Larry Stewart, 58, from the Kansas City suburb of Lee's Summit, Mo., has been handing out $100 bills in impoverished sections of the Chicago area.
Stewart, who made national headlines this month when he revealed his true identity, earned his nickname by giving out thousands of dollars to strangers in need during the holidays.
"We've come all the way from Kansas City to see you, to wish you a Merry Christmas," Stewart told 29-year-old Eric Stewart during a stop Tuesday at a coin-operated laundry before pressing $100 into his hand.
On Wednesday he visited a disabled Chicago police officer in Joliet and then headed for Chicago's southwest side to hand out $100 bills.
"I'm trying to teach my kids that Christmas isn't about toys. It's about giving," said Marquetta Crawford, 29, a mother of three who received the $100 Tuesday when Stewart stopped by her restaurant in a neighborhood full of boarded-up buildings.
The businessman began giving out $5 and $10 bills decades ago. As Stewart made millions in cable television and long-distance telephone service, Secret Santa began passing out $100 bills — sometimes two or three at a time.
Stewart figures he has anonymously given out about $1.3 million over the years.
But the Santa stint may be coming to an end.
Doctors diagnosed Stewart with cancer in April. Now he's being treated aggressive chemotherapy that's stripped away his appetite and energy. He travels to Houston every two weeks to participate in a clinical trial.
With medical costs reaching more than $16,000 a month, he's concerned about his finances and his family.
Stewart hopes his story will instill in others a devotion to kindness while inspiring them to donate their time and money.
With his entourage in tow, Stewart came across a thrift shop, where the group approached Maria Ramirez and her 5-year-old granddaughter.
"I'm crying because I'm happy," said Ramirez, who had just lost her assembly line job. "It's a surprise. A very nice surprise."