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Previously a house exclusive at his Leaf & Bean Strip cigar shop in Pittsburgh, "Island" Jim Robinson's Leaf series began with the now renowned Leaf by Oscar line, a unique collaboration with rising star Oscar Valladares defined by its loose tobacco leaf packaging. The first order of 1,000 cigars hit and left the shelves in one week; the following 4,000 were gone within a month. Within two years, Leaf by Oscar had swept across the country and the globe.

Since that initial success, "Island" Jim has enlisted the help of other industry leaders to create additional Leaf editions, such as Leaf by Esteban (with Esteban Disla of RoMa Craft), Leaf by James (with James Brown of Black Label Trading Co.), Leaf by Noel (with Noel Rojas of Guayacan), and Leaf by Omar (with Omar González Alemán of La Corona).