Today: Dec 07, 2024

Flag Man: selling flags on long warf since 1992

James Maleski, left, of Bridgeport, approaches Bill Shields to replace his old and worn American flag.
Bill Shields, left, emerges out of the back of his truck to hand James Maleski, of Bridgeport, a new American flag.
Bill Shields, left, emerges out of the back of his truck to hand James Maleski, of Bridgeport, a new American flag.

Derek Torrellas Photo Editor 

Amidst a sea of brightly colored Mexican food trucks parked between I-95 and the New Haven harbor, sat an aging U-Haul truck. Most of the food trucks flew two flags – the American and Mexican. But upon the white truck, over two-dozen flags fluttered on a coastal breeze. The truck is owned by Bill Shields, though he said most people don’t know his actual name. Instead, the New Haven area identifies him by another title – Flag Man.

“You guys named me,” Shields said. “I didn’t name myself, I just rolled with it.”

The naming occurred almost instantaneously after he started his business selling flags on Long Wharf Drive in 1992. From his customary spot, the Flag Man is easily visible to the tens of thousands of commuters that drive past on the highway everyday.

“Flag Man,” said Shields, “you know, it’s better than other names they’ve called me.”

The truck carries more than 700 different types of flags, Shields said, as well as flag poles and banners. He calls his business a “full service” stop for anyone looking to buy a flag. Shields is both boss and employee, joined only by one part-time worker, he said, as well as his wife who occasionally comes as “moral support.”

Shields said the reason he became a merchant of flags was because he has always been a geographical person.

medium shot
James Maleski, left, of Bridgeport, approaches Bill Shields to replace his old and worn American flag.

“I like the history, I like the symbolism,” said Shields. “You’re talking about something that can give you a message from a mile away, without hearing it.”

Shields turned and walked to the back of his truck when a customer approached with a question.

“By any chance, do you got a Ukrainian flag?”

“I do,” Shields said, and disappeared into his truck before returning a few moments later, handing the customer, Howard Fishman, the blue-and-yellow flag.

Fishman was buying the Ukrainian flag for his father, and said he has been a longtime customer of the Flag Man

It is a business that depends upon repeating customers, according to Shields. Construction on I-95 moved the northbound off-ramp so it is no longer possible to see the Flag Man truck before the exit. Shields said this compromised what had been a “strategic location,” and he has lost a lot of business in the years since.

Recognition, Shields said, still helps sell flags even with the reduced advantage of the neighboring highway.

“I’m like the furniture, they know I’m here,” said Shields.

Bill Shields -- more popularly known as Flag Man -- sits on the edge in the box of his truck while he waits for the next customer.
Bill Shields — more popularly known as Flag Man — sits on the edge in the box of his truck while he waits for the next customer.

Fishman came back several minutes later to return the flag. He apologized to Shields and said his brother told him he had bought one already.

“I’ll get another Ukrainian sooner or later. He’ll buy it,” Shields said with a grin as he went back into his truck with the returned flag.

Political unrest around the world – at the moment exemplified by Ukraine – has the potential to benefit the Flag Man’s line of work.

“I sell flags to both sides during any conflict,” said Shields. “Flags are political devices, so war is my business, you see.”

Shields said he does not take himself too seriously and laughed off the thought of him being like Nicholas Cage’s titular character in the film, “Lord of War,” who sold weapons to opposing sides. Shields smiled, and said the difference is the items he sells are visual.

James Namnoum, a Senior world language major, said that by chance he met Shields’ son while they were both at Marine Corps boot camp in 2000. Namnoum considers the Flag Man something of a landmark, he said, having always seen the unmistakable truck on Long Wharf for over two decades.

Shields, as the Flag Man, doesn’t consider himself a local celebrity. He said some of the attention is that people see the Flag Man in the current economy and scratch their heads.

“I’m like an anomaly to people,” Shields said. “They think ‘We lost K-Mart, and that guy is still down there’.”

Photo Credit: Derek Torrellas

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