Secret Santas Share the Wealth, $100 at a Time

You don't have to be a billionaire -- nor a jolly, white-bearded figure out of folklore -- to make the holiday season remarkably sweeter for a stranger. Or a lot of strangers. Over the past few years, ordinary people across the country have been taking up the calling of Larry Stewart, the original Secret Santa.

For more than 25 years, Stewart marked the holidays by handing out cash anonymously to random people in need, $100 and sometimes even $1,000 at a time.

By the time he passed away in 2007, Stewart, whose life path had taken him from broke and hungry to millionaire, had given away in excess of $1.3 million, one individual at at time. And thanks to the publicity he got when he allowed his identity to be made public a few months before his death, his legacy continues. A cadre of people have taken up the mantle, anonymously performing random acts of kindness and giving, loosely organized as the Society of Secret Santas.

Going Where the Need Is

One such man told a bit of his tale to DailyFinance -- anonymously, of course; that's the Secret Santa way. Three years ago, he said, the recession motivated him to find a new way to give. He had read about Secret Santas in other parts of the country and decided to try it in Portland, Maine. That first year, he enlisted family and friends to help him give out $10,000 in $100 bills. He did the same in 2009. In 2010, he upped his giving to $20,000, and this week, he'll do it again.

Santa and his crew go where there are likely to be people for whom an extra $100 would be a real godsend. They pass out money to people in Goodwill stores and bus stations, among other places. "We can only stay about five to 10 minutes at one location because people will start calling others and we don't want a mob scene."

"It's an indescribable feeling, the appreciation in their eyes," he says. "It's not like writing a check to a charity."

The beauty of people receiving help this way, he continues, is that they are willing to accept it because it's from "Santa." "There is no stigma attached, they don't have to sign up for it or stand in line."

While he says his own economic situation puts him closer to the "1 Percent" than not, all the divisive talk is off point. "Everybody should focus on how they can help, not what percent they are in. Even if you can't give on a large scale, you can do something."

Secret Santa
Secret Santa

Giving Material Wealth, Gaining Spiritual Health

There's something about giving that is uniquely rewarding, says another Secret Santa, who personally knew Stewart. "Seeing the expressions of surprise, disbelief and joy on the faces of those you help, and in hearing their stories. It makes you appreciate what you have and gives you humility as you stand in the presence of their dignity."

He finds his beneficiaries at places like Salvation Army outlets, thrifts stores and laundromats in depressed areas. "I have given from $100 to a few thousand dollars, depending on the circumstances," he says. "That gift in turn can provide a night's shelter, a meal for a family, heat for a home, clothes for children. The list is endless."

Yes, he is wealthy, but in his view real wealth is not monetary. "It's rather spiritual, and for that we are all seeking our fortune. I pale in comparison to men like Warren Buffett and Bill Gates when it comes to giving and making a real difference in the lives of multitudes. People like them are my heroes."

Even the wealthy are feeling the pinch a bit this year, but neither of the two Secret Santas we spoke with said they'd entertained any thoughts of scaling down their giving. "Frankly, given our economy, now is the time to step up, not step back," says Santa No. 2.

Hearing him talk about what it means for him, it becomes obvious why he has no plans to dial back his giving.

"What we do makes even tough men cry," he says. "To personally reach out and give money or a helping hand to someone truly in need, without judgment and without conditions, will enhance your own life, bring you happiness and liberate your soul. I guarantee it. It's all about leadership, and the greatest gift I can give another is the inspiration to pass on random acts of kindness, and that by doing so, we can change the world."

Editor's Note: The Secret Santa in these pictures isn't one of the men mentioned in this article.