Craig Reynolds, the leader of the Cigars International—the world’s largest cigar retailer—will be retiring in May 2020.

That is when his contract ends, though Reynolds told halfwheel there is a chance that he might stay with the company in a consulting role, though nothing has been finalized.

Reynolds joined the company in February 2009 as an executive vice-president, he was promoted to president in 2011 and in 2016, he was promoted to evp of global handmade cigar businesses for Scandinavian Tobacco Group (STG), which owns Cigars International. Through that role, Reynolds was both the head of Cigars International as well as being the direct boss of the head of General Cigar Co.

Cigars International is the world’s largest retailer. It includes the eponymous Cigars International brand—which operates an online store, a catalog and four brick-and-mortar stores—as well as,, and Thompson Cigar Co.

All of the brands outside of have physical catalogs, Thompson still operates a physical storefront in Tampa and Cigars International hosts the largest cigar event in the world, CIGARFest.

Reynolds’s tenure saw the acquisition of in 2013 and Thompson Cigar Co. last year. The company has also announced the first Cigars International retail stores outside of Pennsylvania: a store in Texas opened last year and two stores are planned for the Tampa area. Reynolds told halfwheel that his contract expires in May, so his retirement isn’t based on completing any major projects like the opening of the Florida store.

In 2007—before Reynolds joined—Cigars International was sold to Swedish Match and in 2009 it was merged with the company that owned CAO to create the STG we know today. Five years later, it was announced that STG would be going public.

While the IPO was relatively successful, being a public company meant an increased spotlight on any major issues. The most notable one came in 2017 when Cigars International upgraded some of its backend software. That update led to a number of errors including the loss of order records. Customers placed orders and CI couldn’t properly see that they had been placed. To make matters worse, the upgrade included its customer service platform, meaning that many customers complained but CI couldn’t see those complaints either.

The mistake was large enough that STG was forced to downgrade its stock forecasts and Reynolds made a rare public statement, in a video nonetheless.

While 2017 had very public missteps, most of Reynolds’ tenure has seen Cigars International increase its power and presence in the industry. The company’s share of the overall cigar market has increased dramatically in the last decade and its brick-and-mortar strategy has been far more successful than its largest competitor, JR Cigar. The acquisition of Thompson meant that STG now controlled two of the five largest retailers under one roof.

Despite having one of the most powerful jobs in the cigar industry, Reynolds has kept a low profile, so much so that few mentioned his absence at the recent IPCPR Convention & Trade Show. His decade-plus tenure at CI has also produced much more stable leadership than that of CI’s largest competitor. For context, JR Cigar is on its third ceo since the start of 2017.

A replacement for Reynolds is expected to be named in Q4.

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Charlie Minato

I am an editor and co-founder of Media, LLC. I previously co-founded and published TheCigarFeed, one of the two predecessors of halfwheel. I have written about the cigar industry for more than a decade, covering everything from product launches to regulation to M&A. In addition, I handle a lot of the behind-the-scenes stuff here at halfwheel. I enjoy playing tennis, watching boxing, falling asleep to the Le Mans 24, wearing sweatshirts year-round and eating gyros. echte liebe.