The past 20 years have been good to Glen Case, founder and CEO of Kristoff Cigars. Starting out as a struggling, would-be cigar maker, Case can look back on his two decades of continuous growth and success with a feeling of evident satisfaction: “It’s been a blessing,” he notes. “Twenty years ago I started out in my basement, and now we’re in 50–60 countries outside the U.S., and have in-house reps all over the country.” To the inevitable question, he responds, “I don’t believe we’re boutique anymore.”
Case must have known from early on that he was meant to express himself through the creative arts. When he earned his college degree in finance, he backed that up with a degree in landscape architecture. Whether he ever planned a career in landscaping wouldn’t turn out to be the point. Rather, despite years of success in corporate finance, working for HSBC in Chicago, Case heard the call of the 1990s cigar boom. He retired from banking and joined his father-in-law in the cigar brokerage business. Unfortunately for him, but happily for cigar lovers worldwide, Case was too good at his job. As a broker in those days, if you did your job well, you soon found yourself unemployed, as you elevated the brand to the point where it could afford to hire its own in-house reps, which left you looking for the next gig. As related by Kristoff Executive Vice President Jarrid Trudeau, Case eventually got to the point where he decided, “I’m not doing this anymore. I want to make my own stuff.”
That determination was given a leg up when Case met his future mentor and manufacturing partner, Rolando Villamil, who was at the time overseeing operations for the Charles Fairmorn factory in the Dominican Republic. Villamil continued to run the factory, now known as Tabacalera Von Eicken, until his passing in 2022. It is the only factory Kristoff has ever had produce its cigars. At the time, Villamil and the Fairmorn factory were seeking someone to sell their brands in the Chicago area, and Case had a stellar reputation as a cigar broker. But Case countered their offer with one of his own: “I want you to make my cigars.” He hadn’t yet developed the blueprint for Kristoff as a brand, so Case began by selling bundles of mixed filler Dominican cigars. He felt his experience calling on retailers for the top brands in the industry had cemented strong relations with his accounts, but once he was out of the Chicago region he ran into resistance from retailers who didn’t know him, and saw no compelling reason to buy from him. He realized he was competing against established brands which had “better resources and inventories.”
That’s when Case decided to put his creativity to work, and in 2004 he established Kristoff Cigars. He wanted to create a different esthetic, and accomplished this by displaying his pig-tailed, closed-foot cigars in a bed of loose tobacco leaves, nestled inside a rustic, rough-sawed cedar box. The Kristoff line initially consisted of two blends, Original Criollo and Original Maduro. Each blend is medium-bodied, with Criollo offering hints of nuts, spices and a sweet finish, while Maduro is characterized by coffee and cocoa and a taste of dark chocolate. The Cuban-style blends, supported by the new look and a lot of legwork, started to gain recognition, as Case traveled the country trying to secure a foothold for his new brand. Trudeau recalls, “One of those trips was to Rhode Island, 15 years ago. I had read a magazine interview with Glen, and I learned a little bit about Kristoff. At a cigar dinner the next day, Glen said to the 110 people attending. ‘I’m going to do some trivia. For every question you get right, I’ll give you a cigar.’ I knew every answer because I had just read the article!”
Case was impressed and offered Trudeau a job, but soon discovered he couldn’t afford to lure him away from his lucrative executive position. The two kept in touch, while the brand grew and gained acceptance and recognition. Two years later Case made Trudeau his first in-house sales representative. Today, as VP of sales, Trudeau manages a sales force of seven in-house reps and three regional brokers, servicing over 1,000 accounts with an annual production of over one million cigars. But things weren’t always so good.
Case’s first attempt at a premium brand was called Vengeance. It was made originally by Rocky Patel. Trudeau remembers: “Prior to that, the first cigars were bundles and Cuban Selection, a sweet tipped cigar. But nobody cared about Vengeance. It had a big green V, and it was kind of ugly. We’d had some success with the bundles, then Vengeance came out, to not much success, and we realized we need to go to market with something really interesting, that people are really into. And that’s when that packaging with the Original Kristoff started.”
