Cigar Chief co-owner and operator Matthew Greenwood, inside his operation in Tyendinaga Mohawk Territory. Greenwood’s father founded the business in 1997, and have grown it into one of the largest cigar retailers in the country. (Jan Murphy/Local Journalism Initiative Reporter) Jan Murphy, Local Journalism Initiative

Cigar Chief

What: Tyendinaga Mohawk Territory-based retail and online cigar store, featuring many of the world’s top cigar brands and more.

Where: 303 Airport Rd., Deseronto.

Hours: Monday to Friday, 9 a.m. to 7 p.m., Saturday and Sunday, 10 a.m. to 4 p.m.


Jan Murphy

Local Journalism Initiative Reporter

TYENDINAGA MOHAWK TERRITORY – “OK, everyone, please gather in the back! We won’t be long, I promise.”

It’s just before 9 a.m. on a Thursday, a time when most businesses are just unlocking their doors, or staff are just arriving for the day. That’s not the case inside Cigar Chief in Tyendinaga Mohawk Territory. Not on this day.

Its co-owner and operator, Matthew Greenwood, is ushering his busy staff into the break room for a quick meeting.

He explains that the cigar shop, a staple on the Reserve since 1997, has just totaled up a donation it will be unveiling to Quinte Mohawk School later that day.

Greenwood had pledged a percentage of one day’s gross sales, combined with collecting donations from clients and online shoppers, to help the school invest in a piece of technology called a STEAM lab (Science-Technology-Engineering-Arts-Math lab).

The excitement in Greenwood’s voice translated to a bounce in his step on this morning. No coffee required.

“We did an e-mail campaign, some social media awareness and pledged a percentage of sales for one day,” the 35-year-old Greenwood said as his staff gathered for the announcement. “It was so awesome.”

With music playing in the background, the bustling staff stopped production for a short moment so the boss could deliver some great news.

“We raised $11,000,” Greenwood announced, to immediate applause and smiles all around. And as quickly as they gathered, staff scattered to get back to their work at one of Canada’s largest and busiest cigar businesses.

“I wanted to give books to the school,” Greenwood admitted after the announcement. “When I grew up, that’s what I liked to do, read books.”

Instead, the school asked Greenwood to contribute to the purchase of the STEAM lab.

“It’s kind of the new way they’re trying to teach and learn, more hands on,” Greenwood explained. “They’re going to have things like water tester kits and iPads, modular seating … among other things.”

To be in a position to help within his community holds special meaning for Greenwood, who now operates the company that his father started in the 1990s. Such luxuries weren’t even on the minds of Indigenous children when he was growing up.

“It’s great for our people,” Greenwood said. “Our kids, for the last 100 years, they’ve been getting a lot of the short end of the stick as far as education goes. So to be able to do that and give them some of the opportunities and the benefits that other kids are having as far as education goes, you know that’s real, that’s awesome. The numbers came in this morning, and I’m just so excited. I haven’t even been able to tell the school yet.”

Cigar Chief itself started earnestly, with Bob Greenwood establishing the business in 1997, selling imported cigars online at first, then at small locations throughout the reserve, even operating a shop out of Picton, where his son, Matthew, helped.

“I love it so much it. I grew up in it. I used to go to school right over there by the airport,” Matthew Greenwood said, pointing across the street to the airport belonging to First Nations Technical Institute. “They had a high school for 20 to 30 Indigenous students. I would go to high school there and then after 2 p.m., I’d come in here and I’d work until 5, from the time I was 13 years old.”

Born in Vancouver, where his mother still lives, Greenwood split his time between Vancouver and Tyendinaga Mohawk Territory, working for his dad whenever he lived here. After his own son was born nearly six years ago, Greenwood returned to the Reserve to give his father some much earned free time and to take over the family business.

“Throughout my life, I got to come here, then go back (to Vancouver) to see my mom for a few years and this sort of thing, but only after I had been here for like 10 years of going every day, all day (at this business),” he said. “I’d sort of need a break, just to figure myself out. At one point, we had another store in Picton, years ago, where I was working seven days a week as well. I’d work here 9 to 5 and then I’d go there from 6 to 9 to close that up. So I’ve been doing it a long time.”

Greenwood’s father, who is now 72, remains involved with the business, but is enjoying the fruits of his labour as his son has assumed the day-to-day operations.

