We Gave AI $500 To Shop For Cigars. This Is What It Bought.
This was probably not the smartest idea I have ever had at Cigar Press….giving AI $500 and telling it to go buy us some cigars. Then again, we did give it a few rules, not full access to our bank accounts, and wanted to see what happened.
Total Spend: $496.45 (see, we already saved $3.55).
It only made sense. Humanity has reached the point where we no longer just ask artificial intelligence to make funny pictures, videos of Tom Cruise fighting on a rooftop, summarize emails, spellcheck headlines, and pretend to understand our spreadsheets.
Nope. Now we handed AI $500 and let it loose on a cigar website like a digital sommelier with no pulse, no drama, and suspiciously strong opinions about wrapper leaf.
We told it not to seek out ‘expensive singles’ unless it felt strongly (we didn’t want to burn through our budget too fast). We also asked it to pick a brick-and-mortar with a substantial online inventory. We told it to stay value-conscious, avoid junk, buy only quality cigars, and act like somebody who actually knows the difference between a bargain and a mistake. The result is a surprisingly solid cart.
This is either impressive help or the next quiet step toward a full machine takeover. I’m thinking probably both.
The $500 AI Cigar Cart…
| Cigar | Vitola | Pack | Price | Qty | Subtotal | Running Total |
|---|---|---|---|---|---|---|
| Padron 2000 Natural | 5 x 50 | 5-pack | $43.50 | 1 | $43.50 | $43.50 |
| Padron 3000 Maduro | 5.5 x 52 | 5-pack | $48.00 | 1 | $48.00 | $91.50 |
| My Father Le Bijou 1922 Grand Robusto | 5 5/8 x 55 | 5-pack | $57.50 | 1 | $57.50 | $149.00 |
| La Flor Dominicana Air Bender Maestro | 5.5 x 52 | 5-pack | $48.50 | 1 | $48.50 | $197.50 |
| Crowned Heads Four Kicks Capa Especial Corona Gorda | 5 5/8 x 46 | 5-pack | $43.50 | 1 | $43.50 | $241.00 |
| Drew Estate Undercrown Maduro Corona Viva | 5 5/8 x 46 | 5-pack | $46.00 | 1 | $46.00 | $287.00 |
| Espinosa Laranja Reserva Robusto Extra | 5.5 x 54 | 5-pack | $67.50 | 1 | $67.50 | $354.50 |
| Montecristo Nicaragua Toro | 6 x 54 | 5-pack | $80.00 | 1 | $80.00 | $434.50 |
| Perdomo 20th Anniversary Connecticut Torpedo | 6.5 x 54 | 5-pack | $61.95 | 1 | $61.95 | $496.45 |
Why These Cigars Made the Cut (well, according to AI)…
Padron 2000 Natural
This is the kind of cigar that ends arguments quickly. It has the Padron name, proven consistency, and a reputation for punching above its price point. Expect a balanced profile with cedar, earth, coffee, and enough richness to remind you why people keep buying these by habit. AI picked it because value matters, and pretending otherwise is how people end up overpaying for packaging.
Smoke Inn product page | Outside review
Padron 3000 Maduro
Same family, darker suit. The Maduro version adds cocoa, espresso, and a little more grit without losing the series’ famous reliability. This made the list because if you are doing a value-conscious premium order and skipping Padrón entirely, you are either trying too hard or shopping emotionally.
My Father Le Bijou 1922 Grand Robusto
This is where the cart gets serious. Le Bijou has the kind of pedigree that makes cigar nerds speak in reverent tones and overexplain pepper. Rich, spicy, and layered, it brings roasted pepper, cocoa, leather, and cedar to the mix. AI grabbed this because it wanted one cigar that clearly says, “I know what I’m doing,” even if it is still technically a machine.
Smoke Inn search | Outside review
La Flor Dominicana Air Bender Maestro
Air Bender is not subtle, and that is part of the charm. It has a reputation for strength, depth, and mid-90s-level praise from reviewers. You get earth, espresso, chocolate, spice, and that unmistakable LFD attitude. AI picked it because every good lineup needs at least one cigar that feels like it could win a fight in a parking lot.
