A red coat. Sunglasses. A car full of hundred-dollar bills. And one specific small kindness, in a Mississippi diner, that started it all in 1971.
December 1971. Houston, Mississippi. A 23-year-old broke kid from Bruce, Mississippi, named Larry Stewart walked into a small diner called the Dixie Diner, ordered a meal he could not pay for, and prepared to walk out without paying. The owner — a man named Ted Horn — noticed Larry's anxious face, walked up behind him, pretended to find a twenty-dollar bill on the floor, and said, very quietly: "I believe you dropped this, sir." December 1979. Eight years later. Kansas City, Missouri. Larry Stewart — now 31, fired the previous week for the second Christmas in a row — pulled up to a drive-in restaurant in his car and saw a young carhop shivering in a thin jacket in the cold. He gave her $20. He said: "Keep the change." For the next twenty-six Decembers, he drove around the streets of Kansas City — and occasionally other American cities — handing out a total of $1.3 million in $100 bills to complete strangers. Nobody knew his name. Then in April 2006, he was diagnosed with esophageal cancer. He had nine months to live. He decided to tell the world. This is his story.
December 1971: A 23-Year-Old Walks Into a Diner in Houston, Mississippi
To understand who Larry Stewart became, you have to start in a small town in north-central Mississippi that almost nobody outside of north-central Mississippi has heard of. Bruce, Mississippi, in 1948 — when Larry Dean Stewart was born on April 1 — had a population of approximately 1,800 people. It was, and remains, a working-class lumber town nestled in the foothills between the Mississippi Delta and the Appalachian foothills. The dominant employer was a sawmill. The dominant religion was Southern Baptist. The dominant family structure was, in the way of small Southern towns in the late 1940s, large and tightly woven.
Larry Stewart's family was poor. Not catastrophically poor, but the kind of small-town American poor where a child grows up watching his parents do mental arithmetic on grocery prices in the canned-vegetable aisle. His father worked at the sawmill. His mother kept the house. There were several younger siblings. There was, for most of Larry's childhood, no central heating. By the time Larry graduated from Bruce High School in 1966, he had two clear instincts about his future. He wanted to leave Mississippi. And he wanted, very specifically, to make enough money that nobody in his family would ever again have to do mental arithmetic on canned-vegetable prices.
A Plan That Did Not Work, in Houston, Mississippi
By December 1971, Larry was 23 years old. He had spent the previous five years trying — with the cheerful incompetence of a young Southerner with more ambition than experience — to break into various small businesses along the I-55 corridor between Mississippi and Memphis. He had failed at most of them. He was, in early December 1971, driving back home to Bruce from a failed sales pitch in Tupelo, with approximately three dollars and twenty cents in his wallet.
He stopped, around lunchtime on a cold gray December day, in the small town of Houston, Mississippi — a courthouse town of approximately 4,000 people about thirty miles east of Bruce. He pulled into the gravel lot of a small roadside diner called the Dixie Diner. It was the kind of place that served meatloaf and gravy and fried okra and bottomless coffee for under three dollars. He had not eaten in twenty-four hours.
The Plan to Walk Out Without Paying
Larry Stewart went inside. He sat at the counter. He ordered the daily plate special — meatloaf, mashed potatoes, green beans, biscuit, coffee, $2.85. He ate slowly. He thought, the whole time he was eating, about the small mathematical fact that he had three dollars and twenty cents in his pocket and that the bill, with tax, would come to somewhere around $3.05, leaving him approximately fifteen cents for gas, which would not get him the remaining twenty-eight miles home to Bruce.
He decided, somewhere around the second cup of coffee, that he was going to walk out without paying. It was the kind of decision a person makes when they are 23, broke, ashamed, and out of better options. He waited until the owner — a man named Ted Horn, who had been refilling coffee cups one by one along the counter — was at the cash register with another customer. He stood up. He picked up his coat. He started walking, slowly, toward the door.
" I believe you dropped this, sir. — Ted Horn, owner of the Dixie Diner, Houston, Mississippi, December 1971
The Twenty-Dollar Bill
Ted Horn — who had been watching Larry Stewart through the entire meal with the small careful attention that small-town diner owners pay to the customers whose body language suggests something is wrong — walked up behind Larry as Larry was reaching for the door handle. He had, in his right hand, a twenty-dollar bill that had been in his apron pocket since opening that morning.
