Regarding cigar culture, Miami is a city commonly reserved for the big leagues. Names like Padrón and E.P. Carillo dominate the market, having become household names over the past five decades. Despite their overarching success, smaller Miami-based brands continue to grow, steadily earning their seat amongst the giants.
Among these brands is Castellanos Cigars, owned and operated by Jesse Castellanos. Since going to market in the summer of this year, Jesse has created a way of doing business that combines cigar companies’ “old-school” family values with new-age advertising, generating incredible success since the business began.
Castellanos, a Miami native, was raised by his Cuban grandparents and recalls his grandfather, Pipo, being an avid smoker. “He was the only one that would come into the house with a lit cigar in his mouth. That was something that always stuck in my mind.” In addition to the smoking culture in his home, he also grew up in the Little Havana section of Miami, where Cuban culture flourished.
This mental image would carry him into adulthood while he was exposed to tobacco culture. As he became older, he began to learn the intricacies of the industry. “I remember getting into different wrappers and different flavors. [I remember asking] man, why is this so spicy? Is this bad? Why does it taste like this? It must be bad,” he laughably remembered.
From these humble beginnings, he soon developed a passion for smoking. He stated that as he learned more about the art of blending, he began collecting cigars. He would diligently search for rare cigars, exciting artwork, and other interesting notes.
No matter how much he learned about the industry, the rudimentary interest always came back to the relationship with his grandfather. “Every time I smoke a cigar, I think about my grandfather,” he said, describing his grandfather’s legacy. Pipo Castellanos had several business endeavors in Cuba and the United States, running a market, farm, cafeteria and opening a beauty salon for his wife. Unfortunately, Castellanos’ grandfather died by suicide unexpectedly, forcing him to reflect on his grandfather’s commitment to being a businessman.
“I wanted to create something and keep the Castellanos name alive. I also [wanted] to follow in my grandfather’s footsteps. He was a businessman; he didn’t like to work for anybody.”
When Castellanos decided to create the brand, he knew instantly that the first cigar would be a tribute to the man who continues to mean so much to him. He recalls discussing the potential idea of making a tribute cigar to Pipo with his father during their weekly cigar-smoking ritual. With only encouragement from his family, he pushed through the early obstacles of starting a business. “When you are a kid, you start something, and then you start something else, but you don’t finish. Then you start [something else], and it goes somewhere you don’t like and don’t finish. I never really had a passion behind something like that. [Maybe] sneakers. When I was a kid, I was a big sneakerhead, I bought the best sneakers and everything that was coming out. But, [cigars], it is something I like. It brings my family together, even when I was not smoking,” he said.
When he was alive, Pipo Castellanos would host gatherings centered around a caja china, roasting a pig, and bringing together all the people he loved. After the feast, he and his loved ones would all enjoy smoking a cigar in his backyard. “[Cigars] just remind me of back then, my family getting together, and obviously, my grandfather.”
As the company started to come to fruition, Jesse knew that he had to create a cigar reminiscent of the man he felt so strongly about. “It had to be a cigar that matched his character. My grandfather had [incredibly] strong character; he was very serious, he was someone that was to himself. [But], when he walked through the door, you always knew his presence… I wanted to keep it traditional to the Cuban roots, but when you open it, I [want] that band to pop… If someone is smoking the cigar, it makes its presence known.”
When the idea of starting a company was in its early stages, Jesse frequented many cigar lounges and stores in the greater Miami area. He discussed the prospects of launching a cigar company. After receiving many cautious words of advice, he established a friendship with Franco of Franco Cigars in Miami. Jesse met with several other manufacturers but could not visualize his cigar working with them. “[Franco] told me, whenever you’re ready, and you’re serious, I can give you a contact to a guy who can help you out,” he said. The “guy” was Miguel Pinto of MGE in Estelì, Nicaragua, and owner of Cigar Cigar and River City Cigars in Miami. “…Right in front of me [Franco] called [Pinto] and said, ‘Hey, I have this guy named Jesse, he’s actually right in front of me, he’s interested in making his own brand…”
Shortly after the conversation, Jesse met with Pinto at one of his shops, and they started discussing ideas on blends and the brand. To match Pipo’s character, the cigar has a medium-full body that will instill a memory of the smoking experience. He elected to use a Mexican San Andrés wrapper, Nicaraguan binders and fillers, and a box-pressed toro presentation to achieve the body. To help select tobaccos, he credits Pinto for “guiding” him in the right direction in the development process. Through Pinto, Jesse met with Nicolas Fusco of the Miami-based El Mago Cigars, also known for his tribute to his grandparents. Together, they discussed creating a cigar business and avenues of approach so Jesse could best pay tribute to his grandparents.
