Over the course of the last 28 years, the Letters to Santa event has raised nearly $4 million for families in need.
As founder of Poverty Alleviation Charities, producer/director Heather Whinna spearheaded the event in Chicago. This year, Letters to Santa took place in Chicago in partnership with hospitality company Convene as a gala fundraising event at Willis Tower before expanding to Los Angeles for the first time as a 24 hour marathon event.
Joined by her husband, audio engineer Steve Albini, Whinna’s events utilize comedy and music to make a difference at the holidays.
“To my mind, the most important and unique thing about Letters to Santa, the entire project, is that it’s the most direct and most efficient charitable endeavor that I can even conceive of,” said Albini prior to the Chicago gala earlier this month. “Every dollar of it is donated immediately into the hands of a poor family. All of the overhead in the charity is taken care of by the benefactors of the charity. So, it’s the most direct and most efficient way to get money into the hands of poor families.”
While many larger charities oversee fundraising efforts, far less actually see through the distribution of funds raised at the local level.
Nearly three decades ago, Whinna and Albini first began picking up actual letters to Santa from their local post office, fulfilling the Christmas lists provided by Chicago families in need. Each Christmas day, Whinna, Albini and other volunteers distribute the gifts purchased to local families along with a grant, providing a unique form of oversight that sets the organization apart.
“What I like about Letters to Santa is that most charitable things are about getting someone involved in some type of a mechanism or a process that will eventually help them, right? Well, Letters to Santa is direct and immediate help,” Albini explained.
“It’s the most important part of what we do,” Whinna agreed. “100% of the donation goes directly to a family on Christmas day. I will get your money and I am going to give it to them,” she said, highlighting the charity’s hands-on approach. “The thing that makes what we do special is that everything is organic, right? People from my high school just walked up as well as all of the performers,” said Whinna. “I’ve just been very lucky in my life that I’ve built a lot of circles of talented people around me who are always willing to do whatever I ask them to – which is a remarkable gift.”
Known for roles in films like The Goonies, Parenthood and Frozen II, actress Martha Plimpton spent time in Chicago in the 2000s working with Steppenwolf Theatre Company.
In Chicago for the Convene-sponsored gala event, Plimpton was clear on the important role Letters to Santa plays at the holidays.
“It’s incredibly important. Heather Whinna, who is one of my longest and dearest friends, is a person that I would fly to the ends of the earth for if she asked me. I just love this event,” said Plimpton. “I love the idea of it. And I love how it came about. I love that she spent the last 28 Christmases literally making people’s lives better by bringing happiness and joy to struggling families all over this city. I don’t know what the city of Chicago would be without Heather Whinna.”
Plimpton was joined on stage in Chicago by Windy City-born comedian John Mulaney, a Letters to Santa special guest who raised $25,000 for the charity by auctioning off a pair of photos with fans, later tweaking a batch of new material as he performed in front of the hometown crowd.
Earlier, Albini interviewed Irish singer songwriter Glen Hansard via Zoom, with the musician offering up a unique solo acoustic take on “Falling Slowly,” a 2007 hit for The Swell Season (Hansard’s folk duo with Markéta Irglová), from the soundtrack to the 2007 musical Once. “My friend, that was beautiful in ways that you can never imagine,” said Albini to Hansard as the segment wrapped, clearly moved as fans in attendance at the gala took over the lead vocal as the video call occasionally hiccuped.
In addition to performances by comedians Todd Barry and Dave Helem, and event hosts Nnamdi Ngwe and Patrick Rowland, actor, comedian and Saturday Night Live alum Chris Kattan delivered a set of holiday-themed jokes in full costume as an elf.
“It’s a great cause. And to be asked is a real honor,” said Kattan prior to the event. “I think it’s very important to give back and give as much as we can.”
Writer, actress and comedian Katie Rich was an on stage highlight during the Chicago Letters to Santa gala event.
Few Letters participants were as engaging as Rich. A writer on SNL for six years, Rich too was born in the Chicagoland area. On stage at the gala event, for each donation made, she delivered jokes written for SNL’s “Weekend Update” sketch that never made the air, nearly stealing the show as she cracked wise.
“I’ve been doing Letters to Santa for almost 20 years,” said Rich before taking the stage. “I’ve gone on Christmas day to visit families and it’s wonderful. It’s truly magical,” she said. “Sometimes, I think when you donate [to a charity], you don’t necessarily get to see what your generosity has done. But with Letters to Santa, boy do you get to see it. It’s just so palpable,” Rich explained. “I know this sounds cheesy but you truly learn what Christmas is about. You see these families who wouldn’t have had a Christmas otherwise. And it just makes you want to help more and more families, you know what I mean?” she said of the annual visits. “It’s exponential the way that it hits you. It’s unbelievable how you can see that this is a life-changing thing for them. And there’s no strings attached. ‘Here, this is for you. Have a good holiday.’”
