Cigar Lounge – Leaf and Bean Strip – Pittsburgh, PA

As I continued the Stogie Press cigar lounge tour of the northeast, I met up with my associate Mike Bruce in Pittsburgh, PA and we headed off to visit the Leaf and Bean cigar shop in the Strip District, downtown Pittsburgh. Leaf and Bean is owned and operated by Island Jim Robinson, the iconic purveyor of the famed Leaf by Oscar and Island Jim line of cigars.  Jim was out of town on business the day we visited by his main lady, Melody Troutman met us in the morning and gave us the grand tour of not only Leaf and Bean but also the new Leaf and Bean Private lounge, just down the road in Lawrenceville, PA. Wahoo, two tours in one!

A little Background on Island Jim

Most who know Island Jim Robinson know him as the iconic face behind the Leaf by Oscar and Island Jim cigar brands, but he did not always have the look he has now. Jim actually came out of the corporate world where he worked for the Marriott Corporation managing the company’s hotel properties for over 17 years. His last assignment was managing the Casa Marina Resort in Key West, FL.

After leaving Marriott, Jim opened a restaurant but shortly realized he did not like the restaurant business. Being a patron of the original Leaf and Bean cigar shop, he made a royalty deal with owner Gregg Threlkeld to open up the Leaf and Bean Strip. With the help of Greg,  the new strip location started to grow slowly. Beginning with just a small assortment of cigars, Jim would buy some, never using credit or terms, and when he made a profit, he would buy and add more.  The business started to flourish in the downtown strip location. It was a comfortable hip place to hang out and enjoy coffee and cigars.

We all know how the story progressed when Jim took a trip to Honduras and met with his long time friend Oscar Valladares who was looking to do something new in the business. Oscar wanted to branch out on his own and start his own factory. Jim jumped at the thought and requested that one of the first cigars be for him. They worked together and eventually created the Leaf by Oscar which was brought in as a house cigar for Leaf and Bean Strip.

The project was a success but there was a bit more to the story as Jim notes on the Leaf By Oscar website:

When Oscar, after months of working together, asked about my first order, I told him “5,000 for the year.” At the same time, I thought, Wow, that’s a big order. How am I possibly going to sell that many of one cigar in a year?


Oscar looked at me and I could practically see his thought, All this work for only 5,000 cigars?

With the first batch done, all 5,000 cigars made, I realized I had no idea how to get them to Pittsburgh.

I happened to have a group of ten in Honduras at the time. Each person could legally bring back 100 cigars. That made 1,000 cigars for my retail shop. That will last me a while, I figured. And give me enough time to get the other 4,000 to the US. I was pretty pleased.

One week after putting the 1,000 Leaf by Oscar cigars on my shop shelf, they were gone. All of them. Sold. In one week. I needed a crash course in importing. I needed a broker.

The remaining 4,000 cigars soon made their way to the Leaf and Bean and within one month, they were gone. All of them. Sold. In a month.

The house brand concept lasted only several months as calls started coming in from retailers who wanted to carry the line. Now the “Leaf By” products which include the Leaf By Oscar, Leaf by Estaban, Leaf by James, and Leaf by Omar have expanded to 49 states in the US. The only state that does not carry them is Alaska. The factory that started with just 3 rollers has expanded to over 200  and distribution is now in Canada, Germany, Copenhagen, Amsterdam, and the Caribbean Islands.

Leaf and Bean Coffee and Cigar Shop

The Leaf and Bean Coffee and Cigar Shop located at 2200 Penn Avenue, Pittsburgh, is as iconic as the man who owns it. The shop was actually a car garage prior to Jim opening the shop which is in the center of the what is known as the “Strip District”, a narrow one-half square mile area of land that runs from 11th to 33rd street just south of the Allegheny River. The area was originally a warehouse district that was the home to a number of mills and factories during the 19th century. As more highways and byways were developed the need for shipping reduced and the area began to transform in the 20th century with the latest metamorphis occurring in the 21st century. Now a hip location for residents and tourists alike, the area is occupied by cafes, restaurants, specialty shops, and nightclubs. Leaf and Bean Strip has called the area home since 2003.