He tapped Larry on the shoulder. He held out the twenty. He said, in the small Mississippi drawl of a man who has been pulling small acts of mercy for half his life: "I believe you dropped this, sir."
Larry Stewart looked at the twenty-dollar bill. He looked at Ted Horn's face. He understood, with the small immediate clarity of a person who has just been forgiven for something he had not yet been caught doing, exactly what was happening. He took the bill. He used it to pay for his meal. He left the change as a tip. He drove the twenty-eight miles home to Bruce, Mississippi, that afternoon.
He never forgot that twenty-dollar bill. For the rest of his life — every single time he spoke about how he became the Secret Santa of Kansas City — he started the story with Ted Horn at the Dixie Diner.
December 1979: Eight Years Later, a Drive-In Restaurant in Kansas City
Between December 1971 and December 1979, Larry Stewart's life followed the kind of slow, halting upward arc that working-class Americans of his generation tended to follow when they had ambition and luck and were willing to move. He had left Mississippi. He had moved to Kansas City, Missouri, in 1973 — for reasons that, in his subsequent interviews, he tended to summarize as "a girl, then a job, then another job". He had worked in cable television sales. He had worked in long-distance telephone service. He had been fired twice. He had been re-hired twice. He had married a woman named Jane in 1976. He had a small house in the suburb of Lee's Summit. He was, by late 1979, 31 years old and just barely middle-class.
And he had, in early December 1979, been fired again, the week before Christmas, for the second year in a row.
The Drive-In on a Cold December Afternoon
The day he was fired the second time, Larry Stewart drove around Kansas City for several hours "to think". He stopped at a drive-in restaurant — the specific name of which he never publicly identified, though it is widely believed to have been the Sonic Drive-In on Blue Ridge Boulevard in Independence, Missouri — and ordered a burger and a Coke. He sat in his car in the parking space, eating slowly, listening to AM radio.
The carhop who brought his food — a young woman, maybe nineteen, with a name tag he later said he could no longer remember — was wearing a thin nylon work jacket. The temperature outside was approximately 28 degrees Fahrenheit. Her hands, when she handed him the tray, were visibly red and chapped from the cold.
Larry Stewart, sitting in his car in the parking space of a Kansas City drive-in restaurant on the afternoon he had been fired for the second Christmas in a row, looked at the carhop's red hands and thought — by his own later description — a single specific sentence:
" I think I got it bad. She's out there in this cold making nickels and dimes. — Larry Stewart, on the moment that started the tradition, in a November 2006 interview
He pulled out his wallet. He took out a twenty-dollar bill — the same denomination Ted Horn had handed him eight Decembers earlier. He handed it to her through the car window. He said, quietly, the line that had been said to him in Mississippi in 1971: "Keep the change."
The carhop, who had no idea who Larry Stewart was, stared at the twenty for a moment, then started to cry. She thanked him approximately fifteen times. She walked back toward the drive-in. Larry Stewart watched her in his rearview mirror as she walked. He sat in the car for several more minutes. And then, by his own later description, he made a decision — entirely on his own, with nobody watching — that he would do this every December for the rest of his life.
what Larry told nobody at the time
Larry Stewart did not tell his wife about the twenty-dollar bill at the drive-in. He did not tell his close friends. He did not tell anyone. The decision to spend every December of the rest of his life handing out cash to strangers was, in 1979, a small private resolution that he made alone in a car in a Sonic parking lot. He kept it private for the next twenty-seven years. The only people who knew Larry Stewart was the Secret Santa were the strangers he gave the money to — and even most of them did not know his name, his face (he wore sunglasses and a Santa hat by the early 1990s), or where he came from. They knew only that a man in a red coat had pulled up beside them on a December street in Kansas City and put a hundred dollars in their hand.
Twenty-Six Decembers of Anonymous Generosity
Between 1979 and 2006, Larry Stewart's small annual practice grew, slowly, into something that — in retrospect — was one of the most remarkable sustained acts of philanthropy in modern American history.
How Larry Stewart Made the Money
The money came, over the course of three decades, from two industries that boomed in the American Midwest in the 1980s and 1990s: cable television and long-distance telephone service. Larry had moved, in the early 1980s, from sales positions to ownership stakes in small regional providers. By the late 1980s, he was a partner in a Kansas City-based cable distribution company. By the mid-1990s — after the 1996 Telecommunications Act unlocked a wave of consolidation in his industry — he was, by every reasonable definition, a multi-millionaire.