“I’m doing all the heavy lifting,” Matthew Greenwood said. “Dad’s 72 years old, so he’s enjoying life. That’s what he wants, that’s what I want for him to be doing so I’m doing as much of the heavy lifting as I can. He’s involved as much or as little as he wants to be.”


Greenwood is on the hunt for the perfect cigars for us to share while talking about his business. As we wind our way through the sprawling location, which boasts a massive retail area featuring thousands upon thousands of cigars, along with an enclosed walk-in humidor where the high-end Cuban cigars can be found, he’s greeting each staff member with a hello and calling them by name.

A contractor approaches, inquiring about getting a moment of Greenwood’s time. We follow him to the back, where they’ve have been busy installing state-of-the-art equipment that will control the humidity level in the entire facility, which is the most important feature for anything associated with cigars.

Already installed was a massive reverse osmosis water system, which looked like something out of a lab. Almost completed was the installation of a steam humidifier, the latest technology available, which will ensure ideal levels of humidity for cigars, which require the optimal temperature of 70 F and a humidity level of 70% to age best.

“We’re tapping into the water and we’re cleaning the water right here on site,” Greenwood explained of his massive investment. “This is going to give us the cleanest, purest water and is going to feed what they’re working on, the steam machines,” he said, pointing. “Even distilled water doesn’t take everything out because it distills it into a vapor, which rises to the top, then drips back down. There are some trace amounts of chemicals that will just stick around. They’ll turn to vapour and come back down. This is going to do all of that reverse osmosis so there won’t be anything in there. And so that’s what’s going to be feeding those steam machines.”

The new system immediately upgrades the entire process, and building.

“Now all of a sudden, we’ve gone from humidifying cigars with multiple humidifiers on the ground using distilled water from jugs, which is quite the process, to doing it all on site here. So this is not only better for the environment of course, but better for the cigars.”

It also eliminates the possibility of human error.

“Now we never have to worry about having to refill units when one unit goes empty or this particular unit was overfilled or doesn’t get filled up,” he said. “If one guy forgets to do it at the end of the day or something, it can cause harm. We’re really proud of this whole system that’s being installed.”


As we moved through the warehouse, where products were being shipped and received, we headed through a corridor where employees were busy preparing web orders, by far the largest part of Cigar Chief’s business, accounting for roughly 90% of all sales, Greenwood said.

He entered another room, where another walk-in humidor awaited. He disappeared inside, returning with two cigars for us to enjoy during our conversation. A huge part of Indigenous culture has always been and continues to be sharing with a visitor.

Greenwood’s cigar selection for our chat was the Padron 40th anniversary.

“Padron is one of the premier cigar brands that is not Cuban that can compete at the Cuban level,” he said, pointing to the label that listed it as the Cigar of the Year. “They’re serious. They get some serious reviews, but the construction is insane. The tobacco is aged a lot.”

The only thing Greenwood got more passionate about than raising money was when it came to discussing cigars.

“This is the first cigar to come up with a serial code on the band,” he said of our Padrons. “They were very serious and they were pretty much the first non-Cuban cigar company other than Davidoff to command a Cuban price point… really high end, super premium, super luxury, but they really back it up.”

Cigar Chief has been at its current location, at 303 Airport Rd., for the last 15 years, Greenwood said, where it sells and ships cigars throughout North America and to some foreign countries. Cigar Chief does not ship Cuban Cigars to the United States, where they remain illegal.

The building now housing Cigar Chief is formerly a Second World War Mohawk camp military base, Greenwood said, adding that pilots would train across the street at the airport.

“This was sort of the barracks, I believe,” he said. “After that, at one point they were making glasses in the building and it was used as an old industrial building. And then my dad moved the business here. When he moved it here, it was more of an office with a small store and now we’ve grown it into a bigger store as well as the office.”

As you step inside the main store, there are dozens of displays featuring countless brands of cigars. Shelving units at one end are filled with boxes of individual cigars, which can be purchased one at a time or in multiples, or by the box, while supplies last.

The original retail space still exists and features more displays and shelves of cigars, plus the large walk-in humidor containing whatever Cuban cigars are available on any given day.


While Cuban cigars remain the most widely known cigar in the world, they’re no longer the only major player in the industry, Greenwood noted. In fact, there are now three countries that are major players in the industry.

“The top three are Cuba, Nicaragua and Dominican,” he said.

