• Flor de Oliva, the cigar that started the entire Oliva brand, is now officially launching in Canada in a new Cabinet Edition box.

• We sat down with Brian Shapiro, international sales manager for Oliva Cigar Company and a fourth generation cigar man himself, to talk about the launch, the brand's history, and where Flor de Oliva fits next to Serie V and Melanio.

• Nicaragua has gone from the least respected cigar producing country in the world to the number one export country, and Brian was there for most of that climb.

• Every cigar purchase during the promotion gets you a raffle ticket for the exclusive Oliva Soccer Ball Humidor, loaded with 24 Serie V Melanio cigars aged three years and currently reselling for up to $1,000 online.

The cigar that built Oliva is finally here

Before there was a Serie V, before there was a Melanio, before there was a soccer ball humidor reselling for four figures on eBay, there was Flor de Oliva. It was the cigar the Oliva family sold out of the trunk of their cars in 1995, and it is the reason everything else exists. This week, that same cigar officially lands in Canada, dressed up in a new box for the occasion.

We had the chance to sit down with Brian Shapiro, Oliva's international sales manager, for an in-depth conversation about that launch and about the brand as a whole. Brian is not just an Oliva executive. He is fourth generation in the cigar business himself, tracing back to 1922 when his family opened a candy and smoke shop in New York City. He still co-owns a cigar shop and licensed factory in Connecticut today, which means he has spent his entire career on both sides of the counter, as a retailer and as the man who helped take a Nicaraguan bundle brand into more than 45 countries.

Here is what we learned, and what it means for Canadian cigar smokers picking up Flor de Oliva for the first time. You can watch the full interview on our YouTube channel, or press play below.

From the trunk of a car to Nicaragua's number one export

Oliva's story starts with tobacco, not cigars. The family had been growing in Nicaragua for decades before Gilberto Oliva and his son Jose officially launched the Gilberto Oliva brand in 1995, renamed Oliva a year later. Brian was blunt about how far the brand has come since then.

"The cigar manufacturing goes back to 1995, when the company started, as we like to tell the story, selling bundle cigars out of the trunk of their cars," he told us.

The turning point came in 2007, when the Serie V picked up its first major recognition from Cigar Aficionado, a moment Brian says shifted how the industry saw the company. "That was a big deal for our company internationally," he said, "because readers, cigar smokers would read Cigar Aficionado and see that. That was important to us to have that notoriety and be brought up from, hey, we're a bundle cigar company, to a premium" one.

What is easy to forget now is where Nicaragua actually stood at the time. Brian put it plainly: "Nicaragua was not thought of at the top of the food chain in terms of cigar countries. At the time it was Cuba internationally, of course, Dominican Republic would be second, Honduras probably third, and Nicaragua dead last." Today, by his account, Nicaragua is the number one cigar exporting country in the world. Every Flor de Oliva, Serie V, and Melanio you buy from Smoke Master is a product of that climb.

The retailer who took Oliva global

Brian's own path into Oliva is almost as good a story as the brand's. He met Jose Oliva in 2004 on an unannounced stop into the Miami Lakes office while traveling with his father on family business. The two became close friends, and in 2005 Brian officially came on as Oliva's first in-house head of sales, at a time when the brand relied mostly on regional brokers.

His international breakthrough happened almost by accident. Brian had been visiting the Netherlands since the late 1980s for family reasons, spending time in cigar shops purely as a customer. Years later, a contact he had made there, Sasja van Horssen, became the first international importer of Oliva cigars around 2006, which Brian calls "the birth of Oliva internationally."

Getting into European duty free was its own slow climb. Brian remembers that around 2007, Oliva's German distributor had no real demand for the brand in duty free shops, which at the time were dominated almost entirely by Cuban brands and Davidoff. "Fast forward all these years later," he said, "I walk into duty free shops around the world, you find Oliva owns the shops. It carries a lot of weight." That growth accelerated further after Oliva's 2016 sale, when new ownership brought an existing duty free infrastructure that Oliva could plug straight into.

The 2016 sale that changed everything

In 2016, the Oliva family sold the company to Fred Vandermarliere, whose company J. Cortes has been in business for roughly a century. Brian is candid about why that deal worked when it could easily have gone the other way.

"He realized you don't need to turn a company upside down to do better," Brian said of Fred. "He realized we had a lot of good people, we had a lot of good things. He said, let's improve upon what we have, but let's leave the things alone that are going great."

What makes Oliva different from a lot of acquired cigar brands, in Brian's view, is that it stayed a family business rather than becoming a corporate line item. Jose Oliva still has an office at the company and goes in daily, his father remains involved, and Brian says the team is still constantly checking in with each other on decisions. "It's still, at the end of the day, it's Fred's family," he said. "It's a real group experience."

