Freetown’s Habs fan, sort of.

Ajayi Decker traps the soccer ball under his right foot for a moment, before deciding where to pass it. He’s a natural centre-back; calm and quiet. The other young teens scramble and shout on the damp, gravelly road in Freetown’s hillside neighbourhood of Wilberforce. Ajayi and his friends idolize soccer stars at clubs like Arsenal, Liverpool and Barcelona. But Ajayi isn’t wearing a soccer jersey, he’s wearing a Habs jersey.

When I ask about it, he smiles. That Sierra Leone smile. Part shyness, part suspicion, mostly joy. He says his aunt bought him the jersey, but he’s not sure from where. He has no idea who the Montreal Canadiens are, either. The humidity in Freetown usually makes it feel like 40 degrees Celsius here, so when I try to explain hockey – ice hockey, I’m not quite sure where to begin.

Ajayi’s Canadiana is nothing unusual in Sierra Leone. I’ve seen a CBC cap for sale in the market town of Makeni, a Winnipeg Humane Society t-shirt in Freetown’s King Jimmy Market, and an elderly man wearing a white Leafs jersey in a remote beach community only accessible by boat.

More than 7,000 km from Wilberforce, a van creeps along a chilly street in the west end of Toronto. It’s going door-to-door, collecting blue plastic sacks, full of donated clothing. Printed on the bags: the logo for “Sick Kids”, and a message stating that more than 40% of the proceeds will go to the Toronto hospital. It’s not a bad day for the collector. There’s a sack outside about one-in-five houses. The value of what’s inside them is for someone else to worry about.

The used clothing industry is no thrifty matter. Canada exported US$182 million-worth of worn clothing in 2011, most of which was imported in the first place. We’re the fifth-largest used clothing exporter in the world, and it’s booming too. The industry has expanded by 60% in just six years.

The clothes are generally collected in three ways. Door-to-door bag donations, clothing bins and surplus goods at charity stores.

In recent years, parts of the industry have sometimes become less than charitable. Reports of misleading, or outdated labelling on bins, and even violence between for-profit collection companies has eroded public confidence in the practice.

Marc Nanthakumar says such incidents are disheartening. He is one of Canada’s biggest exporters of used clothing.

“It’s giving a bad feeling to the good people who have the good heart to donate stuff,” he says, standing in the middle of his noisy warehouse in Vaughan, Ontario.

“We pay our tax and give back to the community. We are giving in writing that we are not charitable. With us everything is in black and white.”

His business may not be a charity, but he knows that sharing his profits with those in need is the very key to his success. “We’ve made donations to North York General Hospital, Georgetown Hospital, Pickering Hospital,” he says.

In 2012, Nanthakumar was awarded a Queen Elizabeth II Diamond Jubilee Medal for his services to the community and charity work.

The 60-year-old Sri Lanka-native first moved to Canada in 1983. He worked for years at a car spare parts exporter, but in the early 1990s, a friend suggested that he use that experience to export clothes.

So, he and a business partner decided to buy used clothes, in bulk, and send them in containers to Ghana. When the ships would arrive in Africa, he would fly there on a Friday, unload the container, pay the duty, sell his clothes to wholesalers, transfer the money home, and be back in Canada for work on Monday morning.

An exhausting effort for a net profit of around $3,000 a job. Eventually, Nanthakumar decided to tell his partner he wanted to go out on his own. But he learned a valuable lesson about the industry when he followed their last shipment to Africa. When he opened the container, he found only rags. He’d been duped by his partner.

“When I opened it in Ghana, everyone started screaming at me.” He laughs now, but you can tell it shook him at the time. “I gave all the money back. At least my life was safe. I lost almost $20,000. Whatever I had earned was gone. Plus I didn’t have a buyer anymore.”

His wife Judy told him not to give up. Soon, they were spending evenings in their garage, sorting clothes, bought from the Salvation Army at 4¢/lb.. The couple invested in a baby monitor, to keep an ear on their toddler Dushan, while they prepared the shipments. To make ends meet, Nanthakumar also took a job delivering morning newspapers.

The clothing business quickly grew, but Nanthakumar says the Salvation Army soon raised their selling price. At that point he decided to make use of his paper delivery service by dropping-off clothing bags with the newspapers, and getting a licence to pick-up door-to-door.

Suddenly he was getting the clothing for free, but says he would voluntarily donate to local hospitals, wherever he made collections. It was a recipe that worked.

Today, his company, DYN Exports, ships to 28 countries, mostly in Africa. It still collects door-to-door, but also from designated clothing bins, and buys from the U.S. branches of The Salvation Army and Goodwill. The Salvation Army in Canada no longer sells its unsold clothing for export. Goodwill says it tries to sell all donated clothes within Canada, but a portion of its donated clothing does end up being sold to clothing recyclers.

One of the big partnerships for DYN is with Sick Kids. The company collects under the hospital’s name, and passes-on 41% of the sales. For Sick Kids, it’s pretty much money for nothing. For Nanthakumar, it’s a respected charity brand that fills those blue sacks. Nanthakumar says other hospitals in the Toronto area now want in on the action, and similar deals are on the way. DYN also collects on behalf of the Ontario Volunteer Emergency Response Team (OVERT).

