A Cowboy, Some Cigars, and Malört

A Chicago story about neon, skulls, and human connection.

I'm so tired of influencer culture.

I didn't say "I'm so tired of influencers" because that would be too honest mean. But for sure the culture surrounding it.

From how we write, to how we interact with others, and in my world even in how we lead in a church, we are so quick to offer something. I have something for you that you can't figure out on your own, but I did, so let me share it with you.

I read something the other day about how we should normalize writing personal experiences and stories instead of countless curated advice pieces.

Wow, I want that.

I want to know what it felt like to go through some of your biggest moments, the good and bad, because most likely I have felt something very similar in my own moments. That's a beautiful thing about humanity. We may walk significantly different paths, but when we hear about an experience from someone, we can (and probably should) find ourselves feeling a little bit of what they felt. It might be a feeling vicariously through someone, but I think that might be a good thing most of the time.

Feeling what others feel could also build empathy in us for others, and since this is not a curated advice piece, I won't say that you and I could use more empathy in our lives. I won't.

So, here's a story:

I remember vividly a few years back sitting on the couch thinking about the long summer days beginning to wane, the light at the end of the tunnel after being stir-crazy from a year of staying home and relatively isolated, and how in just about one month we'll be trapped (again) by a calendar set for us by the education system.

Summer of 2021 for me felt like a caterpillar finally able to exit the cocoon and spread new wings, only to find itself in another cage, but not of its own doing. It felt a little bit like the way you feel during an MRI as you get conveyed out of the tube but know you have to return to your hospital room instead of home. Or even the way a lost cave explorer might feel as they finally make it to the light they've been following but realize they've only made their way to a bigger, and still far underground, room.

We were able to visit family in Texas earlier that summer, but hadn't planned any vacations because we simply didn't know what travelling would look like as the world was slowly crawling out of the Covid-19 shut downs. In fact, we had trips to Paris, Toronto, and Hawaii all cancelled over the last 12 months and we were still a little gun-shy to plan something again.

But sitting on the couch on that Monday night, Jess and I decided to surprise the boys the next morning with a road trip to Chicago. We looked around at hotels and Airbnbs and decided to just book a hotel on the way there, hoping we'd land a good location for a good deal. Our plans?

Wander. Experience. Eat. Drink. Play.

We woke the boys up a little before 4am on Tuesday, and were back home by Thursday. If you were to ask anyone from our family to list their top 3 vacations we've taken, this short, two-and-a-half-day trip would be there for most of us.

The weather was perfect and we walked everywhere. We did a lot of the things one does when visiting Chicago, and a lot of things that maybe aren't the norm. We walked across the bridges, took pictures by the Bean, visited the Navy Pier and rode on the ferris wheel, went to the tall building and did The Tilt experience, found a swanky rooftop bar, went to the big parks and found the small neighborhood playgrounds, found small coffee shops and the massive Starbucks Reserve, ate Chicago style pizza, went shopping, laughed, spent time together, and explored. It was so special.

The first day there felt like a week of existence in the best way. We arrived in the city around 9am and found a hotel for the next few nights. I won't go through the day, because all of this isn't really about our trip.

This is about a moment of a tiki bar, a cigar, a cowboy, and Malört.

Walking home the first night, all of us were exhausted from the day's adventure. The kids were 6, 9, and 11 at the time, and we walked over 22,000 steps that day. But even for Phoenix, the youngest, instead of irritation and melt downs, the end of the day brought a tiredness wrapped up with a blanket of a day well spent.

We had just finished a deep dish pizza at Lou Malnati's Pizzaria and were trying to make it home before the sun disappeared. Thankfully this was the middle of July: the height of early sunrises and late sunsets. On the way home we passed a cigar shop, some restaurants, and near the final turn to our hotel, I looked down an alleyway and saw a bright neon sign that simply said "bar". No door in sight from my view.

I'm an introvert who loves spontaneity, change, and to exist as a no one surrounded by everyones. So that neon sign was calling my name, to simply just see what it was, but we were tired and kept walking to our hotel.

When we got in, I thought about that cigar shop and that neon sign. It would be nice to grab a cigar for sometime the next day. It would also be nice to see beyond that "Bar" sign. I don't remember all that entailed, but I mentioned my thoughts, and Jessica, knowing me well, simply said something like "Go check it out. I'll handle bath time".

So I went for a walk.

It was a quick one. Down the elevator of the hotel, out the doors, and down the street. Dark was settling in, and the neon was burning bright. I walked down the alley and came upon a man standing below the sign, next to an open door that led to a stairwell down. I sent Jess a quick text: "I'll FaceTime you the whole time".

I almost turned back.

I wasn't going to get a drink or food, I simply wanted to see beyond. I wasn't sure if this was an exclusive bar, an extension of the restaurant out front, and was hoping it wasn't a club of a nefarious type (it wasn't).

