By Timothy S. Donahue
Top Takeaways:
- Industry leader remembered: Drew Estate CEO Glenn Wolfson has died after a brief illness, having led the premium cigar company since 2016.
- Eight years of leadership: Wolfson joined Drew Estate after Swisher acquired the company and helped guide its growth and integration.
- Succession underway: Wolfson had been preparing for retirement and helping oversee the search for his successor before his death.
Drew Estate Chief Executive Officer Glenn Wolfson has died after a brief illness, ending an eight-year tenure during which he helped lead one of the premium cigar industry’s largest manufacturers through a period of growth, organizational transformation and integration under its parent company, Swisher.
The company announced Wolfson’s passing on Monday. In May, Wolfson told colleagues he had been diagnosed with pancreatic cancer and had begun treatment. He continued working while overseeing the search for his successor as he prepared for retirement.
Wolfson joined Drew Estate as chief executive officer in July 2016, shortly after Swisher International acquired the company. Before entering the premium cigar industry, he spent most of his career as a management consultant and corporate executive, serving in leadership and advisory roles at firms including Booz Allen, Korn Ferry, Sibson Consulting, and Twinlab Consolidation Corp. He also earned an MBA from Northwestern University’s Kellogg School of Management.
Under Wolfson’s leadership, Drew Estate expanded its standing as one of the world’s leading premium cigar manufacturers while preserving the entrepreneurial culture established by founder Jonathan Drew.
At the announcement of Wolfson’s death, Jonathan Drew, the company’s president, highlighted his leadership style and commitment to employees and industry partners.
“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,” said Jonathan Drew, the company’s president, in a press release. “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 U.S. and Nica staff to our retailers, distributors, suppliers, and even our competitors. Glenn left nothing on the field of life.”
During his tenure, Wolfson helped oversee Drew Estate’s continued expansion in the premium cigar market and strengthen the company’s operational capabilities following its acquisition by Swisher. The company remained one of the industry’s largest premium cigar manufacturers, with production centered in Nicaragua and products distributed worldwide.
Drew Estate said that Wolfson’s responsibilities will be shared among members of the company’s executive leadership team as the succession process continues. The company did not announce funeral arrangements.





