Derek Torrellas photo
The following article was reported through a collaboration between the New Haven Independent and the Multimedia Journalism class at Southern Connecticut State University. The students are profiling small businesses around the New Haven area.
Bill Shields didn’t name himself the “Flag Man,” or more specifically, “The Flag Man of Long Wharf.”
It was customers, Shields said, who coined the term.
“The name of my business is Allegiance Flags,” he said. “But the whole Flag Man thing, it’s not me that really named it; it’s you guys that named it. You know, ‘look at the crazy flag man down there.’ I just said, ‘Hey, if the shoe fits, wear it,’ and I’ve been wearing it since 1995.”
Like the flag that survived a bombardment in the national anthem, the Flag Man weathers economic recessions and shifting traffic to stay in business.
The Beginning
Before Shields sold flags, or in his “former life,” as he called it, Shields was a professional printer. He printed everything from newspapers to junk mail to coupons.
Then his father-in-law in San Diego started telling him about the large swap meets that were held out there, and Shields decided to become a vendor more than 20 years ago.
Choosing to sell flags was no arbitrary choice.
“I’ve always had a geographical part of me,” Shields said. “I understood that a flag was more than just a piece of cloth, that it had a story to it.”
The Flag Man’s workday starts with the same routine Tuesday through Sunday. He parks the aging former U‑Haul truck on one end of the Long Wharf lot, forming an end to the long chain of Mexican food trucks. The northbound side of I‑95 is only 25 feet away, the sounds of diesel trucks and motorcycles sporadically drowning out conversation.
Shields unpacked four flag poles, and put one at each corner of his truck on customized brackets. At one point, while standing up the pole with an American and skull & crossbones flag, he imitated the well-known Marine flag raising on Iwo Jima. Though instead of Mount Suribachi, his backdrop is New Haven Harbor and the distant oil storage tanks.
Two more flagpoles representing countries from Europe, South America, and Africa were attached to the chain-link fence near the highway, and Shields took a seat on the open box end of the truck.
“I wait for the customers to come to me,” he said. “That’s just the way I am.”
A man in his mid-20s and a thick beard approached later in the day.
Ryan Michael, a child care worker for the state, asked Shields if he was selling flags for the May 2 Mayweather-Pacquiao boxing match. (They’re pictured at the top of the story.)
Shields told him no. The match was such a specific event that he didn’t carry a flag for it.
As Michael was leaving he stared up at the flags on top of the truck flapping in the breeze from the harbor. He stopped and turned around.
“With the ‘Don’t Tread on Me,’ that’s a military thing?” Michael said.
That was the original Marine Corps flag during the American Revolution, Shields said, pointing to the yellow flag in question. Shields answered more of Michal’s questions, including how the pro-Second Amendment “Come and Take it” emblem with an AR-15 rifle in the center is based on the original flag of Texas, though a cannon preceded the modern rifle.
Michael eventually bought the national flag of the Philippines — boxer Manny Pacquiao’s home country. It was the closest item to what Michael had come to the Flag Man truck looking for.
Sales come along in waves. Sometimes there are no customers for an hour or more. Then several people in quick succession will approach Shields looking for flags or roses, which he also sells.
Derek Torrellas photo
Shields admitted that he has to change for the future.
He mentioned several possibilities: “Maybe I might go for the weekends,” and “I’m thinking about getting a spot on the Internet.”
His business was affected by the change in exits on Long Wharf’s stretch of I‑95. Several years ago the exit was further northbound, and customers could see the vendors and then get off the exit. Now Exit 46 splits off from the highway before the colorful trucks are even visible.
Though the Flag Man truck is a “brick and mortar on wheels,” it isn’t so easy as parking and selling at a different spot.
“‘Itinerant vendor,’ they call us, although I call myself ‘a pillar of the community,’” Shields said.
It’s difficult to get established in a new community if there is a phobia of businesses on wheels. According to Shields, many other mobile vendors — particularly food trucks — are opportunists.
“A good food truck can destroy a good restaurant overnight,” he said. “A restaurant can’t compete with these guys.”
After 22 years, his “foot is in the door,” at the Long Wharf location. Shields said he has built up enough of a presence that people will remember that he’s there, despite the unfavorable traffic pattern.
While Shields doesn’t describe himself as an opportunist of the community, he acknowledges the fact that politics and conflict around the world are an advantage when more people come to him for flags. Last year, the Ukrainian flag was a good seller, he said.
In an earlier interview with Shields in August 2014, he was pragmatic about the business it provided.
“Flags are political devices,” he had said, “so war is my business, you see.”
Shields had then laughed off the comparison between him and Nicholas Cage’s gunrunning titular character in Lord of War.
“Only I do it visually,” Shields added.