As Mike and I meandered down Penn Ave toward 22nd street, we noticed a large mural on a building wall that wraps around Penn and 22nd. A sign on the corner of the building notes that Leaf and Bean is nearby. As you make a left onto 22nd street off Penn Ave, the mural continues and there is another sign pointing you to shop. The shop is hard to miss with its multi-colored brick front, corrugated steel awnings, and stop sign in the center.  The name Leaf & Bean is located above the awnings using steel letters.

Leaf and Bean Strip

Entering the Shop

As we entered, it was instant optical overload! This is most certainly the creation of Island Jim Robinson. You could stay there all day and still not take in all the visuals that are presented. I would describe it as “ordered chaos” and I am sure every object in the lounge holds a story that Island Jim could tell. As my eyes adjusted, Melody greeted us with a warm smile and handshake, welcoming us to Pittsburgh’s tropical getaway. We got some Cuban coffee and I proceeded to take some photos, and then some more photos. It was hard to decide where to start, as each time I took a photo, I noticed another eclectic object that deserved to be shown.

Leaf and Bean Strip

The Humidor

Once I completed some shop photography, it was time to visit the humidor. Being owned by Island Jim, the first cigars you notice are the Leaf brand,  front and center and easily identified with a bold red and white sign.

The humidor is chocked full of cigars, with many from small and medium size boutique brands. Island Jim is known as the kind of man that will give anybody a shot and his humidor is representative of that mantra. I also liked that there was a digital hygrometer/thermometer so you can see the actual conditions of the humidor – in this case – 70% RH and 64 Degrees F.

Leaf and Bean Strip
Leaf and Bean Strip

Island Jim Private Lounge – Lawrenceville

After we sat and talked some more, Melody invited to take us over to the Lawrenceville section of Pittsburgh, which is a just a short drive. It is here that Island Jim has set up a private, members only lounge. As we drove through the streets of Pittsburgh, we got the chance to see how the town is continuing to transform. We drove down a side street and back alleyway to arrive at the private lounge. With a click of a button, Melody opened the garage door of the house structure and drove in to where the lounge begins.

There is a wooden staircase that leads you up to a loft looking over the garage area. This is your first introduction to the lounge which is a stark contrast to the Leaf and Bean Strip shop. It is handsomely decorated with comfortable chairs, couches, tables, flat screen TV, and art work. Illumination is provided by rows of hanging lights and there is a small tiki bar in the back. There is more order to this area than the Leaf and Bean Strip but it still has Island Jim’s fingerprint on it.

This is certainly a comfortable place to sit and smoke a cigar and be out of the hustle and bustle of a shop. But this is just the beginning. Being a house, there are more rooms and Melody proceeded to take us further in. We walked up a set of steps and walked through a door and yes, there is more! A lot more!

There are multiple sitting rooms, each bedecked with numerous pieces of art, many of which Jim acquired when he was visiting Cuba. Each room had its own character and offered ample seating areas. There are two bathrooms. The first is a half bath with a toilet and a sink and the second is a full bathroom including a shower and a tub if you so desire it. The lounge even has a full, operational kitchen. There are lockers to store you private stash and a office space if you need to take calls or work while there. 

The Island Jim Private Lounge – Lawrenceville has a monthly membership fee of $225.00 which gets you 24 hour access, a bundle of any Leaf cigar each month, and a locker. In case you  need a cigar when there, they have a humidor that is filled with many popular brands and is based on the honor system where you write down what you took from the humidor and get billed monthly for. 

A Sincere Thank You

So, if you live in the Pittsburgh, PA area I probably don’t have to tell you about Leaf and Bean Strip, but if you are visiting on business or pleasure, I highly recommend you stop in. I have known Island Jim for years and on behalf of Mike Bruce and me, allow me to say thank you very much to Melody for taking time, on my 59th birthday, to give us the grand tour of Leaf and Bean Strip and the Island Jim Private Lounge – Lawrenceville. It was an epic start to the last year of my fifty’s.

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