Drew Estate Announces the Passing of CEO Glenn Wolfson

JUNE 29, 2026 – (DORAL, FL) – It is with profound sadness that Drew Estate announces the passing of Chief Executive Officer Glenn Wolfson.

Wolfson joined Drew Estate as CEO in 2016 following a distinguished 34-year career in management consulting. During his tenure at Drew Estate, Glenn led one of the most important eras of transformation in the company’s history. Under his leadership, Drew Estate transformed its operations, dedicated itself to serving as a most trusted provider to its trade partners and consumers, and established itself as a leader in supporting and protecting the premium cigar industry. Importantly, Glenn helped guide that change while staying true to Drew Estate’s mission, core ideology, and iconic culture. ​

Today, Drew Estate is one of the largest and most admired premium cigar manufacturers in the world, renowned for its ability to disrupt, innovate, and elevate the prominence of the entire premium cigar sector. He had a genuine love for premium cigars and, above all, a profound appreciation for the people he worked with, both at Drew Estate and throughout the industry, and that profound appreciation was reciprocated.

“Glenn loved Drew Estate, its people, its brands, its culture and the broader premium cigar community,” said the Drew Estate Executive Team. “He was a transformational leader, a trusted partner and a deeply valued friend. He challenged all of us to think bigger, lead with discipline, protect what makes Drew Estate special, and build this company to last. We are heartbroken by his passing, and we are committed to honoring Glenn through the way we care for one another, serve the trade and continue carrying Drew Estate forward.”

From Sag Harbor, New York, Jonathan Drew, Founder and President of Drew Estate, writes: “In 2016, Glenn Wolfson confidently and passionately planted his roots at Drew Estate … and, like a hearty oak tree, had a disproportionately large impact on our unique ecosystem, culture, and community. ​

While Glenn’s talents in business, operations, and general commercial practices drove the company to new heights, his influence as a people person was his separate-amongst-equals … his superpower! ​ Our Drew Estate Wolfy was a natural-born leader who instinctively knew how to climb into each of our psyches, draw out our strengths, and mentor us in course-correcting our personal weaknesses. Most importantly, he accomplished this with love … really, really deep love. ​

Like the hearty oak tree, Wolfy ALWAYS gave more than he took, with a longevity-focused principle of being built to last. On many occasions, more than I can remember, I would say to him, “dude, it’s been months since you’ve taken a day off; you need to take a break.” His response was always the same … that the person needed him for the meeting, the workshop, the counseling, the reporting … the whatever. ​ If you’re reading this right now, there’s a good chance that on various occasions this person was you … from our US and Nica staff to our retailers, distributors, suppliers, and even our competitors. Glenn left nothing on the field of life. ​

A mature oak tree does far more than simply occupy space … it creates and supports a community of life, shapes entire ecosystems and influences evolution with impacts that often last for centuries. Soil, water, climate … everything … Wolfy, we will miss you profoundly.”

Drew Estate will continue to be led by its Executive Team until a new CEO is formally announced. ​

About Drew Estate

Founded in 1996 in the DUMBO neighborhood of Brooklyn, New York, Drew Estate has single-handedly defined modern-day cigar culture through a hard-hitting, authentic, bottom-up approach to lifestyle branding and culture building.

Our mission and manifesto is “The Rebirth of Cigars,” which we amplify through our uncanny authenticity, high energy and deeply loved brands produced from La Gran Fabrica Drew Estate in Estelí, Nicaragua, such as ACID, 20 Acre Farm, Deadwood, Factory Smokes, Herrera Estelí, Isla del Sol, Kentucky Fire Cured, Liga Privada, Nica Rustica, Pappy Van Winkle Barrel Fermented Cigars, Tabak Especial and Undercrown; and the celebrated Barn Smoker, Cigar Safari and Freestyle Live experiential events. ​