Veterans Special Offer 10% OFF Your First Order! MORE INFO

Chief Of The Leaf Cigars

Maduro And
Habano Blend Cigars

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Featured Products

Check out some of our products below or click on our Shop tab to view all of our products including Cigars, Gift Sets, & Apparel.

Chief of the Leaf 2 Pack Sampler
$20.99

Chief of the Leaf 2 Pack Sampler

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Chief of the Leaf 4 Pack Sampler
$39.99

Chief of the Leaf 4 Pack Sampler

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Chief of the Leaf 10 Pack Sampler
$89.99

Chief of the Leaf 10 Pack Sampler

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Veteran Owned

Chief Of The Leaf Cigars

I am a retired Chief Master Sergeant with 35 years of dedicated service in the United States Air Force, where leadership, discipline, and commitment shaped both my career and my character. Today, I carry those same values into my passion for the cigar lifestyle as the voice behind Chief of the Leaf Cigars. As a true cigar aficionado, I appreciate not just the craftsmanship of a fine cigar, but the culture, camaraderie, and moments of reflection that come with it. For me, cigars represent more than a pastime—they embody tradition, connection, and a well-earned appreciation for life’s slower, more meaningful experiences.

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Latest Blog Post

Catch up on what's new with Chief of the Leaf! Read our latest blog posts to stay up to date on our Cigars and Brand.

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Episode 2: Maduro Vs Habano Wrapper Cigars

  • Ken Bachman
  • 12 May, 2026

Maduro vs. Habano: Understanding the Flavor Profiles of Chief of the Leaf Cigars
When cigar lovers talk about flavor, strength...

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What Our Customers Say

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I love my Chief of the Leaf T-shirt and hat, they're comfortable, well-made, and have a clean design that stands out! When I wear them to Fish Camp, my friends compliment me on how good they look. Dealing with Chief of the Leaf was so easy, and my shirt and hat arrived quickly. Can't wait to add to my collection.

Bill W.

Severna Park, MD

I just smoked my first Chief of the Leaf Habano Cigar. It's 5.5 inches with a 54 ring gauge, offering a rich blend of cedar and coco. With most of my cigars I let them sit in the humidor for about 3 months set at 68 degrees and 68 humidity for the best results. The Maduro has a smooth draw and burned evenly. As a veteran I love the fact the business is owned and operated by a fellow veteran! I would highly recommend you place an order, you won't be disappointed!

Frank L.

Millsboro, DE

Chief of the Leaf's Habano is a well-balanced, no-nonsense cigar that delivers exactly what you'd hope for from the wrapper. The construction is solid, offering a smooth draw and an even burn from start to finish. Flavor-wise, it brings a classic Habano profile earthy, slightly spicy, with just enough natural sweetness to keep things interesting. You can tell it is thoughtfully made by someone who loves the craft. A dependable choice whether you're winding down or looking for a straightforward, satisfying smoke. Two thumbs up!

James G. Warner

Robins, GA

Must Be 21 Years Old

Chief of the Leaf Cigars does not sell tobacco products to anyone under the age of 21.

Warning

WARNING: This product contains nicotine. Nicotine is an addictive chemical.

Shipping & Delivery

Mail-order sales must be shipped using services that require an adult signature (21+) upon delivery.

Customer Service

Please reach out to us through our contact form on the Contact Us page if you have any questions before purchasing.