Skip to content
  • Cigars
  • Pipe Tobacco
  • Merch & Accessories
  • Events
  • Visit Us In Person
  • Sign Up for Email Notifications
Login
  • Twitter
  • Instagram
Search
Chesterton & Co. Cigars Online
  • CigarsCigars
  • Pipe TobaccoPipe Tobacco
  • Merch & AccessoriesMerch & Accessories
  • EventsEvents
  • Visit Us In PersonVisit Us In Person
  • Sign Up for Email NotificationsSign Up for Email Notifications
Search

Confirm your age

Are you 21 years old or older?

No, I’m not
Home Search Shop 0 Cart Account
The Prince of Paradox Barberpole Cigar
The Prince of Paradox Barberpole Cigar
The Prince of Paradox Barberpole Cigar
The Prince of Paradox Barberpole Cigar
The Prince of Paradox Barberpole Cigar

The Prince of Paradox Barberpole Cigar

$55.99

The Prince of Paradox Barberpole

"The paradox of courage is that a man must be a little careless of his life even in order to keep it." - G.K. Chesterton

G.K. Chesterton, the legendary English writer and philosopher, was affectionately known as the "Prince of Paradox." He famously used paradoxes—ideas that seem contradictory on the surface but reveal a profound underlying truth—to turn the world upside down so his readers could finally see it right-side up.

Crafted in his honor, The Prince of Paradox is a cigar that defies expectations and challenges the palate. It is a brilliant contradiction, woven together to deliver an unforgettable smoking experience that commands your attention before inviting you to sit back and reflect.

The Anatomy of a Paradox

Like two opposing thoughts seamlessly braided to make a singular, brilliant point, this 6x54 masterpiece features a visually striking barberpole wrapper. The dark, rich, and decadent Maduro leaf intertwines flawlessly with an earthy, vibrant Sumatra wrapper. The result is a cigar that looks as complex as the smoke it delivers.

The Experience

The true paradox reveals itself the moment you apply the flame.

The Introduction: You are immediately greeted by an unapologetically bold, full-bodied blast of rich spice and deep pepper. It is a powerhouse start designed to grab your attention immediately—much like the sharp, witty opening of a Chesterton essay.

The Revelation: Just as you brace yourself for a heavy, relentless smoke, the paradox unfolds. About one-third of the way through, the aggressive spice suddenly yields. The profile mellows dramatically, transitioning into a remarkably smooth, balanced, and contemplative smoke. The dual wrappers harmonize to produce rich, creamy notes of dark cocoa, roasted nuts, and sweet cedar that carry you all the way to the nub.

It starts with a roar and finishes with a whisper. It is bold, yet mellow. It is the Prince of Paradox.

Cigar Specifications

Comes in 4 pack and 8 pack bundles

  • Size: 6 x 54 (Toro Extra)

  • Wrapper: Dual-Wrapper Barberpole (Maduro & Sumatra)

  • Binder: Masterfully Selected Premium Leaf

  • Filler: Aged Long-Filler Tobaccos

  • Strength: A true contradiction (Starts Full/Spicy, transitions to Medium/Smooth)

  • Tasting Notes: Initial bursts of bold spice and black pepper, mellowing gracefully into dark chocolate, rich earth, sweet cedar, and a creamy, lingering finish.

bundle size
bundle size: 4 pack bundle

notice: email required at checkout for tobacco purchases

 

Share:

  • Share on Facebook
  • Tweet on Twitter
  • Pin on Pinterest
  • Share by Email
Share
Share
  • Facebook Share on Facebook
  • Twitter Tweet on Twitter
  • Pinterest Pin on Pinterest
  • E-mail Share by Email
Need help?

Pairs well with

The Prince of Paradox Barberpole Cigar

The Prince of Paradox Barberpole Cigar

4 pack bundle
$55.99
© 2026 Chesterton & Co. Cigars Online Built by Honeycomb Media. Powered by Shopify
  • Refund policy
  • Privacy policy
  • Terms of service
  • Shipping policy
  • American Express
  • Discover
  • Mastercard
  • Visa

Chesterton & Co Cigars is co-owned by Rob Praetzel & Zeph Swope, who founded and opened the business in 2022.

  • Choosing a selection results in a full page refresh.
  • Opens in a new window.