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Free Shipping on All Orders $150+

Medium Cigars

Not too light. Not too bold. Medium cigars are where balance lives, and for many, it’s the zone they keep coming back to.

Our selection of medium-bodied cigars hits that perfect middle ground: enough body to keep things interesting, but smooth enough for anytime enjoyment. These blends offer a wide range of flavor profiles, some rich and creamy, others with a subtle spice or a touch of earth, making them a reliable go-to whether you’re lighting up at the end of a long shift or gearing up for an evening with friends.

A single Deadwood Sweet Jane Corona cigar from Deadwood Tobacco, featuring a decorative and colorful band, is displayed on a white background.
An open Deadwood Tobacco box labeled "Sweet Jane" displays Deadwood Sweet Jane Corona cigars; a close-up shows a detailed band with a woman's face and floral design on one cigar.

Deadwood Sweet Jane Corona

Deadwood Tobacco Cigars
$8.99 - $189.99
$8.99 - $189.99
$8.99 - $189.99
$8.99

If you’re after a cigar that doesn’t play by the rules but still delivers a smooth, flavorful ride, Sweet Jane is calling your name. Made by Drew E...

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$8.99 - $189.99
$8.99 - $189.99
$8.99 - $189.99
$8.99

Deadwood Sweet Jane Tins

Deadwood Tobacco Cigars
$19.99 - $84.99
$19.99 - $84.99
$19.99 - $84.99
$19.99

The Deadwood Sweet Jane Tin brings premium cigar flavor into a compact, convenient cigarillo format, crafted by Drew Estate for the bold, the adven...

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$19.99 - $84.99
$19.99 - $84.99
$19.99 - $84.99
$19.99
A single Deadwood Tobacco Leather Rose Petite Corona cigar from Deadwood Tobacco Cigars, featuring a dark Brazilian Maduro wrapper and a decorative band with an illustrated figure on a white background.
An open box of Deadwood Tobacco Leather Rose Petite Corona cigars by Deadwood Tobacco Cigars shows neatly arranged Brazilian Maduro sticks; the lid displays a tattooed woman with a rose and spiderweb, while one cigar stands upright beside the box.

Deadwood Tobacco Leather Rose Petite Corona

Deadwood Tobacco Cigars
$6.49 - $149.99
$6.49 - $149.99
$6.49 - $149.99
$6.49

Big flavor in a small format, the Leather Rose Petite Corona brings Drew Estate’s spiciest Deadwood blend to a shorter, punchier smoke. Perfect whe...

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$6.49 - $149.99
$6.49 - $149.99
$6.49 - $149.99
$6.49
A single Deadwood Leather Rose Torpedo cigar by Deadwood Tobacco, dark brown with a pointed tip and an illustrated character band, rests on a white background.
An open box of Deadwood Tobacco's Deadwood Leather Rose Torpedo cigars features a stylized woman with roses on the box and band, highlighting these bold Brazilian Maduro cigars.

Deadwood Leather Rose Torpedo

Deadwood Tobacco Cigars
$20.00 - $47.99
$20.00 - $47.99
$20.00
$9.09 - $204.99
$9.09 - $204.99
$9.09

Spicy, aromatic, and unforgettable—this Flavored Maduro torpedo is the bold standout of the Deadwood lineup. Wrapped in a dark, chewy Brazilian Mad...

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$20.00 - $47.99
$20.00 - $47.99
$20.00
$9.09 - $204.99
$9.09 - $204.99
$9.09
A single Deadwood Dominicana Robusto by Deadwood Tobacco, featuring a decorative band with a woman's portrait and a silver-tipped end, this Connecticut Shade cigar is expertly crafted.
An open wooden box of Deadwood Tobacco's Deadwood Dominicana Robusto cigars, featuring a close-up of a single cigar with a decorative band and label.

Deadwood Dominicana Robusto

Deadwood Tobacco Cigars
$20.00 - $30.00
$20.00 - $30.00
$20.00
$11.99 - $102.99
$11.99 - $102.99
$11.99

The Deadwood Dominicana Robusto is a bold departure from the rest of the Deadwood lineup. Wrapped in a smooth Dominican-grown Connecticut Shade lea...

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$20.00 - $30.00
$20.00 - $30.00
$20.00
$11.99 - $102.99
$11.99 - $102.99
$11.99
A single Deadwood Tobacco Deadwood Dominicana Toro medium-bodied cigar, featuring a decorative band with an illustrated woman's face and a silver foot band, is displayed on a white background.
An open box of Deadwood Tobacco's Deadwood Dominicana Toro cigars sits beside a close-up of a medium-bodied cigar, showcasing its decorative band adorned with a woman's illustration.

Deadwood Dominicana Toro

Deadwood Tobacco Cigars
$11.99 - $102.99
$11.99 - $102.99
$11.99 - $102.99
$11.99

The Deadwood Dominicana Toro is a sweet-capped, medium-bodied cigar wrapped in silky Ecuadorian Connecticut Shade. It’s smooth, creamy, and lightly...

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$11.99 - $102.99
$11.99 - $102.99
$11.99 - $102.99
$11.99
A single Deadwood Fat Bottom Betty Robusto cigar by Deadwood Tobacco Cigars, featuring a decorative band near the top and a blue label at the foot, isolated on a white background.
An open wooden cigar box displays Deadwood Tobacco Cigars’ Deadwood Fat Bottom Betty Robusto with dark Maduro wrappers and pirate skull labels; one cigar is shown in close-up.

Deadwood Fat Bottom Betty Robusto

Deadwood Tobacco Cigars
$10.09 - $89.99
$10.09 - $89.99
$10.09 - $89.99
$10.09

Sweet, bold, and dripping with Drew Estate’s signature aromatic style, Fat Bottom Betty Robusto delivers a shorter, equally flavorful version of th...

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$10.09 - $89.99
$10.09 - $89.99
$10.09 - $89.99
$10.09
A single Deadwood Fat Bottom Betty Toro by Deadwood Tobacco Cigars, featuring a graphic band, is displayed against a white background.
A wooden box of Deadwood Fat Bottom Betty Toro cigars by Deadwood Tobacco Cigars with a lid featuring an illustrated pirate woman; one Maduro cigar is shown close-up, displaying the same signature artwork on its band.

Deadwood Fat Bottom Betty Toro

Deadwood Tobacco Cigars
$10.49 - $102.99
$10.49 - $102.99
$10.49 - $102.99
$10.49

Bold, sweet, and aromatic, Fat Bottom Betty Toro is a fan-favorite in Drew Estate’s Deadwood lineup, delivering layers of rich flavor with a smooth...

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$10.49 - $102.99
$10.49 - $102.99
$10.49 - $102.99
$10.49

This is the backbone of most humidors for a reason. At After Action Cigars, we stock proven favorites and a few unexpected standouts worth discovering. Whether you’re still dialing in your taste or already know your preferred profile, there’s a medium cigar here with your name on it. Light it. Enjoy it. Then get back after it.