He did not change his lifestyle significantly. He continued to live in the same modest house in Lee's Summit. He drove a regular American sedan. He continued to attend the same small Baptist church he had joined in 1974. The only major change in his finances, every December, was that he would withdraw, in cash, somewhere between $30,000 and $100,000 in hundred-dollar bills, depending on the year and his recent income.
The Specific Method
The method Larry Stewart developed, refined over twenty-six years, was almost completely consistent. He drove around Kansas City — and, after 1995, occasionally other American cities — in the first three weeks of December. He looked, specifically, for three categories of people: visibly low-income workers in the service industry (carhops, gas station attendants, parking lot workers, motel housekeepers); homeless men and women on visible streets; and small families he saw shopping at low-end stores or eating at fast-food restaurants who, by their body language and clothing, looked like Christmas was going to be difficult.
He approached them, one at a time. He said almost the same thing every time: "Merry Christmas. This is from Secret Santa." He pressed a hundred-dollar bill, sometimes two or three, into their hand. He turned and walked away before they could thank him or ask his name.
Why It Had to Be Cash
Larry Stewart had a specific, well-thought-out reason for why he used cash, and specifically hundred-dollar bills, rather than checks or gift cards or contributions to nonprofits. He explained it in dozens of interviews after his 2006 reveal:
"I wanted to give people something they didn't have to beg for, get in line for, or apply for. Something they could just put in their pocket and use that night. Cash, you don't have to qualify for. Cash is just a small immediate piece of trust that this person can spend on whatever they think they need." — Larry Stewart, November 2006
That sentence — "a small immediate piece of trust that this person can spend on whatever they think they need" — is, in some ways, the philosophical heart of the entire Secret Santa tradition. Larry Stewart was not, in any of his interviews, particularly interested in fixing the people he gave money to. He was not trying to lift them out of poverty. He was not trying to teach them about financial responsibility. He was trying, in a very specific small way, to honor what Ted Horn had done for him in 1971 — which was, fundamentally, to extend a small immediate piece of trust to a stranger who was having a bad day.
From Kansas City to Manhattan: The Trips Outside His Hometown
By the mid-1990s, Larry Stewart's annual Kansas City rounds had become, in his own internal accounting, "the easy part". He knew the city. He knew where to go. The hundred-dollar bills mostly just left his hand and disappeared into the small pockets of strangers without complication. Starting around 1995, he began, occasionally, to travel to other cities during December — and, after 2001, to travel to cities that had been struck by national tragedy.
New York City, September-October 2001
The most notable of these trips was to New York City in the immediate aftermath of the September 11, 2001, terrorist attacks. Larry Stewart flew to New York on his own dime, about three weeks after the attacks, with approximately $60,000 in hundred-dollar bills folded into the inside pocket of his coat. He spent four days walking through Lower Manhattan, particularly the neighborhoods around Ground Zero, handing out money to anyone who looked, in his judgment, like they were still emotionally or financially struggling.
He gave money to a fire department widow in Queens whose husband had died in the South Tower. He gave money to a Pakistani-American shopkeeper in Brooklyn whose business had collapsed because of post-9/11 racism. He gave money to a young EMT who had been on duty at the scene and who Larry recognized — by the small careful slowness of his movements at a coffee shop on Liberty Street — as someone in the early stages of post-traumatic stress.
Mississippi, September 2005 (Hurricane Katrina)
The other major outside-Kansas-City trip was to the Gulf Coast of Mississippi in September 2005, three weeks after Hurricane Katrina had flattened most of Biloxi, Gulfport, and the small coastal towns between them. Larry flew to New Orleans, rented a car, drove east into Mississippi, and spent five days handing out cash to the families he found sleeping in cars, in church gymnasiums, and in the small temporary FEMA trailers that had been set up along the coast.
He returned, on that trip, to his hometown of Bruce, Mississippi — which had not been directly affected by the hurricane, but where several extended family members had been displaced. He stopped at the Dixie Diner in Houston, Mississippi. Ted Horn — by then 81 years old, retired from running the diner, but still alive — was sitting at the counter that afternoon. Larry Stewart introduced himself to Ted Horn, for the first time in thirty-four years, and quietly told him what the twenty-dollar bill in 1971 had ultimately set in motion.
