Indigenous-owned Cigar Chief opens in Kingston on Canada Day across the street from history

[JohnS]

Indigenous-owned Cigar Chief opens in Kingston on Canada Day across the street from history

Gare Joyce - Published Jul 03, 2025 

Cigar Chief owner Matthew Greenwood and store manager Mark Tarnovetsky show their wares, opening for business on Canada Day in Kingston on Tuesday, July 1, 2025. Photo by Gare Joyce/Kingston Whig-Standard.

“Location, location, location” is the operative punchline about the three most important considerations in real estate and so it was for Matthew Greenwood, who opened his cigar shop on Canada Day.
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Greenwood, who lives in Tyendinaga Mohawk Territory, had a list of boxes that he had to check when looking to for a location to launch Cigar Chief Kingston.

“We wanted to be central, in a high-traffic area,” he said. “We needed enough space to accommodate a walk-in humidor with a humidifier. We were looking to offer customers fine coffee, so a counter space and a place to set up an espresso machine. And if there was history, so much the better.”

When he landed on a long vacant storefront at 340 King Street East, he covered the check list, especially on that last line item — the location had history in spades.

This wasn’t simply the limestone and brick construction, but its place in the nation’s history — directly across the street from what used to be the Sir John A. Macdonald, the pub that occupied the building where Canada’s first prime minister had his law office prior to Confederation.

The outcry over MacDonald’s authorship of the Indian Act led first to the pub removing his name from the tavern in 2018 before its closing in February 2021 and then to the removal of his statue in Kingston Park the following summer. Somehow, it seems fitting that an Indigenous-owned business would open in a place that Macdonald would have walked by on the way to work — not that it in anyway repairs the damage wrought, just that it signifies fairness and opportunities previously denied.

The 38-year-old Greenwood is a second-generation tobacconist — he started working in his father’s store in the Tyendinega Mohawk Territory when he was 13 years old. “I went to St. Lawrence is general arts for a year, but I never attended business school or anything like that,” he said.
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Greenwood brings an enthusiasm to his start-up that goes beyond the spreadsheets and sales projections and upholding traditions.

“Tobacco is an Indigenous product,” he said. “To us, it’s sacred plant medicine. It helps us communicate with the spirit. They say in 1492 Christopher Columbus found the Indigenous smoking rolled up tobacco leaves which they called Cohiba. That’s where the cigar Cohiba gets its name and that’s how tobacco was popularized in Europe, with Columbus bringing it back there.”

For now at least, Greenwood has no intention to take Cigar Chief Kingston online, for anything other than marketing and promotion.

“It’s important to make a personal connection with our customers, to give them a place to go and treat them how they deserve to be treated,” he said. “I look at stores that sell vinyl and I think music and tobacco retail overlap in that way — where you have a comfort level, a chance for social connection and share your love for something with others who love it, too.”

Greenwood’s father’s founded his business with the name Cigar Chief in the ’90s, but Matthew makes it clear that his King Street East operation is a “separate and distinct” operation.

“My father’s business is in a sovereign nation, an entirely different country,” Greenwood said. “Cigar Chief Kingston is a Canadian retail store in Canada and for us opening on Canada Day, we’re part of a bigger celebration.”

Source: https://www.thewhig.com/news/idigenous-owned-cigar-chief-opens-in-kingston-on-canada-day-across-the-street-from-history

[Wfriar]

I’ll have to check this B&M out when I am at the cottage next time. The reserve location was always hit or miss for Cuban stock for the past cpl years. Ordered my Canada RE dips from this place years ago. Still sitting on one vacuum sealed box…wish I had bought more! 😝

[Hammer Smokin']

I was gonna say, unless something has changed, they run a flourishing online retail facility. Natives are the only ones left allowed to do anything with cigars in Canada. 

[ChanceSchmerr]

Damn - I wish they had opened 20 years ago when I was in Military College in Kingston! I sure could have a used a few cigars in that final year LOL!

[benfica_77]

Cigar Chief have the best prices in Canada for legit CCs and even NCs but still paying a pretty penny...I wish them luck.