Up until 2013, DYN employed over 200 people, and Nanthakumar believes it was then one of the biggest business of its type in the world. A setback came in the form a of leaky roof that destroyed his old warehouse and much of the clothing inside.

His workforce is now just 50, and he’s slowly rebuilding the business at a newer facility. He says the whole episode cost him over $2-million, but previous successes meant he could swallow the loss.

That healthy balance sheet is down to more than just old t-shirts and jeans. Even though DYN specifies it only wants used clothing, pretty much anything you can imagine ends up on the curb, or in the bins. Bikes, plates, mats, pillows, broken toys, single shoes, clothes hangers, and tonnes upon tonnes of torn, or damaged clothing.

“But everything can be sold, or recycled,” says Nanthakumar. “No garbage ends up in landfill. We find 70-to-80% is useable [as clothing]. Then, wool and synthetic materials go to India to take the yarn out, to make carpets and table mats. The rags, we cut them and ship them to a company in Brooklyn, for use in the automotive industry. Toys, we can ship to Sri Lanka, Iran, Iraq. We have never a problem, selling this stuff.”

He says he takes pride in making sure as little as possible gets thrown away. In fact, he says when he ships a container full of low-standard clothing, pillows and blankets to places like Pakistan, he only gets paid around $4,000. Much less than it costs him to prepare and send it.

“We are doing it, because we feel sometimes you have to lose, but it’s going to right place. Somewhere, someone can use it. We even ship single shoes. You think, ‘who has a use for a single shoe?’ In Pakistan they use it, because in certain areas they are so hard to find. My labour is costing me more than $10,000, but at least someone is using it.”

At the other end of the scale, vintage clothes are what really pays. His most lucrative international market is, of all places, South Korea. A 40-foot container of Macklemore’s gold will go for up to $80,000.

Buyers also drive up from Toronto thrift stores to sift through his mini mountains of clothes. He knows the buyers make huge mark-ups, but he says he doesn’t have the time or the knowledge to spot a pair of 1971 Levi 501s. He says that’s exactly what slipped through his fingers around 10 years ago. The store owner bought a pair of jeans at DYN for $10, and sold them on for $5,000.

But Africa remains the main market for the used clothing export business in Canada. At exporters like DYN, clothing is sorted into labelled bails before it leaves: “Men’s white long-sleeve shirts”, “children’s shorts”, “women’s short-sleeve blouses”, “baseball caps”, “flip-flops”. They’re then packed into containers, floor-to-roof, not an inch to spare.

The shipments take six-to-eight weeks to make their way from Vaughan to places like Mombasa, Dakar and Douala. When the bails are unloaded from the shipping container, it’s not long before they make their way to the market. Wholesalers sell bails to buyers. The buyers unwrap the contents and sell to market traders, piece-by-piece.

The African appetite for clothes from North America and Europe is down to two factors: quality and fashion.

In Canada, some may complain about the prevalence of low-quality clothing made in Asia, but relatively speaking, we get the good stuff, and because it lasts, that’s what we eventually donate. In Africa, new, imported clothing generally comes from China, and is of a lower quality.

Alim Bangura sells men’s t-shirts from a stall in Freetown, Sierra Leone. He, and everyone in the market, refers to the new Chinese-made clothing as “Guinea-Guinea”, named after the neighbouring country through which the clothes are imported.

“Used clothes will last,” he says. “Guinea-Guinea will take about one month before you can not wear it. It will not last.”

Bangura, who buys shirts for about $2 a-piece, sells them on for double that. He says the second reason people want Canadian used clothes is to stand out from the crowd.

“Normally the bails come with designs you will never see twice. Never see it again,” he laughs. “But with Guinea-Guinea, you see it everywhere. You can not swagger with it!”

At a neighbouring market stall, another trader butts in. Alpha Sesay says the most popular clothes of all are from Britain.

“We think British people are more stylish than Canadians,” says the men’s t-shirt seller. “The difference is not that vast. People just prefer to put on British clothes for one reason or another.”

Union Jack stickers adorn hundreds of taxis and mini-buses in the capital of this former colony. Just about everyone follows English Premier League soccer. Add to that the fact that the British Army helped end the hellish 11-year civil conflict in 2002, and the Sierra Leonean respect for British fashion is more than understandable.

Marc Nanthakumar is not too worried about competition from those stylish Brits.

“In the long run, I think I can create thousands of jobs. Maybe not just in Canada. But in third world countries,” he says. “If I had capacity I could make 10-times more business in a year.”

DYN’s new president quietly nods in agreement. The student of electrical engineering should know. Dushan has been a witness to this rags-to-riches story for every one of his 22 years.

And, up on that hillside road, overlooking the Atlantic, Ajayi is happy to stick with Canada and the Canadiens too. When I push him for an answer on why he wears the heavy, polyester jersey so often, I see that smile break out again.

“I think I just like the colours.”