Serie V or Melanio: Brian gives us his real answer

Every retailer gets asked this question, so we put it directly to the man who has spent two decades selling both. The Melanio, released a few years before it, won Cigar Aficionado's number one Cigar of the Year in 2014, and remains Oliva's most decorated release. But Brian's actual favorite is the Serie V.

"It's one of the most fantastic expressions of Habano I've ever smoked in my life," he told us. When we pushed further, asking about his single favorite smoke across every brand he has ever tried, not just Oliva's own lineup, his answer was immediate: the Serie V Churchill. "It's my favorite cigar that I've ever smoked, and you know, not just in the Oliva line, that's my go to. I have them in my bag."

His explanation for why the two cigars feel so different comes down to leaf, not just marketing. He credits the Serie V with "the perfect amount of ligero," giving it a fuller kick without becoming overpowering, while the Melanio leans more balanced and approachable, which is part of why it reads as the more universally appealing smoke even to people who do not usually reach for full bodied cigars.

Flor de Oliva: the value cigar that never stopped being a real cigar

This is the part Canadian smokers have been waiting for. Flor de Oliva was, in Brian's words, "the birth of Oliva," and the company's approach to it has not changed even as the rest of the portfolio has picked up trophies. "My mantra is I want an Oliva in everybody's hands who smoke cigars," Brian said. "The Floriva was, and to this day still is, a great value cigar. If I take the band off and tell you nothing about the cigar and ask you to guess how much it costs, nobody will peg it as a value cigar. The quality is there, and it's an Oliva cigar."

A few things Canadian buyers should know about what is actually landing here:

• New packaging, same blend. For this Canadian launch, Flor de Oliva is moving from the traditional bundle format into what Oliva calls the Cabinet Edition, a proper box rather than a bundle. Brian was clear that the tobacco has not changed. "The cigar hasn't changed, we just dressed it up," he said. The box format has already become one of Oliva's best sellers in other markets since it was introduced.

• Wrapper options. The original Flor de Oliva uses an Indonesian wrapper, not Habano, a point Brian corrected during our conversation. Oliva also produces a Maduro wrapper and a Connecticut wrapper version marketed internationally as the Gold. At launch, Canadian stock is centered on the natural Indonesian wrapper, with Maduro potentially following.

• Flavor profile. Expect mild to medium across the line regardless of wrapper. As Brian put it, "nobody's going to get hurt smoking a Flor de Oliva." It is an approachable, everyday cigar built for people who want quality without a heavy price tag or a heavy smoke.

• Where the tobacco comes from. Flor de Oliva draws heavily on Oliva's own Nicaraguan grown tobacco, the same agricultural operation behind the Serie V and Melanio. The difference between the lines is largely in blend composition and construction, not in a lower tier of leaf.

If you have only ever reached for the Serie V or Melanio, Flor de Oliva is worth stocking your humidor with as an everyday option, and it is a smart way to introduce a newer cigar smoker to the Oliva name without the price tag of the flagship lines. For a closer look at how the rest of the Oliva lineup compares, see our breakdown of the Serie V, Melanio, Serie O, Serie G, and Nub.

The Oliva Soccer Ball Humidor raffle

While we had Brian in for the interview, we also had one of Oliva's rarest pieces on the table: the Oliva Soccer Ball Humidor, a limited run humidor shaped like a soccer ball and loaded with 24 Serie V Melanio cigars, 12 natural and 12 Maduro, each aged three years before rolling. Brian confirmed the piece was created at the direction of Oliva's owner, Fred Vandermarliere, to mark this year's World Cup being hosted across North America. Units have shown up reselling for as much as $1,000 on eBay.

We only have a handful of cigars left before this promotion wraps, and every cigar purchase gets you a raffle ticket for a chance to win the humidor. If you have been holding off on a Flor de Oliva or Serie V purchase, this is the week to make it count. Browse our current Nicaraguan cigar selection to get started.

Rapid fire with Brian Shapiro

We closed the interview with a quick round of rapid fire questions. A few of the highlights:

• Serie V Melanio Figurado, natural or Maduro? Natural, though he says the Maduro is close behind.

• Serie V Churchill, natural or Maduro? Maduro, in a rare break from his own Serie V natural preference.

• Cutting style? Straight cut, every time. "I don't want to put much effort into cutting my cigar," he joked, and he swears he can do it in about 13 milliseconds.

• Lighter or matches? Always butane. Whatever is fastest and most reliable wins.

• How often does he make it to Canada? His last visit before this one was about three years ago. He has been to Toronto, Montreal, and Quebec, but has not yet made it out west, and told us that is next on the list.

Oliva lineup at a glance

Watch the full interview with Brian Shapiro on the Smoke Master Cigars YouTube channel, and stop into our St. Catharines or Mississauga locations to shop the new Flor de Oliva Cabinet Edition.