Just who is Jim Robinson?

To many, he’s “Island Jim,” a name given to him by Eddie Ortega and fitting for his love of tropical shirts and his former residence in Key West, Fla. He wasn’t always “Island Jim” though; in a former life he worked for Marriott and lived the clean-shaven, suit-and-tie world of hotels and hospitality, in particular spending weeks at a time on the road and properties around the country doing training and quality control. But he gave that life up to return to Pittsburgh, which is where “Island Jim” really came to life.

He’s a retailer, known for the Leaf & Bean Strip in Pittsburgh, Pa. He’s also a brand owner, having created the Leaf by Oscar as a house cigar that has since found its way into nearly 1,000 retail shops, as well as the Island Jim No. 2. If you don’t know him personally, you might know him as one of Ortega’s Wild Bunch, having appeared on the series’ third installment, a cigar named for his often-uttered phrase, “wahoo,” which is used for everything from greetings to celebratory exclamations to a general utterance to signify a state of well-being. It’s an association to him that’s second only to his signature yellow sunglasses.

As those who have visited his shop will tell you, he’s amassed a collection of all sorts of things, though it doesn’t seem right to call him a collector of things. But beyond that, he’s an explorer, readily admitting to being in love with the small towns and villages of Honduras and spending as much time as he can both on and off the beaten path when in the country visiting Oscar Valladares’ factory in Danlí to check on the production of his cigars or work on a new creation, a factory which he is largely responsible for helping to make possible by way of the Leaf by Oscar and his other projects, and which has given not only Valladares a chance to show what he can do, but many others who work in the factory.

He has a certain love of life that becomes more and more apparent as you talk to him, spend time with him, and see that wahoo isn’t just a catchphrase, but rather how he sees the world. I had the fortune to spend several days with him in Honduras, and he brings a feeling of connectedness to the world that you just don’t get from everyone you meet. He eschews his own publicity, yet leaves an unmistakable impression on seemingly everyone he meets, and not just because of his signature look. Whether it’s browsing artisans’ shops, having dinner at a roadside tamale stand under a sky full of stars, traversing the Honduran countryside on dirt roads in the back of a pickup truck or buying groceries for a village elder, candy for local kids and some treats for a dog, his generosity and connection to those around him readily shows through. — Patrick Lagreid.

%22Island Jim%22 Robinson

This portrait was taken in the José Martí airport in Havana, Cuba, at the airport’s lounge during a 10-hour delay. It was shot using a Canon 5D Mark III and a 50mm f/1.2 lens set at f/5.6. The shutter speed was 1/40 second at ISO 3200. The only source of light was flame coming off of the foot of the cigar, and I shot through a frosted glass wall that was covered in the word smoke in different languages, which designated the smoking lounge. The photograph was color corrected in Adobe Lightroom and adjusted for color, contrast and sharpness using custom actions in Photoshop CC.

Brooks Whittington

I have been smoking cigars for over eight years. A documentary wedding photographer by trade, I spent seven years as a photojournalist for the Dallas Morning News and the Fort Worth Star Telegram. I started the cigar blog SmokingStogie in 2008 after realizing that there was a need for a cigar blog with better photographs and more in-depth information about each release. SmokingStogie quickly became one of the more influential cigar blogs on the internet, known for reviewing preproduction, prerelease, rare, extremely hard-to-find and expensive cigars. I am a co-founder of halfwheel and now serve as an editor for halfwheel.