Calvert case suspect Dennis Gerwing: Was he a good person who did bad things?

Dennis Gerwing was a good friend to many. He was the CFO of a successful company, owned a large yacht and had homes in Columbia and on the island. He was a wine aficionado who enjoyed gambling and loved to entertain friends. He was known as a good person, but good people can sometimes do bad things. He had money problems, and John and Elizabeth Calvert expected he was stealing from them. He was likely the last person to see them before their disappearance. This is the second of five excerpts from a new book on the disappearance of Calverts: “Deceit, Disappearance & Death on Hilton Head Island” by Charlie Ryan and island author Pamela Martin Ovens.

Dennis Ray Gerwing had been on Hilton Head twenty years when his troubles began to magnify. He did not fit the persona of a killer or a cheat. It was hard to find any islander who did not like the cherubic Gerwing. Most who knew or encountered him said he was the quintessential “hail-fellow, well-met” guy.

Everyone remembered Dennis’s laugh— “That great laugh,” one friend said. Another Islander who loved Dennis Gerwing remembered him as having, “A smile and a glowing face.”

Gerwing enjoyed life and the people in it. That smile his friends remembered lit up any room and folks looked forward to seeing him enter that room. Gerwing’s obituary described him as, “A kind and generous person who helped many struggling people build better lives.”

Dennis, his brother Fred, and sister Pat, grew up in Louisville, Ken., children of a machinist, Morris, and Mary Helen, a schoolteacher.

Morris spoke to Mary Helen outside her church one day. He was on a Western Union bicycle, and he had a telegram for “the girl in the green coat.” The telegram asked Mary Helen to marry him. Mary Helen died of a brain aneurysm in 2006. Dennis’s father, Morris, died of dementia following Dennis’ death.

A hardworking young man with a broad grin, Dennis graduated from Bellarmine University in Louisville. While in college he married Dale Anderson from Louisville, who was studying to be a lawyer. The marriage lasted only one year, supposedly because they were separated — she remained in law school, and Dennis moved for employment purposes.

Nancy Barry, Dennis’s first girlfriend after his marriage ended, believed that Dennis, who always called his mother Mary Helen, lost his moral compass when his mother died. Leaving Louisville was not difficult for Dennis, Nancy said — Dennis had found Louisville a town where it was difficult for him to enter “high society”.

“Dennis liked ‘old money,’” she said, “and he wanted to be accepted into that society.”

So, he moved on.

After he achieved his goal of becoming a certified public accountant, Arthur Andersen hired Dennis for its Indianapolis office. His work ethic quickly brought him to the attention of his superiors, and they offered him an opportunity to move up — to their offices in Denver.

The Denver office did accounting work for Ned Heizer at Resorts International, a company run by John Hemphill and John Platt. Hemphill and Platt subsequently hired Dennis as CFO of Vacation Resorts on Hilton Head. Dennis eagerly accepted the offer to move to the land of milk and honey. He had arrived in what he considered to be high society.

One year later, Vacation Resorts was sold to Ginn Holdings Corporation, and Dennis found himself working as head of finance and administration for them. Dennis rolled with the punches when real estate dominoes began to fall in the midst of a national recession, and the Ginn company was acquired by Luke M. Taylor Jr. and Philip Schwab. He stayed on with the Taylor-Schwab Company, known as Hilton Head Holdings.

There, Dennis remained for a short while, but he would soon become a co-founder of The Club Group — a company built out of the ashes of Ginn Holdings Corporation.

Dennis’ girlfriend of 22 years, Nancy Barry spoke of their relationship as “life partners.” Nancy described Dennis as “Mr. Wonderful.” She stayed on Hilton Head for two years before moving to her hometown of Columbia — to live in Dennis’ house. Dennis, who fondly nicknamed Nancy his “Big Girl”, stayed on Hilton Head, but the romance continued. Later, he would christen his new boat the Big Girl, in honor of Nancy.

“Dennis was a good man and always did the right thing,” she said. “He supported me working and having my own life. I worked for an orthopedic surgeon for 13 years and a neurosurgeon for 17 years.” She added, “Dennis was brilliant, chauvinistic, and thoroughly enthralled by (Sea Pines founder) Charles E. Fraser.”

She told a friend that Dennis never used drugs. “He was 100 percent anti-drug. He loved his red wine,” Nancy said.

Nancy last heard from Dennis on Monday, March 10. It was around 4:30 pm and Dennis said he was calling from his attorney’s office. He said he would not be coming to Columbia because “things weren’t looking good.” He told Nancy he was a “person of interest” and that he might be the last person to have seen the Calverts alive.

Dennis had prospered in his work on Hilton Head and purchased a home in one of the toniest areas of the resort paradise. The narrow strip at the south end of the island where he bought was called “Calibogue Cay” — uber-expensive real estate with multi-million-dollar homes that featured state-of-the-art docking facilities for the owners’ fishing boats and high-end yachts.

Dennis later sold the waterfront home he owned on Calibogue Cay and moved to Hilton Head Plantation and into a $430,000 residence on the north end of the island. In his home, he placed a myriad of pictures taken with buddies on trips to the Arctic Circle, Patagonia, the Sahara, and other distant locales. Dennis was an exceptional photographer, and many of his photos were in the pages of National Geographic Magazine.

Gerwing’s older brother, Fred, said, “Dennis was obsessive/compulsive in some areas of his life.” Asked about The Club Group losses, Fred said he had to assume they were a result of Dennis’ gambling. Fred said he thought that was confined to casinos, that he had never heard Dennis speak of bookmaking nor had he known him to bet. He said he found no evidence of that in searching through Dennis’s personal effects.

Dennis did, Fred said, invest heavily in the stock market — including one penny stock that went south on him. “Dennis took escrow accounts and was to put 2 percent into the stock market. He invested in different stocks, hoping to make more money and keep the profits. That did not work because most of the stocks he chose did not make any money,” Fred said.

Most people knew Dennis Gerwing and John Calvert to be very close friends.

Dennis Gerwing was 54 years old when he died.

This story was originally published March 6, 2018 at 6:00 AM with the headline "Calvert case suspect Dennis Gerwing: Was he a good person who did bad things?."