Fred Mascolo, better known on-Island as Trader Fred, never passes on a good deal. He still remembers the first order he made for his Edgartown discount store, the eponymous Trader Fred’s: 2,500 pairs of Dunham boots, each to be priced at $24.99.

Now residing in an assisted living facility in Vineyard Haven and battling a terminal illness, Mr. Mascolo is still making deals. Just last week, a 53-foot shipping container full of new merchandise arrived at his shop at the Edgartown Triangle, ready to stock up for the busy summer season.

“This year, we’re ready to hopefully make it our best year ever,” Mr. Mascolo said. “A lot of my friends in the business have stepped up.”

In a bedside interview with the Gazette last week, Mr. Mascolo reflected on four decades as an Island businessman, and on his many years at the helm of the Vineyard’s only combined discount shop and cigar outlet.

Trader Fred was trained as a lawyer but took a turn to retail on the Island.

Mark Alan Lovewell

Trader Fred was trained as a lawyer but took a turn to retail on the Island.

Mark Alan Lovewell

“The whole store is based on an old-fashioned concept, a trading post,” he said, by way explaining his retail philosophy. “We sell everything.”

Mr. Mascolo first visited the Island in the 1970s at the age of 15 but didn’t land here full time until after graduating law school, during a period of soul-searching.

“As a lawyer you deal with everybody’s problems for the rest of your life and I didn’t want to do that,” he said.

He immediately fell in love with the close-knit Island community.

“It turns out you look forward to winter more than summer,” he said. “It’s all your close friends, you could make a fire on the beach — it was like our own private Island.”

Soon after moving here fulltime, Mr. Mascolo noticed that every time he went off-Island, friends would ask him to bring back lower-priced mainland goods.

“I decided it was time for a store that took care of the Island,” he said. “My main target was value.”

In the early days, he worked out of his Ford Econoline van, banking 350,000 miles while scouting goods. To get prices better than wholesale, Mr. Mascolo often secures low-cost merchandise from retailers going bankrupt.

He opened his first store, then on Upper Main street, in September of 1982.

“My feeling was, if I couldn’t make it over the winter, then I was going back to law,” he said. “Then the summer was just a big bonus.”

Everything at a discount, including cigars.

Ray Ewing

Everything at a discount, including cigars.

Ray Ewing

Mr. Mascolo painted the store’s sign himself, the one that still hangs today, as a cost saving measure.

“Every dollar saved is a dollar earned,” he explained.

It wasn’t only low-cost goods that made Trader Fred’s an Island destination. By the 1990s, Mr. Mascolo was the Island’s premier cigar seller. A Gazette article from 1995, framed on the wall of his humidor, outlines some of his most high-profile customers. Trader Fred’s supplied cigars to William F. Buckley Jr.’s Yacht during a stop on the Island, it reports, as well as becoming President Bill Clinton’s cigar seller during his Vineyard vacations.

His business dealings also extended far beyond Edgartown — Mr. Mascolo initially had locations in both Vineyard Haven and Oak Bluffs, and later opened nine store locations across New England. He also joined, and eventually purchased, Jane Brown Associates real estate agency, and served a long tenure on the Edgartown planning board.  

But for most Islanders, Mr. Mascolo became well known at his spot behind the counter at Trader Fred’s, manning the phone to secure new deals on merchandise. The shop is still packed floor-to-ceiling with merchandise, from discount shoes to fishing gear, beach umbrellas to wrapping paper.

His space behind the counter, however, has been vacant since September, when Mr. Mascolo had to be helicoptered off-Island for emergency surgery.

“Unfortunately, I am fighting a terminal Illness,” he said.

Mr. Mascolo only recently returned to the Island, now residing at the Henrietta Brewer House.

“This is as close to home as I can get without being home,” he said.

Returning to the Island, Mr. Mascolo said, has helped him keep a positive outlook.

“I’m just fighting the fight — I’ll never quit,” he said, adding that he has been emboldened by a steady stream of visitors. His many business associates, too, have all reached out to help him prepare for the upcoming retail season.

“Everyone, in every aspect of my life, has come back to help,” he said. “You couldn’t put a price on that.”