"It's going to be wild," promises Evander Preston as his friends Robert Nelson and Dino Dinerdo load up a silver 1987 Bentley with cardboard boxes. "The look on their faces is priceless."
After the last box is placed in the trunk, the trio hops into the car. Eddie St. Clair, Preston's longtime friend and employee, slips into the driver's seat. He is dressed in a full chauffeur's outfit.
The destination: Williams Park, the downtown St. Pete square where more than 100 homeless men and women spend their days lounging on benches or blankets in the grass.
The goal: to bring some holiday cheer to St. Pete's most downtrodden citizens.
The Bentley pulls into a parking space adjacent to the park and the four men step out. Nelson and Dinerdo slip two orange Home Depot bags over their shoulders and fill them with the contents of the boxes.
At first, the denizens of Williams Park don't seem to notice. Strangers offering handouts are not an unusual occurrence. But after the flash of a bottle in the midafternoon sun, the park's collective eyebrows raise. First are the young guys — they hop off their blankets and dash to the car. A handful of women follow. The older men reluctantly leave their shopping carts and stagger through the grass toward the quickly forming crowd.
Preston dips his hand into one of the bags and produces his gift: a half-pint bottle of aged Kentucky bourbon with a Thompson torpedo cigar taped to it. Both are decorated with embossed stickers of Preston's bearded face.
Eyes widen, smiles grow and hands outstretch.
Preston places the bottle in the hands of a stooping old fellow with craggy lines crisscrossing his face.
"This is excellent," the man cries. "This is wonderful."
There are 99 more bottles where that came from.
"Thanks, man, I really needed this."
"What a treat!"
"I'm telling you — you guys are the shit."
Jack Cross, a homeless Vietnam veteran and park regular, takes his bottle and looks Preston in the eye.
"Sir, you're going to heaven," he says.
Preston, 72, is no stranger to charity. As the eccentric owner of a renowned jewelry gallery and art studio in Pass-A-Grille, he's donated artwork to raise money for several organizations from the Make-A-Wish Foundation and Tampa's Big Cat Rescue. But four years ago, the goldsmith, chef and art collector wanted to do something for St. Pete's homeless population. Something, well, eccentric.
"At first, I thought it would be interesting to give out a six-pack and a cigar," he says over a glass of homemade sangria in his kitchen. "When I saw the excitement in their faces, it was inspirational."
After a few outings to various homeless enclaves around the city, he says, St. Pete's homeless began to recognize him. When he pulled up in his Bentley, they would run at him, jump on the car and hug him tightly.
Preston became the homeless' Santa Claus, a 6-foot-2 bearded Samaritan in a T-shirt and jeans who gave all the good street men and women what they really wanted for Christmas.
"Last time, a man came up and said, 'Thank you, this is so much better than a warm blanket,'" he recalls. "It's shocking how much everybody loves it."
Well, maybe not everyone. "I'm sure there are some people who don't like what we're doing," Preston says.
He's probably right.
"It's not something we would encourage," says Sarah Snyder, executive director of the Pinellas County Homeless Coalition. "I'm not terribly fond of smoking, but giving more alcohol to alcoholics is really not a good idea."
Preston says he simply wants St. Pete's homeless to enjoy the holidays just like he does — with a fine cigar and something to sip on.
"There is no motive to what we do," he says. "It's a gesture of goodwill."
It takes 10 minutes for Preston and his crew to pass out the 100 bottles of bourbon. As the goods dwindle, the crowd disperses to their regular perches around the park. It's a surreal scene: dozens of homeless sitting under trees and on blankets, smoking cigars and tipping their bottles toward the sky. On one bench, four older black men puff on their stogies and joke with each other.
"Homeless?" one of them says when asked how long he's been on the streets. "You can tell I ain't homeless — just look at the cigar I'm holding."
The benchwarmers roar in laughter.
Roger, a 63-year-old New Yorker, has been a regular at Williams Park for the last four years. He holds up his bottle of bourbon.
"What do you do when you have somebody in your house?" he asks. "You offer them a drink. So, even though we're here [in Williams Park], now I can offer my friends a drink."
Timothy Toth, another park regular, quipped, "It's the gift that keeps on warming."
With their gift bags empty, Preston and his friends return to the Bentley for the drive back to Pass-A-Grille. Preston says he recognized two people today. One man used to work on the beach; the other was a woman he went to high school with. She had crystal-blue eyes and wore different kinds of shoes.
"She's the one that killed me last time," Preston says.
Arriving back at the gallery, Preston steps out and holds up an unclaimed bottle.
"The beautiful part of it is this is not our last time," he says. "We'll be back again."
This article appears in Dec 5-11, 2007.