The man blocking the stairs wasn't a host for a restaurant. He was a bouncer. And he was big. I gathered my words and said something like "Hi, would it be ok if I simply went and took a look at the bar? I probably won't stay, just exploring." The outline of color on the man was a mixture of a pink glow from above, an orange glow from the setting sun, and a blue glow from the stairwell behind him. He was kind, checked my ID, and waved me through.

He pointed me toward the door, and as I entered I saw death.

I mean not actual death, but the wall the stairwell descended beneath was covered with skulls and that blue light glow. It was like an ode to the Catacombs of Paris, and set the tone to the place just right. I finished the stairs, took a turn left and saw what I had wanted to see. It was a tiki bar, and looked like a fun stop for a date night, but not a place for three kids to join.

Turns out it was a fairly well known speakeasy / tiki bar in Chicago called Three Dots and a Dash. I walked around a little bit inside, and then made my way out. As I passed the bouncer at the top of the stairs, a quick head nod exchange was all that was needed.

I made my way out of the alleyway and to the cigar shop. By now the summer day couldn't hold on any longer, and it was nighttime in Chicago. The shop had a few chairs out front with its glass door propped open. There were a few people outside smoking a cigar, and a few people inside.

I enjoy a cigar every now and then. The slowing down, the deep breaths, and the scent of the tobacco smoke all create a unique moment in time. I've also had most of the cigars in my lifetime with my dad, and that is always sacred.

I am no connoisseur. I know the name of a few cigars that I enjoy, so my default question in a tobacco store is "Hi, I don't know much about cigars, but I know I like the Foundation Tabernacle. Do you have that, or a few in a similar vein as it that you could show me?"

I find that not pretending to know more than I do in a cigar shop (also everywhere) is disarming. No one wants to help a know-it-all. Good people want to help someone with questions. And truly, most people are good.

The man working behind the counter had a few follow up questions: How long of a smoke are you looking for? Do you like flavored or want to stay close to the Foundation brand? Do you want to smoke it here?

I hadn't really thought about smoking a cigar here. I was thinking of buying one and maybe finding time on day 2 of Chicago to enjoy it, or even bring it home with me. My answers were: Under 30 minutes, No flavored cigars, and Sure, I'll smoke it here.

I don't remember what I was given, but I paid for it, he cut it, and then a man wearing cowboy boots and hat let me borrow his lighter to light it. His hand, dark and deep brown, calloused and steady, extended the flame toward me. He had just lit his cigar and said I could join him in the chairs outside of the shop.

There were a few chairs open and so we sat, I gave him his lighter back, and then we introduced ourselves. I sent Jessica a text: "I'm smoking a cigar. With my friend Jay."

Jay was in his late 50s to early 60s, a lifelong flight attendant with Southwest airlines, and Chicago (and this cigar shop) were one of his favorite places to overnight for work. I asked about his travels, and he asked about my family. We heard stories from strangers over cigars.

I remember at one point, when my cigar was close to being done (and I needed to head back to the hotel), that he asked me if I've ever tried Malört. I had never heard of that word before, so my answer was obviously "no sir, I have not". He went on to tell me it's tale.

For decades, Jeppson’s Malört was this obscure, dusty bottle behind Chicago dive bars. Nobody ordered it except old Swedes, masochists, and bartenders hazing outsiders. Over time it stopped being "the worst liquor ever" and became a piece of Chicago's identity.

Thankfully, he told me how terrible it tasted, and how every Chicagoan insists you try it at least once. He stood up and said "Let's go across the street to the pub. I'll buy you a shot before you head back."

Jay stood up and began walking across the street. His boots clicked on the concrete as he walked with a slight limp.

This is the moment in movies that you look at the screen and think about how dumb that character must be to just go along with the ploy, or think about how lazy the writer was to let things unfold in such a familiar way. Everyone knows this is the oldest trick in the book and a sure fire way to end up as a bad headline in the news.

I got up and followed him.

He rested his still lit cigar on a post outside of the pub, I extinguished mine, and we walked inside. It was packed. He greeted the bartender by name and they talked like old friends for a few minutes. He then introduced me and said something like "This is my new friend Trae's first time in Chicago. He needs to try Malört". The bartender smirked a little bit as she grabbed three small shot glasses, a bottle from the shelf, and filled each up.

This moment did kind of feel like the movies, but not the scary ones.

It felt like those scenes where people are living. They're not overindulging and forgetting. They're not slurring and coping. Living.

We (Jay, the bartender, and me) raised the glasses and downed it. People around clapped and smiled and said things like "Now you've been to Chicago" or "Isn't that terrible??"

It wasn't terrible, but it was bad. Thankfully, I think I was well prepared so was able to tough it out.

Time had passed quickly, and I needed to head back to the hotel. I thanked the bartender, said my goodbyes to Jay, and made the short walk back.

Nearly four years later, I still think about this experience. The mixture of intrigue, exploration, skulls, a good cigar, human connection, and a bad liquor made for an elixir that comes around every now and then in life, just maybe in different forms. Sometimes you have to look for it. Sometimes it might show up on its own.

And I'd take that any day over what an influencer is trying to offer me.