“There are about 20 to 30, at most, Cuban brands in total. We used to carry pretty much all of them, but even throughout history, Havana House, the exclusive importer for Cuban cigars for Canada, has never carried all available Cuban brands. We’ll carry any ones that we can get, of course.”

Cuban cigars have the advantage of having been the first to establish a global presence, Greenwood said.

“The thing with Cuban cigars is only that they were the first to do it the best way,” he explained. “Cubans are aged for a longer time, usually about two years before they even touch them. With a Cohiba or a Trinidad, they get an additional year. That’s the reason why Cohibas and Trinidads are more expensive … they’re sitting there for a year longer. Padron is kind of the first after Cuba to do it the best in another country, other than Davidoff. And honestly, Padron and Davidoff have kind of been beating out Cubans a lot.

“With the Dominican, you’ve got some heavy hitters,” Greenwood continued. “You’ve got Davidoff, which we carry, you’ve got Arturo Fuente, which we’re the exclusive retailer for in Canada. There are not so many different manufacturers of Dominican cigars, maybe 10.

“The third biggest producer, Nicaragua, is somewhere in the middle. There are way more manufacturers, maybe 60 to 75 different factories producing cigars in Nicaragua, making brands like Oliva and Padron, what we’re smoking right now.”

Prices can vary widely when it comes to cigars. Some can be purchased for as low as $5 a piece all the way into the thousands. And as with most things, there are rare, extremely expensive cigars that are produced in limited quantities or using special leaves or processes that make them harder to get. But you’d be hard pressed to find anything pricier or rarer than the pre-Castro Cuban cigars, which are scattered around the world.

“These are anything that was made before 1959, when Fidel Castro took over Cuba,” Greenwood explained. “That’s when the embargo started. Fidel took over and he exiled any American from Cuba. Davidoff originally was a Cuban cigar, but when Fidel took over the country, Davidoff left to Switzerland and started making Dominican cigars with Dominican tobacco. They’re the first and only cigar brand from Cuba to ever leave. Cigars from before then, so that would be like 60-plus-year-old Cuban cigars, are in the tens of thousands of dollars for a box.”

A quick check on the Internet confirmed such cigars do still exist, but now sell in the hundreds of thousands for a box.


Cigar Chief has risen to be one of the largest cigar stores and retailers in the country in spite of strict federal and provincial regulations surrounding tobacco products, helped in part by the fact that Tyendinaga Mohawk Territory is a sovereign nation. But that doesn’t mean it still isn’t without its challenges, Greenwood said. Tobacco products imported into Canada are either adorned with frightening, oftentimes disturbing images, or in the case of cigars, adorned with plain packaging, which features an olive green box with small white writing.

“Everything is plain packaging,” Greenwood said. “You have no idea what you’re looking at in a lot of ways. A lot of the stuff is covered up, a lot of the tobacco you’re not even supposed to look at.”

The stringent regulations also deter tobacco importers, and even exporters, Greenwood added.

“I will tell you one thing, Cuba doesn’t like it because it’s they’re not making any more money off of this,” he said. “(Plain packaging) is costing them more money so what they’re doing is they’re not sending all of their different cigars. Where we used to get say, 25 brands, we probably right now are carrying 10 to 15. Five years ago, you could get Bolivar 1, 2 and 3. Now you can’t. They just don’t bring them into the country. And those aren’t the only ones. There are tons.”

In spite of the challenges of plain packaging, which targets tobacco but not alcohol in Canada, the cigar business is booming today, with many resorts and cities featuring cigar bars, and celebrities such as hip hop star Naz and athletes such as NHL Hall of Famer Martin Brodeur and MLB legend David Ortiz developing their own brands of cigars.

Cigar Chief itself now employs 15 full-time staff, plus seasonal staff during the busy season, Greenwood said.

“My dad worked so hard over the years at being different than some of the, I guess you’d call competition, for lack of a better word,” he said. The result has been the transformation from a home-based business into something of a cigar store giant.

“We’re blessed,” Greenwood said. “A lot of the walk-in traffic we get comes in from Toronto or Montreal, because Highway 401 is right there. We’re lucky there that some people are willing to take a few minutes out of their drive to stop in and see us. And over the years, through my dad’s dedication and hard work and being here, they’ve keep coming back and they know where to find us. We’re super blessed to have longtime customers like that. But we also, of course, have a lot of local people from the county and a lot of people from the Napanee area.”

As for online sales, the majority are shipped throughout Canada, Greenwood said.