Ted Horn, who had had no idea, cried for almost an hour.
The "Elves": Tom Phillips, Buck O'Neil, George Brett
By the late 1990s, Larry Stewart's annual Kansas City rounds had grown too large for one person to manage alone. He began, very quietly, to enlist a small group of trusted friends to help him distribute cash. He called them — with the small affectionate self-mockery that characterized everything he did — his "elves."
Jackson County Sheriff Tom Phillips
The most consistent of the elves was Tom Phillips — at that point, a captain in the Jackson County Sheriff's Office in Kansas City; later, the sheriff himself. Larry had recruited Tom Phillips around 2000, primarily because — after several years of growing reach — Larry had had a few uncomfortable incidents in which recipients of money had tried to chase him down to ask for more. He needed, in his words, "somebody who knew how to handle a crowd."
Tom Phillips's first day as an elf, in December 2000, was the day he has subsequently described, in dozens of interviews, as "a life-changing experience." He went out with Larry for approximately six hours. He watched Larry hand somewhere between forty and fifty hundred-dollar bills to strangers across Kansas City. By the end of the day, Tom Phillips — a hardened career law enforcement officer who had seen most of what Kansas City had to offer — was, in his own description, "literally in tears."
"I was literally in tears at the end of the day, watching him hand out money to so many people. It was just fantastic. I said, 'I'm in for life.'" — Jackson County Sheriff Tom Phillips, 2007
The Other Elves
By the early 2000s, Larry Stewart had recruited four full-time elves and several occasional helpers. His most famous helpers included Buck O'Neil — the legendary Negro Leagues baseball player and Kansas City sports icon, who joined Larry on his rounds in 2002 and 2003; George Brett — the Kansas City Royals Hall of Famer, who occasionally rode along; and Dick Butkus, the legendary Chicago Bears linebacker, who joined Larry's annual Chicago trip starting in 2003 and continued to do so until Larry's death.
The elves were sworn to absolute secrecy. None of them, for twenty-five years, told a single reporter that Kansas City's Secret Santa was a Lee's Summit cable executive named Larry Stewart. Tom Phillips, in his subsequent recounting, has said that the question he was most often asked between 2001 and 2006 was, "Who is the Secret Santa?" — and that for six straight years, he gave the same answer: "I'm sworn to secrecy. You'll know when he wants you to know."
April 2006: The Diagnosis
The diagnosis came, as diagnoses often do, almost by accident.
Larry Stewart had been having persistent difficulty swallowing for several months. He had attributed it, initially, to a heavy cold and to the residual irritation from years of social drinking. His wife Jane had pressed him, repeatedly, to see his primary care physician. He had, in early April 2006, finally gone in. The doctor had ordered an endoscopy. The endoscopy had revealed a tumor at the junction of the esophagus and the stomach.
The diagnosis was stage IV esophageal cancer. The median survival, for that diagnosis in 2006, was approximately nine months. Larry Stewart was 57 years old. He had been the Secret Santa of Kansas City for twenty-six Decembers.
Why He Decided to Come Out
For most of the spring and summer of 2006, Larry told no one but his immediate family and Tom Phillips. He continued to plan, with the small distracted intensity of a man trying not to let dying interfere with December, his next round of Kansas City giving. He had pre-purchased approximately $100,000 in hundred-dollar bills from his bank in early July, in anticipation of the December trip.
And then, in early November 2006 — about seven months into his nine-month prognosis — Larry received a phone call from his lawyer. A national supermarket tabloid had been investigating the identity of Kansas City's Secret Santa for several months. They had, through a combination of bank records, surveillance of his Lee's Summit home, and interviews with anonymous sources, narrowed the field down to four possible men. They were, by early November 2006, approximately two weeks from publishing his name without his consent.
The Decision to Tell His Own Story
Larry Stewart spent a long evening — by Tom Phillips's later description, "the longest single phone call I have ever had with anyone in my life" — discussing the situation with his elves. The consensus was clear. If a tabloid was going to expose him anyway, it was better for him to control the story. If the story was going to be told, it should be told in a way that would inspire other people to do the same thing — rather than, in the typical tabloid framing, as a "millionaire's eccentric hobby."
