The Aptly Named SantaCon

I'm not 100% certain that Boston has SantaCons - a pub crawl where runners/drinkers wear Santa outfits and raise money for charity. But I'eve certainly seen the Santa-garbed pub crawlers doing their December buzzing around town.

I'd say it looks like fun, but to me it actually doesn't. Even if I were 50 years younger, this sort of event is way too extraverted to be my jam. I'm more the make-a-donation and/or show-up-and-actually-do-something to an actual charity kind of gal, without running around like a maniac, let alone shaking friends and family down for a donation. And this doesn't even take into consideration that the idea of pouring beer down my gullet and running to the next watering hole to that I can pee is beyond fathoming. Me? I just don't go pub-to-pub a-wassailing

But, hey, great that folks are thinking "charity" rather than just obsessing about Christmas shopping, wrapping, cookie-baking, and decorating.

Unfortunately, the NYC edition of SantaCon has been running something of a Grinch con.

On its website, the organization bills itself:

...as “a charitable, nonpolitical, nonsensical Santa Claus convention that happens once a year to fund art & spread absurdist joy.” (Source: NY Times)

Participants buy official badges - the price in 2025 was $17 - and the take goes to local charities like City Harvest, the City Parks Foundation and the Flatbush Development Corporation. But some of the proceeds have, grinchedly, made their way into the NYC event organizer's pockets. (In addition to the badge money, SantaCon NYC gets a cut of the action from the bars for whatever the crawlers consume along their merry and none-too-bright way.)

The lead organizer of SantaCon NYC, an annual Christmas-themed bar crawl that is both beloved and reviled, took more than half of the nearly $3 million the event raised for charity over five years, federal prosecutors said on Wednesday.

The organizer, Stefan Pildes, used his position as the president of the nonprofit that runs SantaCon to illegally divert the money into a separate company to finance “personal ventures,” and spent “hundreds of thousands of dollars” on “extensive renovations to a lakefront property in New Jersey, luxury vacations in Hawaii, Las Vegas, and Vail, extravagant meals and a luxury vehicle,” according to an indictment.

Santa, Baby, whatever happened to being nice rather than naughty? And that naughty could end up with Stefan Pildes ending up with 20 years in prison.

Not everyone loves SantaCon NYC.

The sight of people wearing red and green and slumped over in doorways is a not-uncommon sign that the holiday season is in full swing.

The comedian John Oliver once described SantaCon as “a terrifying combination of binge drinking, public urination and trauma to small children that decades of therapy will never manage to reverse.”

But plenty of others say the SantaCon brings joy to the world. There are the inevitable "meet cute" stories of couples who got together on the run. And then there's the charity angle. (There are allegations of some dubious financial activity on SantaCon NYC's part, including involvement with cryptocurrency and the Burning Man festival. Quite a combo!)

Pildes has set up a couple of other organizations adjacent to SantaCon NYC, and funds flowed among those orgs, funding Pildes personal professional/creative efforts and diverting pay for the property renovations, concert tickets, vacations, meals and luxury vehicle, prosecutors said.

Pildes is pleading not-guilty.

We'll see whether he'll be having himself a merry little Christmas. And whether he'll be having it up and over the river.

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Image Source: SantaConNYC