From celebrating championship moments with cigars to having their names behind the brands, athletes have taken interesting turns in business. Some even have their own cigar brands, blended from their personal favorites. Former Atlanta Hawks star Dominique Wilkins is one of the notable names. Another household name in the NBA industry to have launched a new lineup is Dennis Rodman. “The Worm” has been a big enthusiast of cigars, and he channeled that passion into his business. He also has experience from the past. Very few people know that he had even bigger plans for his new lineup and wanted to collaborate with an NFL great.

The rebound king won three championship titles with the Chicago Bulls. The 63-year-old who is famous for his odd antics, was known to the league for his elite defense and rebounding skills. He played an instrumental piece alongside Michael Jordan and Scottie Pippen. Both Rodman and Jordan share the same love for cigars. In the present, he had teamed up with Dreamers Cigars in 2024 and launched a new line of cigars. 

Rodman’s love for cigars isn’t just a hobby—it’s a passion he’s been chasing for years. He once launched the WB Brand Cigar line, a small venture named after his “Worm” nickname. It didn’t take off as hoped, mostly because of limited distribution, but it showed Dennis was serious about breaking into the cigar world. That experience gave him the know-how to dream bigger, like teaming up with a star like Chad Ochocinco—though that collaboration didn’t happen—to make a splash in the growing cigar market.

The founder, Adam Guard, recently sat down for an interview with the Spartans Leadership Podcast. Speaking of the venture, Rodman’s new partner and founder of Dreamers Cigars shared a lot of insights he gained while working closely with Rodman. One of the most surprising details he shared was Rodman’s interest in working with NFL legend Chad Ochocinco’s brand Eighty5 which was launched in 2016.

They were initially a social media brand and had connections with Ochocinco. He was then offered the chance to team up with Rodman. Upon landing the opportunity, he took the challenge and it’s safe to say that they are good at it.

“We started doing some consulting for them (Ochocinco) and then Dennis wanted to do a cigar with Chad and they just couldn’t handle it. The bandwidth wasn’t enough And they said ‘Do you want to do Dennis’s cigar?’ And I said ‘Absolutely I do.’” he said. And this is how the collaboration began. 

He added, “But you talk about entrepreneurship I had never created a cigar before at all And I you know it’s one of those things where you run through the door right it’s like oh well that’s not what we.” (But) I’m going to figure it out right and that’s the way it went. We had the call started talking to Dennis’s agent and we just ran with it and we created if I can say so one of the best Connecticut cigars I’ve ever smoked.”

While Rodman wanted to team up with Chad, the NFL star is quite the expert himself. This isn’t Rodman’s first venture in the $14 billion (as per Statista) valued Cigar industry, he also had earlier launched WB Brand Cigar line. Guard also expressed gratitude to Rodman for guiding him. The founder also discussed the challenges they faced while working on the project for Rodman.

Adam Guard faced daunting challenge in collaboration with Dennis Rodman

To work on the collection and cigars, Guard, who was new to the industry, faced a challenge in communication. He wanted to work in Nicaragua, which is one of the highlights of the lineup. However, when he spoke to the factories, they only spoke Spanish. When the host asked about what were the initial steps, Guard revealed it to be finding the right connection.

 “I cold called factories. I don’t speak Spanish so some of it was tricky but you know you say is there anyone else around that can translate for us and you keep digging until you find the right one right we kept exploring,” he shared. This wasn’t the only challenge. However, he ultimately found the right factory. He worked closely with the factory that produced the cigars for the lineup to craft and curate a new collection. 

Nicknamed Ring of Honor Cigar, this was a special edition release, limited to 250 boxes of 20 cigars each. As per HalfWheel, these were crafted at the SCT factory in Estelí, Nicaragua. Each box was priced at $397. This edition was to pay homage to the legend for being named in the Chicago Bulls Ring of Honor alongside Jordan and Pippen. From finding translators to ultimately creating new cigars for Rodman, the brand has come a long way.