On November 17, 2006, Larry Stewart held a press conference at his lawyer's office in downtown Kansas City. He was wearing a regular business suit. He had not yet started chemotherapy, though it was scheduled to begin the following week. He looked, to the assembled reporters, like a perfectly ordinary 58-year-old businessman. He read a short prepared statement.
December 2006: The Last Run
What happened next was, by every available account, the most intense and emotional five weeks of Larry Stewart's life.
Within twenty-four hours of his November 17 press conference, Larry Stewart was the subject of national television coverage. Within seventy-two hours, he had received more than 40,000 emails from Americans across the country. Oprah Winfrey called. Larry appeared on her show on November 30, 2006. He gave a half-dozen other major TV interviews — including The Dave Ramsey Show, where he explained, in his quiet small-town drawl, why the cash had always had to be cash.
The Final Trip Through Kansas City and Chicago
Starting on December 1, 2006, Larry Stewart — now visibly thinner from the early effects of chemotherapy, but still walking and driving on his own — went out for his last annual round. He was accompanied, on the first day, by Sheriff Tom Phillips. He distributed approximately $60,000 in Kansas City over the course of two weeks. He then flew, with Dick Butkus, to Chicago in mid-December. He distributed another $40,000 across the South Side over three days.
Total for the 2006 season: approximately $100,000 from Larry himself, plus another $65,000 from the four elves he had trained — Tom Phillips, Dick Butkus, and two others whose names were never publicly released.
January 12, 2007: The End
Larry Stewart died at his home in Lee's Summit, Missouri, on the afternoon of Friday, January 12, 2007, at approximately 2:00 PM Central Time. He was 58 years old. The cause of death was complications from esophageal cancer. Jackson County Sheriff Tom Phillips, who had become Larry's closest friend over the previous seven years, was at the house when he died. He gave the brief statement to the Associated Press that hit national newswires within an hour: "He was a wonderful person."
Larry Stewart's funeral was, at his family's request, private. There were approximately fifty people. Tom Phillips spoke. Dick Butkus flew in from Chicago. Buck O'Neil — who himself would die less than two months later, in March 2007 — sat in the front row.
By the Numbers: Twenty-Six Decembers of Larry Stewart
The Legacy: Society of Secret Santas, 2007–2026
Larry Stewart's most important act of preparation, in the months between his November 17 press conference and his January 12 death, was not financial. It was organizational.
He spent most of December 2006 and the first ten days of January 2007 training new Secret Santas. He recruited approximately twelve American business people — most of them quietly wealthy, most of them in the Midwest or the South — and walked each of them through, in person or by phone, the specific philosophy of what he had been doing for twenty-six years. He gave each of them his blessing to continue. He founded an informal nonprofit, registered in Missouri, called The Society of Secret Santas, whose website (secretsantausa.com) has continued to operate ever since.
2026: The Society Is Still Running
In December 2026 — twenty Decembers after Larry Stewart's last run — there are, according to The Society of Secret Santas, more than fifty active Secret Santas operating in American cities. Most of them are wealthy individuals who knew Larry personally or were inspired by his story. They distribute, collectively, somewhere between $1.5 million and $2 million per year in cash to strangers. They follow Larry's three rules: cash only, hundred-dollar bills, no recipient ever asked to identify themselves.
Sheriff Tom Phillips, now retired but still living in Kansas City, continues to ride along as an elf for the Kansas City-based Secret Santas every December. He is, in 2026, 78 years old. He has said in subsequent interviews that the annual rounds remain, to his great surprise, "the best week of every year of my life."
What Larry Stewart Said He Wanted
In one of his last extended interviews — recorded by the Dave Ramsey radio show in mid-December 2006, about a month before he died — Larry Stewart was asked what, ultimately, he hoped his story would mean to people.
"That's what we're here for. To help other people out. I don't have any more profound thing to say than that. If you can do it, do it. If you can do a small thing, do the small thing. If you can do a big thing, do the big thing. But for God's sake, do it before you find out you've only got nine months left." — Larry Stewart, December 2006
Frequently Asked Questions
Q: How much money did Larry Stewart give away?
