Southern Draw Jacob’s Ladder Cigar: A Bold Journey into Flavor

When it comes to full-bodied cigars, few are as memorable as the Southern Draw Jacob’s Ladder. Launched in 2017, this bold smoke quickly established itself as a favorite among aficionados who enjoy complex, rich cigars. Southern Draw, a brand known for combining Southern tradition with faith, family, and respect, was created by Robert and Sharon Holt, a husband-and-wife team that has made a mark in the cigar world. The Jacob’s Ladder was named in honor of their son, Ethan Jacob, and also alludes to the biblical story of Jacob’s vision of a ladder connecting heaven and earth. This religious symbolism, combined with Southern Draw’s attention to craftsmanship, creates a cigar experience that is as much spiritual as it is sensory.

Every Southern Draw cigar is crafted in Estelí, Nicaragua, at AJ Fernandez’s renowned factory, one of the industry’s most respected. Fernandez’s expertise, combined with the Holts’ vision, results in unique blends that cigar lovers seek out for their depth of flavor and impeccable construction. The Jacob’s Ladder, however, is Southern Draw’s fullest-bodied offering, with strength and complexity that makes it stand out in their lineup. It’s not for the faint-hearted, but for those seeking an intense, rewarding smoke.

Construction: The Heart of Excellence

The Jacob’s Ladder is a beautifully constructed cigar that tells a story with every inch. At first glance, the dark, oily Pennsylvania Broadleaf wrapper immediately catches your attention. This Maduro wrapper, grown in the rich soils of Lancaster, PA, is almost black, giving the cigar a powerful presence before you even light it up. There’s an unmistakable sheen of oiliness, hinting at the strength and richness of the tobaccos within.

The binder is equally impressive, made from a thick Ecuadorian Maduro leaf contributing to the cigar’s overall boldness. The filler, a mix of Nicaraguan ligero tobaccos from Estelí and Jalapa, is carefully aged, offering strength and complexity in each draw. These ligero leaves are known for their strength and contribute to the Jacob’s Ladder’s full-bodied profile​.

This cigar isn’t just about raw power, though. Craftsmanship matters, and the Jacob’s Ladder shines with its tight seams, smooth surface, and well-applied dual blue and gold bands. The closed foot adds to the aesthetic while also concentrating the pre-light aromas, which include sweet molasses, earth, and a faint hint of black cherries.

Facts for New Smokers: The Basics You Need to Know

If you’re new to cigars or this specific blend, here are some quick facts:

• Length: 6 inches

• Ring Gauge: 52

• Shape: Toro

• Strength: Full-bodied

• Wrapper: Pennsylvania Broadleaf Maduro

• Binder: Ecuadorian Maduro

• Filler: Nicaraguan (Estelí and Jalapa)

• Smoking Time: 90-115 minutes

This is not a beginner cigar—Jacob’s Ladder is crafted for those who enjoy strong cigars with complex flavors. Expect an experience that will require time and attention​

Full Flavor Experience: A Journey Through the Thirds

First Third: The Peppery Prelude

Upon lighting the Jacob’s Ladder, you’re immediately greeted by a powerful blast of black pepper that coats your entire palate. This intensity, common in Nicaraguan cigars, quickly gives way to a more balanced interplay of flavors. As the pepper recedes, notes of dark chocolate, espresso, and a sweet molasses begin to emerge. The retrohale adds an extra layer of pepper but isn’t overwhelming, creating a complex and exciting start​.

Second Third: The Dark and Rich Middle

As you progress into the second third, the flavors deepen. The pepper mellows out, allowing more earthy and nutty notes to take center stage. There’s a pronounced flavor of oak, with the ligero tobaccos adding a bold, gritty character. You’ll notice hints of black coffee and leather, with an occasional pop of sweetness from black cherries. The retrohale at this point becomes smoother, introducing a touch of cinnamon, which blends beautifully with the cigar’s nuttiness​.

Final Third: The Peppery Finale

The final third brings the pepper back in full force, a sharp contrast to the smoother middle section. However, it’s not just a pepper bomb. The richness continues with flavors of cedar, leather, and toasted wood, balanced by occasional bursts of dark fruit. The cigar reaches its peak strength in this section, offering a bold yet balanced finish that will linger on your palate long after the smoke is done​.

Perfect Pairings for Jacob’s Ladder

Whiskey Pairing: Lagavulin 16-Year-Old Scotch

The peaty smoke a’s peaty smoke and rich flavor profile make it a natural partner for the Jacob’s Ladder. The deep smoky notes of Lagavulin enhance the earthy and peppery flavors of the cigar, while its slightly sweet finish mirrors the cigar’s subtle dark fruit notes.

Wine Pairing: Zinfandel

A robust Zinfandel with its spicy character and jammy fruitiness pairs perfectly with the dark, rich flavors of Jacob’s Ladder. The wine’s natural peppery kick complements the pepper notes in the cigar, while the fruitiness provides a counterbalance to the earthy and leathery tones.

Non-Alcoholic Pairing: Espresso

A strong espresso enhances the cigar’s dark chocolate and coffee notes. Its bitterness pairs well with the sweetness and earthiness of the Jacob’s Ladder, making it a perfect choice for those who prefer a non-alcoholic pairing​(

Rating Breakdown: The Full Evaluation

• Wrapper Quality: 4.5/5 – The Pennsylvania Broadleaf wrapper is beautifully dark, oily, and smooth, with minimal veins.

• Band Originality and Attractiveness: 4/5 – The dual blue and gold bands are elegant and unique, representing the religious inspiration behind the cigar.

• Feel of the Cigar: 4.5/5 – The cigar feels solid and well-packed, giving it a premium feel in the hand.

• Oiliness of the Wrapper: 4/5 – There’s a pleasing amount of oil, hinting at the rich flavors.

• Flavor Quality: 9/10 – Complex layers of pepper, earth, chocolate, and coffee deliver an engaging smoking experience.

• Aroma Quality: 9/10 – Pre-light molasses and black cherry aromas enhance the smoking ritual.

• Strength: 9/10 – Full-bodied with bold ligero tobaccos, this cigar packs a punch.

• Finish: 9/10 – Long and satisfying, with lingering notes of pepper and dark fruit.

• Burn Quality: 8.5/10 – The burn is mostly even, with minimal touch-ups required.

• Ash Quality: 9/10 – Firm and solid, the ash holds well, allowing for long stretches between ashing.

• Draw Quality: 9/10 – Smooth and consistent throughout the smoke.

• Smoke Output: 9/10 – Thick, white smoke that adds to the overall experience​(

Cigar Aficionado Score: 94/100

With an impressive score of 94, the Southern Draw Jacob’s Ladder stands out as a must-try for those who enjoy full-bodied, complex cigars. Whether you’re pairing it with a smoky Scotch, a bold Zinfandel, or a strong espresso, this cigar offers a journey into deep, dark flavors that evolve with each puff.

Enjoy the ride with Jacob’s Ladder, and as always, savor the experience.