“At one point, he was like, man, we’ve gone through six different blends, and you aren’t happy. I said it has to be perfect. This first cigar has to be perfect,” he laughingly recalled. The meticulous process has paid off, creating a silky smooth Maduro that has kept customers returning, allowing the young company to grow exponentially since its launch, “It has the right everything, the right strength, the right flavor, the right wrapper, it’s so smooth.”
Pinto also aided Jesse in the development of the symbolic label that is seen on Pipo today. Pinto put Jesse in contact with Gianni, the head designer of Alec Bradley. When Jesse first approached Gianni, he was not taking commissions due to his busy schedule. However, after a heartfelt and honest email about the brand, Gianni called him back and professed his interest in working with him to bring the story to life.
The band is beautifully crafted with subtle gold and black lining that shapes the background; Castellanos Cigars is written in an ornate yet straightforward cursive. In the foreground is a picture of a stoic Pipo introducing himself to the world. This photo was chosen explicitly by Jesse because he used to carry the photo in his wallet after finding it in the ruins of a house fire. The band has many other features, and Gianni and Jesse worked towards solidifying the meaningful nature of the cigar. The lower band reads 1939 Limitado, paying homage to Pipo’s birthyear and the fact that the cigar is a limited edition. The circular 52 Anos alludes to his grandparents’ 52 years of marriage, followed by a Cuban coat of arms, palm trees representing Miami, a Nicaraguan coat of arms to represent the tobacco origin, and the words: para mi familia, de la familia encircled around Pipo’s photo to bring it home.
Through impenetrable drive and resilience, Jesse has forged his way through the South Florida market, selling his cigars in over twenty-five shops. With an almost inherited business sense, he meets with every shop and keeps the idea of a family-owned business alive. Through his early endeavors, he seldom met anybody who did not enjoy his cigar, only gaining him more popularity. Unlike many brands, Castellanos Cigars’ media presence directly represents his gratitude toward the shops that house his products utilizing collaborations and other methods. Through this initiative, people have started recognizing him and the band when he enters prospective shops.
When it comes to developing more cigars in the Pipo line and others, he states, “First, I’m not in a rush… Second, It’s quality over quantity… Three, I don’t have investors. I’m not rich; I have two kids, a wife, and a house, and I have a regular job as well… I’m a one-man band, starting from zero and scaling slowly… Eventually, it is going to get there, and it’s happening; it just takes time.”
Despite the enormous success thus far, Jesse admits that his biggest roadblock is time. In practice, with the family values that started his brand, he places his family first, choosing to be an active husband and father. He also notes that being an up-and-coming brand comes with difficulties. Several shops say no due to the name not being well known. This does not deter Jesse from continuing to distribute the brand widely. He expressed that he is not interested in selling online but emphasizes the importance of in-person meetings and the social aspect of cigar culture. He credits this, in addition to social media sharing, to the constant growth of the brand.
Before the end of 2024, Jesse plans to release an Ecuadorian Connecticut-wrapped cigar that will pay homage to his grandmother. He is also planning an official launch at Franco Cigars this fall. With each day passing, Jesse is expanding past the greater Miami area and is expecting to expand outside of Florida’s borders soon.
When asked what he is most proud of since starting the brand, he said the cigar represents his family well. The flavor, presentation, and smoking experience are reminiscent of his grandfather. Despite quick success, Jesse has remained humble and made his family proud, consistently hearing reaffirming statements from family members stating they knew Pipo would be proud.
Castellanos is not the first cigar brand to exist and will surely not be the last. Thanks to Jesse, this brand has affirmed itself as one of the big names of the not-so-distant future. With an unwavering passion for cigars and distinct family values, Jesse Castellanos has taken us on a journey to understand his family’s story. The story starts with young immigrants from Cuba and soars to an emerging cigar company today. Through all of the initial trials and tribulations, Jesse has remained steadfast, proving he is in it for the long haul.
All Photos provided by Jesse Castellanos, Castellanos Cigars.
Jesse with Pipo
Erick Huertas
Erick Huertas is originally from Lancaster County, Pennsylvania, and was introduced to the social aspect of cigars during his schooling in San Antonio, Texas. Around this time, he also developed a growing interest in writing and photography, using his phone camera and notepad to capture the world around him.
Erick solidified his passion for photography and adventure when he completed the Trans-American Trail in the summer of 2021 with his Land Rover Discovery 3. Since his 2021 expedition, he has been interviewed on several podcasts and has written extensively about the open road.
In 2023, Erick became involved in Grassroots motorsports by covering local Rallycross through the Northwest Rally Association, local autocross, and other events. In late 2023, he debuted as a photographer in the American Rally Association and has since covered events with Pan American Superbike and Formula E.
When not traveling, Erick can be found on Whidbey Island, Washington. You can contact Erick via email at [email protected], on Instagram at @_ebhphoto, or on his website: www.erickhuertas.smugmug.com
