Chicago has come to be known as The Second City and that moniker is sometimes argued about. It seems to have a different origin and meaning. depending on who you talk to. Some say it refers directly to the 1889 Annexation which brought the population of Chicago to roughly 1.1 million people, thus making it the second largest population in the United States (New York being first). Others say that it is an homage to the rebuilding of the city after the Great Chicago Fire of 1871.
If you call Chicago The Second City, or even if you call Chicago home, the fact holds true that Chicago is an iconic city. From a vibrant arts and entertainment scene, to the incredible history in sports. Chicago also has amazing food that includes world famous deep-dish pizza, Italian Beef sandwiches, Chicago-Style hot dogs, and some of the best steaks on planet earth.
But what if you are in Chicago and looking for a great place to relax with a cigar and some good company? All-in-all, Chicago has a number of fine cigar shops, and they are well distributed throughout the area. But in October of 2018, Garret and I drove to Chicago to meet with Riste Ristevski. Riste is the owner and founder of Jas Sum Kral Cigars (JSK). Since Riste lives just on the Indiana side of Chicago, we talked about meeting at a shop in Chicago. Without hesitation, the first place he suggested was Biggs Mansion.
When Garret and I arrived in Chicago, the city earned its other nickname of The Windy City. The weather was blustery, with a cold wind that went right through us. We arrived at Biggs in the early afternoon and both of us were stunned right away with the look of the place. It is a beautiful old house that was built in the early 1890s. Looking at the structure made me feel as though I had gone back in time.
This beautiful old house had been painstakingly restored from many decades of neglect and disrepair. When Fred Latsko purchased the building, he put millions of dollars into the renovation, from a space that was dilapidated and sad with a stained suspended ceiling in the main level that was home to a restaurant. The renovation brought all of the spaces in the house back to their original splendor, and in some cases even more beautiful.
The entrance brings you into a fantastic cigar shop with a vast selection of premium cigars, and cigar accessories. Just past the retail counter is a modest lounge area that is open to the public. The rest of the second and third floor seating areas are for members only (day-passes for non-members are available for purchase). We were greeted by Pandi Naum, the manager of the shop and an extremely knowledgeable certified Tobacconist. He walked us through the humidor and helped us choose our cigars before we headed upstairs to relax.
When arriving on a floor after walking up the beautiful curved staircase, the entire house seems endless. Every turn around a corner, or walk through a door reveals another lounge space, each more stunning than the last. No matter which room I would enter, it was a space that would make Ron Burgundy proud. The rooms are all filled with plush leather furniture and rich mahogany woodwork. Each table is adorned with a perfectly clean ashtray and a box of matches.
Each space has its purpose. While many of the rooms are arranged in a conversational layout, some have large televisions for watching the game. Other rooms have bars and groupings of smaller tables that would be suited to private cocktail parties. There is a billiard room and also a few rooms that would work nicely as corporate conference spaces. Every room is beautifully appointed and well cared for. It is easy to tell that the ownership and staff take pride in this place.
We chose our space to relax and have a nice conversation with Riste. Truth be told, we recorded all of it for podcast and Youtube, but the audio quality was absolutely terrible so we had to scrap all of it (we had our fair share of technical problems when trying to get HBTC off the ground). Honestly, even though we can’t share the interview with you, we had a great conversation.
To be able to relax in a comfortable setting and just talk is a rare thing today. As we become more dependant on our mobile devices, we lose the art of the conversation. We also lose the value of relationships, and that’s what it is all about. As posh and fancy as Biggs Mansion may be, it all boils down to the relationships we have. When we put the effort and the time into those relationships, the rest is all just a bonus.
If you find yourself in the Chicago area, you honestly need to visit Biggs Mansion. It is becoming one of the most iconic cigar destinations in Chicago. As far as we are concerned, it should be known around the world. From the selection, to the friendly and knowledgeable staff, to the incredible lounge spaces, you will be a happy cigar smoker at Biggs.