Inside the Humidor: Meet Steve Annessi

If you’ve spent any time inside the humidor at Empire Las Olas, you’ve likely met Steve Annessi.

Every cigar in the humidor, every recommendation a member walks out with, and often the confidence a first-time smoker gains all traces back to the same place: Steve’s careful curation and guidance.

But for Steve, cigars didn’t begin as a profession. They began as a memory.

Where It all Started

“When I was a young teen, I spent a lot of time with my uncle,” Steve recalls. “He always had an El Producto or a Dutch Masters hanging out of his mouth. I just remember that aroma.”

That early association stuck with him. What began as curiosity slowly turned into a lifelong relationship with cigars, one that has now spanned nearly four decades.

His knowledge deepened significantly in 2017 while working with Drew Estate during their well-known Barn Smoker events, where he became immersed in the craftsmanship, agriculture, and blending behind premium tobacco.

“Here we are today at Empire Social,” he says with a smile.

More Than a Humidor

Steve’s role at Empire goes far beyond simply stocking humidor shelves.

“My function is multi-oriented,” he explains. “I curate the humidor, order cigars, maintain inventory monthly, and oversee lounge operations and staff when I’m physically in the building.”

But his responsibilities don’t stop with the cigars themselves. A big part of his day is spent engaging with members while they visit. “I enjoy catching up on life, checking in on how they enjoyed their last smoke, and helping make each visit feel familiar and welcoming.

His goal is simple, that every member leaves already looking forward to their next visit.

Clearing Up a Common Cigar Myth

One of the most frequent misunderstandings he encounters has to do with wrapper color.

“Many guests assume a dark cigar automatically means a strong cigar. That’s not true,” he says. “A dark wrapper, especially a Maduro, often has natural sweetness. The strength actually comes from the filler leaves inside the cigar.”

“On the other side, a light Connecticut wrapper doesn’t always mean mild in character either. It could be mild but peppery. It could be mild but creamy. There’s so much variation in blends — it’s actually pretty amazing.”

For Steve, educating guests is just as important as selling cigars.

Guiding New Smokers

Walking into a walk-in humidor for the first time can be intimidating.

Steve knows that and he has a light-hearted approach. “I ask a few simple questions,” he says. “How long have you been smoking, if at all?”

Then he explains it in a way anyone understands. “It’s like teaching someone to swim. You don’t throw someone who can’t swim into the deep end of the pool. I’m not going to give a novice a powerful full-bodied cigar that turns them off.”

Instead, he sees cigars as a progression. “It’s a journey. Start mild, but expand your palate. Don’t fall in love with just one cigar — there are too many amazing cigars out there that need to be experienced.”

What He Enjoys Most

For Steve, it isn’t about selling a cigar.

It’s about helping someone discover one they genuinely enjoy.

“I’m not just a pretty face scanning barcodes in the humidor,” he laughs. “I take a lot of pride in making a selection I believe they’re going to enjoy based on our conversation. And I always try to check back with them wherever they’re sitting in the lounge.”

Nine times out of ten, he hears the same thing:

“That was a great cigar — thanks for the recommendation.”

“That’s when I know I’ve earned their confidence,” he says. “From there, I can help members and guests develop their palate. I can suggest them moving from mild to medium, or from medium to something fuller-bodied, introducing them to new experiences they may not have chosen on their own.”

The Experience He Hopes You Leave With

Steve believes the cigar itself is only part of the experience.

“When I’m there, I try to help create an environment,” he explains. “The music, the engagement, the service — I want people to feel relaxed and taken care of with a high level of class.”

And he knows he’s succeeded when guests tell him they wished they lived here full time and want to become a member.

“For me, it’s the satisfaction of knowing they enjoyed their time and want to come back.”

steve’s Current Favorite cigar

When asked what he personally reaches for right now, his answer comes without hesitation:

“Anything Liga Privada,” he says with a smile.

Next Time You Visit

The next time you’re at Empire Las Olas, step into the humidor and introduce yourself. Whether you’ve never smoked before or have years of experience, Steve will meet you exactly where you are.

Because at Empire, cigars aren’t just about tobacco.

They’re about conversation, connection, and taking a moment to slow down.