished, looked up to her mom.

“Mommy – presents!”

Cantwell froze that moment. It distilled the spirit of Operation Santa Claus. “Whatever that family was going through, I knew I didn’t have the power to fix their problems, but that little girl had something that night,” Cantwell said. “Everybody who’s ever been a kid knows that that’s her Peppermint Patty. That’s her gum. Her parents might take the money and the McDonald’s gift cards, but those other things are hers.”

These interactions can be starkly humanizing. Alves – Operation Santa’s “chief elf” – traditionally stakes out Manhattan’s sprawling Port Authority bus terminal, where a labyrinth of corridors and levels provides shelter for large numbers of homeless people escaping the brutal New York winter. With so many in such obvious need, the stockings, which are each stuffed with a hat, scarf, or pair of gloves, are typically welcomed eagerly. But not by one woman, who looked inside and handed the stocking right back to Alves.

She was shocked. The woman obviously needed warm clothes. “It turns out that she didn’t want the hat because she didn’t want to mess up her hair!” Alves said. “We were both cracking up because I told her that I don’t like to wear hats either for the same reason. I just felt like it was a real moment that reminded me we are all human, and us girls all have the same ‘problems.’”


Luisa Alves laughs with a homeless woman at Manhattan’s Port Authority bus station as they bond over their shared concern for hat hair. Photo courtesy of Luisa Alves

Over time, the stockings have evolved. They’ve asked shelters, “What do they need that they’re not going to buy?” So they now include Band-Aids, Q-tips and hand sanitizer alongside the granola bars and sugary snacks.

In 2006, the year after he launched Operation Santa Claus, Cantwell started working for Viacom as an account executive in Spike Ad Sales. He couldn’t believe the reaction from his coworkers. Each year, dozens donate money and 15 to 20 colleagues show up in Williamsburg to help assemble and distribute the stockings.

“I was really happy with the way that people who work at Viacom embraced this,” he recalls. “They would come by and bring money or supplies, or they wanted to help out. There’s a really generous spirit among the people who work here, and the way they act and the way they treat each other.”

The help is vital. The event does not have a website. They do keep a Facebook page, but they don’t spend money on anything other than supplies. And Cantwell has realized he doesn’t have to do everything himself. All of his supporters have social media pages. If they stump for Operation Santa Claus on their newsfeeds, the calls for donation can reach thousands of people instead of a few hundred.

It works. One volunteer’s neighbor – a person Cantwell has never met – donated $200 last year.


Alves and fellow Operation Santa Claus volunteer Sam Turner pose with some men at Port Authority after delivering them stockings. Photo courtesy of Luisa Alves

Cantwell has been wired for philanthropy since the late 1990s, when he and two friends set up a scholarship foundation to memorialize a college friend who had died at age 23. They awarded more than 150 scholarships before shutting the fund down in 2008, when everyone felt ready to move on.

Operation Santa Claus, which remains small and intimate, helps him carry on this charitable spirit. “I think that kindness matters, and I think that empathy matters, and this is a good reminder to everybody to be kind to try to do things for people,” he says. “When I tell people this, and when they come, and they walk up to another human being and you say, ‘Here,’ and then they smile and hug you, there’s something about that that’s very visceral and people relate to that. I’ve never had anybody do this who wasn’t happy they did it afterwards.”


Sam Turner (right) and another volunteer pose with a homeless woman at Manhattan’s Port Authority. “She was one of our favorite people we’ve ever met,” said volunteer Luisa Alves, who took the picture. “She was so happy and kind and in great spirits, so we chatted a while.” Photo courtesy of Luisa Alves

Now in its 20th year Viacommunity, our social responsibility umbrella, has become more than just something we do – it is part of who we are, a core value of our company. To underscore how deeply embedded giving back is to our identity, we are profiling 20 employees who embody the Viacommunity spirit in their everyday lives. 

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