Since then, Kristoff has broadened the portfolio by introducing a Ligero-laced upgrade to both Criollo and Maduro, and with a succession of wrapper leaf-oriented iterations, including Cameroon, Connecticut, San Andrés, Shade Grown, Sumatra and Habano. Other brand extensions include a Signature line, showcasing the personal blends of Glen Case (GC Signature) and Jarrid Trudeau (JT Signature). Pistoff Kristoff adds a power-packed spice bomb to the company’s offerings, with Kristania offering a more wallet-friendly series to the lineup. And Vengeance is back, newly blended and presented.
Along the way, as branding and packaging evolved, Kristoff introduced three commemorative lines—Guardrail, Tres Compadres and Veinte. Each cigar features the newer, sleeker box design, accompanied by more elaborate, elegant cigar bands; and each has a story to tell. Guardrail memorializes Case’s motorcycle accident six years ago, when a guardrail saved him as his bike went into a slide. The ensuing coma and recovery were a seminal experience for Case. Trudeau explains how the cigar came about: “We had gotten this special tobacco from Zimbabwe, and Glen really liked it. We were planning what we wanted to do with it and Guardrail is what came out of that.” Fortunately, Case had a full recovery, and Guardrail is a tribute to that experience. The rare Zimbabwean leaf is paired with Dominican filler and binder, under a Brazil Maduro wrapper, resulting in a balanced, medium-full smoke.
Tres Compadres is a testimonial to friendship. It celebrates the bond between Case, lifelong friend Chuck Finch, and Rolando Villamil, who served not only as a mentor to Case, but also as a close friend to both of them. Case relates the backstory for the commemorative issue: “Three years ago last October Chuck passed away unexpectedly. We had been friends for 40 years. Four months later Rolando passed away. It’s a tribute cigar to them, and to both of their palates. It’s a Nicaraguan puro, but not with big pepper and spice. It’s a sweet, creamy cigar with some light-hearted spice.”
The third entry in the new-format series is the culmination of Case’s 20 years as a cigar blender and brand owner, aptly named Veinte. Commemorating two decades of achievement presented Case with quite a challenge. “It was probably the toughest cigar to blend,” he recalls. “In my mind it had to be perfect. I don’t know how many different blends we tried, how many different people smoked it, people whose palates and feedback I trust. It’s been doing incredibly well, and it’s in full production, so it’ll be around forever.” Veinte is billed as medium-full-bodied, composed of a Brazilian wrapper over an Indonesian binder, and Nicaraguan and Pennsylvanian fillers. The cigar debuted at the 2024 PCA Trade Show to an enthusiastic reception by those in attendance.
In addition to serving as VP of sales for Kristoff, Trudeau has been a member of the PCA Board of Directors for the last three years. Although he’s always busy with his responsibilities at work, Trudeau says he felt this was something he needed do. “This industry has given a lot to me and my family, and I wanted an opportunity to give back, to do something for the industry,” he relates. “As a manufacturer, our representation on the board is important as well.”
For his part, Glen Case is focused on continued growth for the brand, both nationally and internationally. “We’ve been blessed with growth year over year, record year after record year. Jarrid, Chief Operating Officer Ward Hall and I have been together for 11 years now, we’ve had our reps for nine or 10 years—a fantastic team.” He goes on to project what lies ahead for his burgeoning brand: “For this year’s show we’re doing a PCA Exclusive. We’ll continue to come out with new blends.”
Case and Trudeau hasten to add some exciting news for the brand coming up at PCA 2025.
The Trade Show and Convention in New Orleans will be the venue for the release of the all-new Kristoff rebranding, featuring updated, 20-count packaging for the entire line. Modeled after the sleek, new style for the Veinte line, Trudeau says: “That is the design language we’re going to use going forward.” The two men refer to the newer design as “traditional elegance.” The redesign has been in the works for the last year and a half, and Case adds, “The goal is to present at the show in April all our new packaging, in a classic contemporary style, and to bring continuity throughout the brand.”
With a revamped lineup featuring a sophisticated, contemporary look, and a vision of continuous expansion and growth, one can expect to see Kristoff cigars on the shelves of premium tobacconists for generations to come.
For more information visit kristoff.com.
– Photos courtesy of Kristoff Cigars. Story by Larry Wagner.
This story first appeared in PCA The Magazine, Vol. 1, 2025. To receive a copy of this magazine you must be a current member of PCA. Join or renew today at premiumcigars.org/membership.