Santa Claus is (Still) Coming to Town

Meet a 78-year-old Rockford man who’s spent almost 50 years sharing Christmas cheer with local children. He’s dressed, of course, as the one and only Santa Claus.

For Sherwood Anderson, there’s no greater time of the year than the festive Christmas season. Spending time with loved ones. Seeing the smiles on children’s faces as they open gifts. Oh, and dressing up in a red suit with white fur collar and cuffs.
“I always believed in Santa Claus,” says the Rockford native. “I’ll never forget that first basketball Santa put under my tree.”
At 78, Anderson still believes. That’s why, for the past 50-plus years, this insurance-salesman-by-day dons a Santa Claus costume every Christmas Eve and spends hours delivering presents to good little boys and girls throughout the Rockford area. It’s a love affair that began in the military.
In 1960, Anderson was an Air Force lieutenant at Homestead Air Force base in Homestead, Fla. Every 28 days, the B-52 bomber pilots had to fly a mission, leaving behind spouses and children, even during the Christmas season. That’s when Anderson, who was single at the time, rolled up his sleeves and got busy.
“My commander suggested that some of us single guys step up and play Santa Claus, bringing good tidings to those families whose fathers were gone on missions,” he says. “The officers chipped in to buy gifts that myself and another officer delivered on Christmas Eve night. If they left their porch light on, we’d knock on the door and leave a few presents behind. We’d cover seven or eight blocks in a night. It was fun.”
After his stint in the service was complete, Anderson returned home to Rockford, where he began his insurance career and continued his role as Santa Claus. “Why not?” he asks. “Many of my clients had young children. It seemed like the right thing to do.”
So every Christmas Eve, he’d dressed up as Santa, and drive to the homes of a few clients, dropping off gifts. These days, he’s delivering to second and third generations of family members.
Over the years, word spread about the Santa suit-wearing insurance salesman. Eventually, he started making visits to nursing homes, hospitals and children’s homes, all asking Santa to stop by and lift the spirits of people who were isolated or ailing.
In his heyday, Anderson made as many as 25 stops in one night. These days, he’s cut back to about 10. “I’m getting old,” he says. “I can’t lift all those presents like I used to.”
Anderson says he played Santa at home for his wife and their two daughters until the girls were about 6 or 7. “That’s when they were on the fence about Santa,” he says.
His family had no problem with Dad being gone on Christmas Eve. “It’s not about Santa being in our living room, it’s about him helping multiple kids,” says daughter Michelle Griesman, who rides along with Anderson in his black Yukon, which he affectionately refers to as his ‘sleigh.’ “Our family knew he was doing it for a good cause. Too many times, we only think about the presents at Christmas time and not about service or helping other people. My dad loves doing this, and seeing the joy on the children’s faces. It’s very touching.”
Anderson begins his Christmas Eve route around 3 p.m. and runs until 9:30 p.m., with stops in Rockford and neighboring communities. Many times, his host will leave presents in the garage or near the front door for Anderson to deliver. He’s greeted by enthusiastic adults and children alike.
The visit is brief. He greets people, distributes the presents, and poses for pictures, before saying his goodbyes. Santa declines any beverages – milk or otherwise – but seldom refuses his favorite cookie, oatmeal. Each visit lasts no more than 10 or 15 minutes. “I always tell the kids that Santa’s in a hurry,” he says. “Kids are pretty observant. The longer I’m there, the better chance they have of figuring things out.”
Anderson doesn’t accept any monetary gifts for his good deeds. If a family is insistent, he’ll donate the money to a local charity. “I always give it to someone in need,” he says. “I know I’m away from my family on Christmas Eve for six or seven hours, but the holidays are about helping others. This is my passion. I get more out of doing this than by sitting around on Christmas Eve.”
Over the years, Anderson has even started to resemble Kris Kringle, with his salt and pepper hair and gray mustache. A former runner, Anderson now stands at 6-foot 2-inches and, at 240 pounds, teases that he’s grown into the Santa persona. “I used to wear a pillow under the suit,” he says. “Now I don’t need to.”
Anderson special orders his costume and beard every five to seven years. When he’s finished with a suit, he donates the old one to a local charity.
For the past 24 years, Anderson has visited Larry and Gerri Phippen’s home to entertain their eight grandchildren, who range in age from 5 to 26. A friend recommended Anderson to the Phippens. “He’s wonderful,” Gerri says. “He always makes it special for the little ones. All these years and the kids are still in awe when he comes through that front door. He’s the perfect Santa Claus.”
It’s about the kids for Anderson. He gets a kick out of the things children say and do when he arrives at the front door. “I had one little girl, whose family had recently moved to the area, come to the door and say, ‘How did you find us?’ he says.
Every so often, he comes across a child who doesn’t believe in Santa Claus. “I started putting one boy’s gifts back in the box when he screamed, ‘I didn’t say it Santa. Some other kids said you weren’t real.’”
Sherwood observes, “Most kids want to believe.”
One of the more difficult stops Anderson makes is to the home of a terminally ill child. “That’s tough to see; it gets to me,” he says. “There’s always someone out there who has it worse than I do. We’re all blessed more than we realize.”
That’s why Anderson will go wherever he’s needed. Saying no isn’t part of his vocabulary. Because of his generosity, he has developed many solid friendships over the years. “I have memories that will last a lifetime,” he says. “I get more out of it than the kids do. They thank me and hug me. They love Santa Claus.”
As for the future, Anderson would like to groom his eventual replacement. Better yet, he’d like to recruit four or five more jolly fellows so they could cover more ground and spread more good tidings.
His fan club is rooting for Anderson to stick around for as long as possible.
“It wouldn’t be Christmas without him,” says Phippen. “The kids, even the older ones, would be devastated without him here. The teenagers never say a word. To them, he really is Santa Claus.”