This year, he's still handing out money, but due to the economy, he says he just can't give out what he used to.
Instead, he's giving out more! One woman who got his mysterious gift counted it out: $450.
"Well, please don't make any misunderstanding - I'm a businessman and investor and I've taken a big hit just like everybody else has," Secret Santa told Hartman.
In fact, Santa's portfolio is down 44 percent. And yet he says: "This isn't the year to step back. Given the economy, this year is actually the year to step up."
By the time Christmas rolls around, Secret Santa will have given out close to $100,000, surprising more people in more places than ever before.
Starting with these Grants - Ulysses S. Grants. At DeLaSalle High School, a school for at-risk kids - all 200 got a $50 bill.
A waitress at lunch got $100, and said: "I guess there really is a Santa Claus!" So did everyone else who worked with her.
Even a random woman at a red light got at $100 bill.
And yet, this year especially, there is a method to his mad money.
"In our country we have a lot of people who make $8 to $10 an hour and they live in a $12-to-$14 an hour world," Santa said. "And so this year we are trying to concentrate on the working poor."
People like Teresa Miller - he found her working at a laundromat. Teresa needed $400 to pay her property tax.
Questa Corneele dropped her husband off at the buss station.
"Back to Oklahoma," Questa said.
Hartman asked her if that's where her husband works.
"That's where we used to live and he has to go back there so he can work and me and the kids can have a Christmas," Questa said.
One of Santa's elves gave Questa $200.
Santa and his helpers say people are always grateful. But this year, the reactions when some people see the money - it's almost like surrender. Grown men wail and burst into tears.
What a sobering economic indicator. And with so many like them out there, now, more than ever, we need more like him.
Fortunately, Secret Santa is cloning himself - recruiting other well-to-do businesspeople to be Secret Santas in their towns.
So far he's found leaders in Detroit, Charlotte, St. Louis, Phoenix and San Diego.