Approximately $1.3 million dollars over twenty-six consecutive Decembers (1979–2006), almost entirely in $100 bills handed directly to strangers on the streets of Kansas City and a few other American cities. In his final season (December 2006), he personally distributed approximately $100,000 plus another $65,000 distributed by the four elves he had trained.
Q: What was the origin story?
In December 1971, a 23-year-old broke Larry Stewart attempted to "dine and dash" at the Dixie Diner in Houston, Mississippi. The owner, Ted Horn, noticed Larry's anxious demeanor and walked up behind him pretending to find a $20 bill on the floor, saying "I believe you dropped this, sir." Larry used the money to pay his bill. Eight years later, in December 1979, having just been fired the week before Christmas for the second year in a row, Larry gave $20 to a shivering carhop in Kansas City. That started the tradition.
Q: How did Larry Stewart make his money?
He made his fortune in cable television and long-distance telephone service in the Kansas City area in the 1980s and 1990s. After moving from sales positions to ownership stakes in regional providers, he became a partner in a Kansas City-based cable distribution company. By the late 1990s — following the 1996 Telecommunications Act consolidation wave — he was a multi-millionaire. He lived modestly in Lee's Summit, Missouri.
Q: Why didn't he just give the money to charity?
Larry Stewart had a specific philosophy. He believed in direct, immediate, no-strings-attached cash giving because it was "something people didn't have to beg for, get in line for, or apply for." He saw it as a "small immediate piece of trust" extended to a stranger having a bad day. He did also support nonprofits, but his Secret Santa tradition was specifically about restoring dignity through unconditional generosity.
Q: When did he reveal his identity?
November 17, 2006, at a press conference in his lawyer's office in downtown Kansas City. He had been diagnosed with stage IV esophageal cancer in April 2006. He decided to come out publicly because a national tabloid had identified him and was about to publish his name without consent. He used the platform to encourage other wealthy Americans to do the same kind of giving.
Q: When did he die?
Larry Stewart died on Friday, January 12, 2007, at approximately 2:00 PM Central Time, at his home in Lee's Summit, Missouri. He was 58 years old. The cause of death was complications from esophageal cancer. Jackson County Sheriff Tom Phillips was at the house when he died. The funeral was private, attended by approximately 50 people including Dick Butkus and Buck O'Neil.
Q: Who were his "elves"?
His four primary elves were Sheriff Tom Phillips (Jackson County, who joined in 2000), Dick Butkus (former Chicago Bears linebacker, joined in 2003 for the Chicago runs), and two others whose names were never publicly released. He was also occasionally accompanied by Buck O'Neil (Negro Leagues legend, 2002-2003) and George Brett (Kansas City Royals Hall of Famer). Oprah Winfrey hosted him on her show in November 2006.
Q: Did he travel outside Kansas City?
Yes, especially in his later years. Most notably to New York City in October 2001 (three weeks after 9/11), distributing approximately $60,000 to first responders, victims' families, and small business owners. And to the Mississippi Gulf Coast in September 2005, three weeks after Hurricane Katrina, distributing cash to displaced families. He also did annual Chicago runs starting in 2003 with Dick Butkus.
Q: Does the tradition continue today?
Yes. Larry Stewart founded The Society of Secret Santas in late 2006 to formally continue the tradition after his death. As of 2026, there are more than 50 active Secret Santas operating in American cities, collectively distributing $1.5-2 million per year in cash to strangers, following Larry's original three rules: cash only, $100 bills, complete anonymity for recipients.
Q: Did he meet Ted Horn again?
Yes. In September 2005, while passing through Mississippi on his Hurricane Katrina giving trip, Larry Stewart stopped at the Dixie Diner in Houston, Mississippi. Ted Horn — by then 81 years old, retired, but still alive — was sitting at the counter that afternoon. Larry introduced himself and told Ted what the 1971 $20 had set in motion. Ted Horn cried for almost an hour. He died approximately three years later.
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Sources & Further Reading
Primary news coverage:
- NBC News — "Mo. man known as Secret Santa dies at 58" (January 13, 2007)
- Southeast Missourian — Secret Santa $1.3M obituary
- Legacy.com — Larry Stewart Obituary
- Fox News — Secret Santa millionaire dies at 58
- Wikipedia — Larry Stewart (philanthropist) — definitive biographical entry
Society of Secret Santas continuation:
Cultural & geographic context:
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