Smoke Inn search | Outside review
Crowned Heads Four Kicks Capa Especial Corona Gorda
This is the curveball. Sumatra wrapper, nuanced profile, and more flavor detail than the usual “pepper, wood, done” routine. Cinnamon, brown sugar, candied nuts, and suede leather make this one stand out. AI included it because variety matters, and because a cart full of nothing but dark broadleaf hammers starts to look less like taste and more like a personality disorder.
Drew Estate Undercrown Maduro Corona Viva
Undercrown Maduro is one of the safer smart buys in the premium world. It gives you thick smoke, dark chocolate, espresso, pepper, oak, and enough richness to scratch the Liga-style itch without setting your wallet on fire. AI picked this because it understands one of the most important principles in cigar shopping, which is this: close enough can be very profitable.
Smoke Inn search | Outside review
Espinosa Laranja Reserva
Laranja Reserva brings a complex mix of cedar, honey, and spice to create a cigar that works any time of day. AI took it because quality still matters when you are being value conscious. Cheap and smart are not the same thing, despite what the internet keeps trying to prove.
Montecristo Nicaragua Toro
This is the luxury pick. AJ Fernandez craftsmanship, Montecristo branding, strong construction marks, and a profile that leans into pepper, sweetness, and body. It gives the cart a high-end anchor without turning the whole thing into an exercise in financial irresponsibility. AI picked it because every respectable order deserves at least one cigar that says, “Yes, I have standards.”
Smoke Inn search | Outside review
Perdomo 20th Anniversary Connecticut Torpedo
This is the value hero and the palate balancer. It keeps the cart from becoming a one-note parade of full-bodied aggression. Creamy, toasty, peppery, and polished, it gives you a Connecticut that still has structure. AI picked it because even the machines understand you cannot smoke like a maniac every day unless you enjoy turning your tongue into roofing material.
Smoke Inn search | Outside review
Why This Mix Works
This order is balanced the way a good humidor should be. I mean, it’s no Essential 30, but I will give it a pass. There are dependable daily drivers, richer weekend cigars, a premium flex, and enough wrapper and strength variation to keep the experience interesting. Nicaragua, Honduras, Dominican Republic, Connecticut, Maduro, Sumatra, Habano, stronger blends, smoother blends, all covered without wasting money on filler picks that only exist to pad a shopping cart and disappoint you later.
Best Value Pick
Perdomo 20th Anniversary Connecticut Torpedo
Smooth, reliable, flavorful, and reasonably priced. This is the cigar in the cart that quietly does everything right while flashier cigars demand attention like insecure influencers.
Most Interesting Pick
Crowned Heads Four Kicks Capa Especial
This one brings a different flavor lane to the order and keeps the cart from feeling lazy. Cinnamon, brown sugar, nuttiness, and leather give it more personality than the average “strong cigar for strong men” routine.
Luxury Pick
Montecristo Nicaragua Toro
The priciest pick here, but not a vanity purchase. It earns its place with construction, pedigree, and a profile that feels upscale without becoming absurd.
What AI Skipped (In This Case) and Why
We dug into the code to understand AI’s thought process. Although we did not make a ‘runner-up’ list, these almost made the cart. Here is why they didn’t (in this case).
- Liga Privada No. 9 because it overlaps too much with Undercrown Maduro while costing more.
- Davidoff Late Hour because the quality is real, but the pricing in this case was less “value-conscious.”
- Lower-end budget fillers because buying more cigars is not the same as buying better cigars, no matter how good the math looks.
Does AI Actually Have Good Taste in Cigars?
So there it is. We gave artificial intelligence a budget and enough freedom to do something either impressive or mildly concerning.
Instead of ordering nonsense, it built a cart that actually makes sense, stayed under budget, and somehow avoided the usual internet trap of confusing hype with quality.
Today, it picked a smart lineup from Smoke Inn. Tomorrow, it learns how to rotate our humidor, judge my cutter choice, and quietly replace me in the group chat with somebody who retrohales with gusto.
If the machines are coming, at least they have decent taste in cigars.
About the Author: Fred Rewey