“We have a fraction of customers from a couple of other countries, but yeah, mostly it’s just all Canada. We even have customers in Nunavut, Northwest Territories and the Yukon.”


Human beings have a long and storied history with tobacco, Greenwood said. Cigars were smoked long before cigarettes came along, but following their use during global conflicts, cigarettes became the accepted norm.

“Just look at those words: cigar-ette, cigar,” Greenwood said. “Cigarettes were rationed to soldiers during the First and Second World wars. It was a cigar that you could light up quickly and smoke. Then smoking really became fashionable and then, became, after the war, widely accepted. It was easier, it became the standard and everyone sort of forgot about the cigar.”

Over time, as the people began to seek reprieve from the fast-paced information age world of today, cigars, which Greenwood noted are not meant to be inhaled, have begun to emerge as a popular choice again.

“As you went farther away from the 1900s and closer to the 2000s, the world was just about producing everything, making money and doing as much work as possible, the age of workaholics,” Greenwood said. “I think people didn’t have the time to smoke a cigar so they would smoke cigarettes. They didn’t want to sit for half an hour or an hour. But I believe now that’s kind of going back the other way. That’s really what we’ve uncovered, is the allure of the cigars, to be able to sit for half an hour or an hour, a good chunk of time, and smoke something. I think what it does is it brings you back to the moment. It’s right from our Indigenous culture. This is a way to talk to the spirit world. That’s what this is.”

Unlike the majority of businesses across Canada, which enjoy the freedom to advertise and market, tobacco-related businesses face stringent laws and reduced freedoms.

“It’s illegal to advertise tobacco in Canada and that has really put handcuffs on,” Greenwood said, noting that even as a sovereign nation, the impacts are felt. “That’s the political environment my dad had to bring this business up in. We’re a sovereign nation inside of a country that’s completely against tobacco and makes it illegal to advertise.”

In spite of the stigma surrounding tobacco and stringent regulations, the cigar business continues to flourish.

“I look at it like the craft beer industry,” Greenwood said. “I love craft beer, what they’ve done with craft beer (is incredible). Twenty years ago, everyone was drinking Molson Canadian or LaBatt Blue. Now we’ve got all these intricate different craft beers and microbreweries and I feel that a lot of that culture in the young guys has sort of said ‘Hey, there’s craft beer so what about craft everything else?’ I think with cigars, we’ve started to see that mentality.”


Greenwood said he and his staff, dating all the way back to his father’s days, have worked hard to grow Cigar Chief into one of the world’s premier cigar destinations.

“People come into our store and they feel like a customer at any other store,” he said. “The problem is when you walk into most cigar stores, you’ll feel right away like a criminal. Everything’s locked up and everything’s hidden. You’re not. When a customer comes in here, they get to see the product themselves, like if they were in a fishing store. I know that kind of sounds corny, but making them feel at home when they come here is important. It’s like ‘Hey, this is your place, shop around.’ We even let you smoke a cigar when you shop if you want. How cool is that to be able to shop for a cigar while smoking a cigar? That’s what people deserve because they’re adults and I just feel like treating people like adults makes all difference.”

But as business has boomed, Greenwood said he hasn’t lost sight of the importance of giving back to his community, just as he had on this day.

“It means everything to me,” he said. “Twenty years ago, when everyone was so hard on tobacco in the country, I had a real tough time dealing with it, making a living off something that other people might say isn’t so good, especially being younger. But growing up, I’ve been able to see that there are benefits and that you can use it for good, that you can give back and be able to help others in the area.”

Getting an education, and having the tools necessary to get a good education, is of the utmost importance, Greenwood said, adding that he and his staff are so proud of the huge donation they were about to unveil to the school.

“Education is so important, as is having the tools to learn and to feel like you’re in the right place to learn, that you’re not falling behind everybody else,” he said. “I feel it is so important for kids to learn and be a part of the world and to be successful. You’ve got to have the tools to educate yourself and to be able to do something like that, using money from tobacco, even after so many years of people saying it was so bad, it just makes me realize it can’t be that bad because you can turn it into something really great, something really powerful for the community, for the families.”

Jan Murphy is a Local Journalism Initiative reporter who works out of the Belleville Intelligencer. The Local Journalism Initiative is funded by the Government of Canada.

By Jan Murphy, Local Journalism Initiative

Original Published on Mar 13, 2023 at 08:30

This item reprinted with permission from   Belleville Intelligencer   Toronto, Ontario
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