In 1896, a Ukrainian immigrant named Samuel Paley opened established a cigar shop in Chicago and formed the Congress Cigar Company which began manufacturing and selling a cigar brand by the name of La Palina, loosely translated as "The Female Paley".

What is now a famous brand and logo was first created when Sam's wife Goldie Drell Palay, dressed in Spanish costume posed for the La Palina cigar box label, and this image remains in use to this day. 

In 2010, though, William "Bill" Paley Jr. re-acquired the rights to his grandfathers brand and named the company La Palina Cigars. The first modern La Palinas were produced in the Bahamas in limited quantities, and the least expensive was $18. Despite the high price tag, the brand gained a loyal following.

Today La Palina cigars are manufacturered in the Dominican Republic and Honduras.