Why Some Cigars Are Square

Nobody set out to invent the square cigar. In pre-embargo Cuba, makers packed rounds tightly into wooden boxes so they would survive the sea voyage without rolling around and bruising. By the time the boxes were opened, the cigars had taken on the shape of their container: pressed flat on four sides.

Then came the accidental discovery that keeps the style alive. Smokers found that the pressed cigars often drew more easily and burned more evenly than their round siblings. One tale, told by cigar writer Richard Carleton Hacker, adds that makers like Henry Clay appreciated a cigar that stayed put on a table instead of rolling off.

Modern factories produce the shape on purpose, and the deluxe method is called trunk pressing: each cigar is pressed individually between wooden slats over time, yielding sharp, deliberate corners rather than a gentle squish. It is slower, riskier work, since the wrapper can split under the pressure.

Does it change the smoke? Devotees say a press loosens the fill just enough to open the draw, and there is no arguing with how it sits in the hand. At minimum, a box press is a signal: someone at the factory took extra steps on this one.