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The Diamond Crown Julius Caeser Troublemaker is a 5 3/4 x 52 soft perfecto with an Ecuadorian Havana wrapper, made in the Dominican Republic by Tabacalera A. Fuente for J.C. Newman. Cigar Aficionado’s October 2025 issue rated it 91 points; we sell it as singles.
3 in stock
Description
The Diamond Crown Julius Caeser Troublemaker is a 5 3/4 x 52 soft perfecto with an Ecuadorian Havana wrapper and Dominican binder; J.C. Newman lists the filler as Caribbean and Central American, while Cigar Aficionado’s ratings list it as Dominican. Announced in October 2024, it is the only perfecto in J.C. Newman’s current Julius Caeser size list and is rolled at Tabacalera A. Fuente’s Dominican factory.
What It Tastes Like
Cigar Aficionado gave it 91 points and a medium-full rating in its October 2025 issue (Cigar Insider printed the same score that June), tasting leather, coffee, earth, a little red meat and wood ahead of a sweet, buttery close. halfwheel, reviewing it after its October 2024 debut, found cedar, black pepper and anise turning to dark chocolate, coffee and marzipan, and its reviewer counted it among the most powerful Julius Caeser smokes they could remember.
Who It’s For
- Shape hunters drawn to an odd silhouette.
- Julius Caeser regulars wanting a punchier size.
- Unhurried smokers: halfwheel’s samples averaged just over two hours.
Pros and Cons
Pros
- 91 points from Cigar Aficionado (October 2025)
- halfwheel praised its draw and frequent flavor shifts
Cons
- Cigar Aficionado’s tasters noted the burn running at a slant
- halfwheel made several burn touch-ups, and removing bands tore wrapper on two samples
About the Troublemaker
A vintage poster in the office of Rich Dolak, vice president of operations for both J.C. Newman and Arturo Fuente, supplied the shape. After Drew Newman suggested making a cigar in that shape, Dolak carved a wooden dowel by hand to match it, and that dowel was used to make the molds. It went first to 36 Diamond Crown lounges, then to retailers nationwide in May 2025.
Pairing and Storage
Both reviews found coffee, so try espresso or a medium-bodied bourbon from our cigar pairing guide. Peel the band slowly; storage tips are in our humidor basics guide.
Compare Similar Cigars
- Diamond Crown Julius Caeser Hail Caeser: the same blend in a wide 6 x 60.
- Diamond Crown Julius Caeser Pyramid: this blend at 6 1/2 x 52 with a pointed head.
- Arturo Fuente Hemingway Short Story: a 4 x 49 perfecto from the Fuente family, wrapped in Cameroon leaf.
Diamond Crown Julius Caeser Troublemaker FAQ
Is the Troublemaker stronger than the other Julius Caeser sizes?
Possibly. halfwheel’s reviewer thought so, J.C. Newman rates the core line medium, and Cigar Aficionado called this size medium-full.
Where does the Troublemaker name come from?
The shape was so difficult to roll that the cigar earned its name, according to Drew Newman. Cigar Aficionado adds that it also picked up a cheekier nickname on the factory floor.
Does the Troublemaker use the regular Julius Caeser blend?
Yes, according to halfwheel, and J.C. Newman lists the same wrapper, binder and filler origins for it. Cigar Aficionado’s ratings page lists the filler as Dominican.
Why is it spelled Caeser instead of Caesar on the Troublemaker?
J.C. Newman says an immigration officer spelled founder Julius Caeser Newman’s middle name that way in 1888, and the line keeps it. Julius Caesar Troublemaker is the same cigar.
More Newman family cigars are on our J.C. Newman Cigar Company page.
Additional information
| Packaging Type | Single |
|---|---|
| Strength | Medium |
| Origin | |
| Wrapper | Ecuadorian Havana |
| Binder | Dominican Republic |
| Filler | Dominican Republic |
| Length | 5 3/4" |
| Gauge | 52 |
