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Cigar Industry July 1, 2026

Drew Estate Announces the Passing of CEO Glenn Wolfson

It is with profound sadness that Drew Estate announces the passing of Chief Executive Officer Glenn Wolfson.

Text: Press Release
Drew Estate Announces the Passing of CEO 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 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.

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 individual psyches and drive our strengths while mentoring us on how to course-correct 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.

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