Larry Stewart, the Secret Santa who gave away $1.3 million
For 26 years, a Kansas City businessman handed $100 bills to strangers every December. He kept his name out of it until cancer gave him a reason to speak.
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Start with photos →In December 1979, Larry Stewart had just been fired for the second year in a row the week before Christmas. He was sitting in a drive-in restaurant in Kansas City, nursing the kind of mood that makes other people's good cheer hard to take. A carhop was working outside in the cold in a thin jacket.
He gave her $20 and told her to keep the change. She began to cry. "Sir, you have no idea what this means to me," he later recalled her saying.
The $200 that became a habit
Stewart went to the bank and took out $200. Then he drove around looking for people who could use a lift. He called it his Christmas present to himself. He did it again the next December, and the next. Over 26 years, the amounts grew from $5 and $10 bills to $100 bills, sometimes two or three at a time. He gave money in thrift stores, diners and parking lots.
By the time he was done, he had given away about $1.3 million. He started a website. Reporters sometimes travelled with him, but they had to agree not to name him or his company. He brought friends: Buck O'Neil, the Negro Leagues icon, handed out hugs while Stewart handed out cash. In 2006, Dick Butkus was set to join him in Chicago.
Why he revealed himself
In April 2006, doctors told Stewart he had cancer of the esophagus that had spread to his liver. He was 58. The chemotherapy was aggressive; he lost about 100 pounds. That November, weak from treatment, he decided to reveal his identity. He wanted to encourage other people to give, not to collect credit.
He told the Associated Press that the goal was bigger than the $100 bills: he wanted to speak to community groups about kindness and to inspire others to donate their time and money. "That's what we're here for," he said, "to help other people out."
Upload a photo + a few interests for each person → we draw names and hand every Santa gift picks they're more likely to love.
Start with photos →Why anonymity was the gift
Stewart's recipients did not have to apply, stand in line or prove they deserved help. The money arrived as a surprise from a stranger. That is a different transaction from a charity cheque or a company bonus. It preserved the recipient's dignity and made the giver's ego irrelevant.
He died in January 2007, at 58. His example inspired other anonymous Santas, including people he trained. The details are in the sources below; the lesson is simpler. The gift was never about the giver.
What it teaches a Secret Santa
- Don't make people perform. The recipient did not have to thank a committee or pose for a photo. A private link does the same thing: it lets someone receive without an audience.
- Keep the rules small and clear. A budget, a date and a wishlist are enough. The more conditions you add, the more the exchange becomes about the organizer.
- Protect the surprise. Anonymity is not a gimmick. It gives the giver room to be generous and the receiver room to be surprised.
You do not need $100 bills. You need a clear budget, a private draw and a way for each person to say what they like. The rules page covers the mechanics; the about page explains how this site keeps the organizer out of the pairings.
Sources
- Associated Press / The Spokesman-Review: Secret Santa no longer secret (19 Nov 2006)
- Los Angeles Times: Larry Stewart, 58; Secret Santa handed out $1.3 million (14 Jan 2007)
- The New York Times: Secret Santa, Facing Cancer, Encourages Generosity in Others (19 Nov 2006)
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Questions
Who was Larry Stewart?
A Kansas City businessman who gave away money anonymously as "Secret Santa" for 26 years. He revealed his identity in November 2006 and died in January 2007.
How much did he give away?
About $1.3 million, mostly in $5, $10 and later $100 bills handed to strangers in thrift stores, diners and parking lots.
Why did he stay anonymous?
He wanted the gift to be about the recipient, not about him. He revealed his name only when cancer gave him a chance to encourage others to give.
Upload a photo + a few interests for each person → we draw names and hand every Santa gift picks they're more likely to love.
Start with photos →Updated October 28, 2026