Not everyone enters the cigar business via the same path. Some are born into storied cigar-making families. Others work their way in by starting as cigar store owners or employees, making contacts and ingratiating themselves with industry veterans. Still, others may be enthusiasts who decide to abandon their careers to follow their passion and become a part of an industry they love and admire. And then there’s James Agopian, founder and owner of the trending boutique brand Sinistro Cigars.
As a restless and energetic kid growing up in suburban Los Angeles, Agopian was more enamored with socializing and playing video games than pursuing a career. He worked on his car, partied and hung out with friends, and took on odd jobs like delivering diamonds in the downtown LA jewelry district. When he got fed up with his bosses’ constant bickering, he decided he wanted to start his own insurance business. He was given a desk and computer in a corner of his father’s accounting offices and began successfully building his own clientele.
Not two weeks into his new gig he happened to look across the hall and see his father at his desk, where he remained daily from early in the morning to late in the evening, and an alarm went off in his head.
“I realized I didn’t want a life of sitting behind a desk,” he says. “So, I showed my dad’s assistants how to do the quotes and got a stamp made of my signature. Then I hightailed it out of there and went back to my lifestyle.”
Because the elder Agopian did tax preparation and accounting for several tobacco retailers, he was approached by a client who was opening a cigar lounge but needed a co-investor. With his son’s approval, James’s father invested the money that James had saved from writing insurance as a down payment on the cigar lounge. Within the first two months of being open, the lounge’s manager, who lived about an hour’s drive from the store, just stopped showing up. “I got a call asking, ‘Is there any way you can open the store?’ I said I don’t know anything about cigars. I’ve never smoked anything.”
But he did open the store that day, and the one day became a week, a week in which he tried various cigars, not really liking any, until he came upon a tucked-away box of Padron Anniversary. “I smoked the whole box that week. It opened up my horizons and I started enjoying cigars. I realized I’m not behind a desk, I’m constantly talking to people, not about business but about everything. This is something I can get into!”
Six months later Agopian bought the business. He operated that store, and an additional, highly successful one in San Jose, over the next 15 years. Sales were good, but a weather-related flood at his LA store, and the family-oriented direction away from smoking of the San Jose shopping center in which his store was located, caused Agopian to realize what was to come.
He says, “I saw the writing on the wall. Malls were not going to be conducive to cigar sales. I knew I wanted to get into wholesale, so I didn’t renew my lease. I took the insurance settlement from the flood and started Sinistro. The corporation was created in 2012 and in 2015 Sinistro Cigars rolled out its first three blends: Mr. Red, Mr. White and Mr. Black.
“Sinistro means ‘left’ in Latin,” Agopian explains. “I wanted to hint at something vaguely mysterious, without being so bold as to use the name Sinister. I knew we would have a red, white and black theme, but I wanted more than just a color. We had designed the logo to incorporate a gentleman—we call him The Gent—and we always referred to him as Mister, so using Mr. for the colors just seemed right.”
The next step was finding a factory that could produce his cigars while allowing him to blend creatively. Having visited the major manufacturers in the Dominican Republic, Agopian was drawn to the iconic La Aurora factory, noting, “We had a good relationship from my retail experience, and they had a ton of good, aged tobacco.” There he was mentored by Master Blender Manuel Inoa. “His blends weren’t like mine, but he allowed me to use whatever tobaccos were at my disposal.” Agopian knew he would create blends according to his own palate, and according to where he saw the market trending, but it was Inoa’s knowledge of the leaf and how to utilize it that enabled Agopian to master the art of blending.
From the start Agopian was bucking tradition. “I felt I was going in a good direction when I was told I couldn’t do something. For my first blend, Honor Among Thieves, I wanted 100 percent ligero filler. They said I couldn’t do that, but I said let’s try it. It didn’t work, so we layered some Nicaraguan Seco to improve the burn. We went with 90 percent ligero and it worked great, and now it’s one of our best-selling blends.”
Another example of Agopian’s fiercely independent streak came when he introduced his Mr. Candela, a claro-wrapped extension of the Sinistro “Mister” series. “I wanted to put a candela wrapper over the San Andrés wrapper of our Mr. Red. They said, ‘But it already has a wrapper.’ I went ahead and did it anyway, and I think it’s one of the best candelas on the market. Telling me don’t do this showed me I was going in the right direction, because I wanted to be different.”
Pandemic-related supply issues created a need for Agopian to find another importer in addition to Miami Cigars, who at the time was the U.S. importer for La Aurora. He found a new importer in El Artista, eventually using El Artista’s factory as well. The first El Artista-produced line for Sinistro was La Fabrica, which essentially consisted of overrun bundles. Agopian wanted the ratings to be based on his blends, so the next run of La Fabrica was blended by him.
Sinistro Cigars are now produced by both La Aurora and Artista Cigars, with the majority of the production coming from La Aurora. Total production numbers are currently between 300,000 and 400,000 cigars annually, and swiftly approaching half a million.
With the Sinistro Mister series having found a firm footing in the market, Agopian wanted to move the brand in a different direction. He had envisioned the concept of an aging cowboy as the logo for his next line, and in 2019 The Last Cowboy was released. Produced by La Aurora, it’s a bold blend of Connecticut broadleaf wrapper, Mexican San Andrés binder and Dominican piloto Cuban ligero filler, accentuated by a foot covering of candela wrapper leaf.
Agopian’s creative energy seems limitless, and his portfolio keeps growing, with his latest debuting at the PCA Trade Show. The Last Barbarian, another full-bodied blend, is another example of Agopian’s seemingly unbounded creativity. You just never know what will come next.
Visit sinistrocigars.com for more information on the company’s entire portfolio.
– Photography courtesy of Sinistro Cigars. Story by Larry Wagner.
This story first appeared in PCA The Magazine, Volume 3, 2023. To receive a copy of this magazine you must be a current member of PCA. Join or renew today at premiumcigars.org/membership.