From Betrayal to Triumph: Smoking the Montecristo No.5 with Steve Jobs in Mind

I have recently finished reading (more like listening to) the biography of Steve Jobs by Walter Isaacson. What stood out to me was how Steve Jobs was forced out of the company he had founded, Apple, by John Sculley, a CEO he’d recruited. Jobs went on to be super successful with NeXT and Pixar and was eventually brought back to Apple.

What came after was a stunning success. Apple’s market capitalisation went from USD 3 billion when he came back in 1997 to over USD 350 billion when he had to step down due to illness before his death. It has since hit peaks of nearly USD 4 trillion and brought into existence countless innovations and products loved by people around the world.

As I pick up my Montecristo No.5, which has been aging in my humidor for a few years, I think about Steve Jobs and the parallels with the book that gave Montecristo its name—Alexandre Dumas' novel The Count of Monte Cristo, which was a favourite among the cigar rollers in the Cuban factory who listened to it being read aloud during their work.

The story is about Edmond Dantès, a young sailor betrayed and imprisoned by jealous rivals, who escapes, finds a hidden fortune, and reinvents himself to get back on top. On the way to the top he drinks plenty of coffee, which was an exotic drink back in those days.

To do this Montecristo justice, I headed to my favourite coffee shop, The Espresso Lab in Dubai Design District. It has beautiful clean lines as a defining element of its aesthetic—something Steve Jobs would have appreciated. He was also known to drink loads of coffee during intense product development and creative brainstorming sessions, like our hero Edmond Dantès.

I use a V-cut on the Monte No.5 and taste the cold draw. It’s nice and sweet. I fire up the jet lighter and light it up, and get those beautiful smooth Cuban flavours I have grown to absolutely love from the Montecristo brand. Just then, the first espresso arrives. It’s an Indonesian espresso. I get some acidic, fruity flavours from it. Very nice.

I start getting some coffee and woody flavours from the Monte No.5, and it complements the Indonesian espresso nicely. So nicely I ask for my second espresso, and they duly oblige, bringing me a Guatemalan espresso and some ice-cold still water so my mouth doesn’t overheat. WHAT A COFFEE. This one tastes like melted chocolate. So, so good. Steve Jobs once said, “Stay hungry, stay foolish.”

And I’m living that right now—hungry for these flavors, foolish enough to pair a second espresso with this cigar.

The night is now going well, so well I feel sad it’s coming to an end soon. Sat outside people-watching in Dubai’s fashion capital, wearing my old ass T-shirt and shorts, is a vibe. I have drunk two espressos and I’m nearing the end of the Monte No.5. I am enjoying retrohaling this cigar as there’s no harsh flavours. This is a classic masterpiece from the Cuban Habanos S.A. stable. The notes only Cubans have are here in abundance.

Conclusion

I absolutely loved this Monte No.5. It didn’t burn very evenly and its smoke output only really increased in the second third… BUT… what a flavourful cigar.

This is why the whole world lusts over Cuban cigars (as they do Apple devices). They are treasure worth searching for, like Edmond Dantès did in the book. So, grab one (if you can find one) and pair it with some speciality coffee to make an unforgettable evening.

Nerdy Stats:

• Cuban Montecristo No.5 Cigar

• Cigar: Montecristo No.5

• Format: Petit Corona (Perla in Habanos terminology)

• Wrapper: Cuban (sourced from Vuelta Abajo, typically a light-to-medium brown Colorado Claro)

• Binder: Cuban (Vuelta Abajo, high-quality tobacco leaf)

• Filler: Cuban (long filler, tripa larga, from Vuelta Abajo’s premium fields)

• Length: 4 inches (102 mm)

• Ring Gauge: 40 (15.88 mm diameter)

• Strength: Medium

• Body: Balanced and smooth, with notes of cedar, leather, and a subtle cocoa finish

• Price Range: Mid-range for Cubans, typically AED 100 or so (USD 27+)

• Indonesian Kamala Bener Meriah 04M

• Coffee: Kamala Bener Meriah 04M

• Format: Single-origin specialty coffee (typically whole bean)

• Origin: Indonesia, Bener Meriah, Aceh, Central Sumatra

• Variety: Abyssinia, Ateng

• Process: Natural (Anaerobic Natural techniques with trial-based inoculants)

• Elevation: 1,300–1,400 meters above sea level

• Roast: Espresso Roast (medium)

• Tasting Notes: Plum, snake fruit (salak), oranges, botanicals, brown sugar

• Strength: Medium

• Body: Fruity and boozy with a complex, out-of-this-world finish

• Price Range: Specialty tier, AED 30 for a Double Espresso (USD 8)

• Guatemala Alta Verapaz Honey

• Coffee: Guatemala Alta Verapaz Honey

• Format: Single-origin specialty coffee (whole bean)

• Origin: Guatemala, Alta Verapaz (e.g., Santa Isabel Estate)

• Variety: Caturra, Bourbon (common in Alta Verapaz)

• Process: Honey (partially washed, mucilage left on during drying)

• Elevation: 1,300–1,600 meters above sea level

• Roast: Medium (versatile for filter or espresso)

• Tasting Notes: Chocolate, apple, cherry & lemongrass

• Strength: Medium

• Body: Sweet and velvety with a balanced acidity

• Price Range: Specialty tier, AED 30 for a Double Espresso (USD 8)