When people think of Broadway Cigar in Northeast Portland, one of the first faces that comes to mind is Jonathan Gilat.

 

For years, Jonathan has helped customers navigate the world of premium cigars with an easygoing personality and an impressive depth of knowledge. Whether someone is purchasing a rare box for their personal collection or simply looking for their very first cigar, he approaches every conversation the same way. He listens first, asks thoughtful questions, and takes genuine interest in the person standing in front of him.

 

It's an approach that has earned him the respect of Portland's cigar community, but Jonathan's story stretches far beyond the walls of a cigar shop. Long before he became one of the city's best-known tobacconists, he was a young boy growing up in Tel Aviv, Israel.

 

Born and raised in Israel, Jonathan spent the first thirteen years of his life surrounded by a culture that continues to shape him today. His father worked in investing while his mother was a physiotherapist, and together they raised Jonathan and his younger sister, Romi. Like most children, he didn't spend much time thinking about how dramatically life could change. That changed in August of 2009 when his family made the life-changing decision to immigrate to the United States.

 

The Gilat family settled in Plano, Texas, where Jonathan entered middle school. Although he already spoke English and had visited America several times growing up, moving across the world was far more difficult than simply learning a language.

 

"The language wasn't the hard part," Jonathan told me. "The school system was."

 

Starting over at thirteen years old meant learning far more than classroom routines. He had to navigate a completely different culture, understand new social norms, and build friendships from scratch. The transition wasn't always easy. Jonathan remembers that Americans often seemed more reserved than the people he had grown up around in Israel, and finding his place took time.

 

 

Looking back now, however, he wouldn't change it.

 

"It opened up more options," he said.

 

While America became home, Israel has remained an important part of who Jonathan is. His childhood unfolded during a difficult chapter in the country's history, and even at a young age he remembers turning on the television to see reports of bombings at cafés and restaurants. Those moments left a lasting impression

 

."You always kept your head on a swivel," he recalled.

 

Living through those years taught him lessons that can't be learned in a classroom. He developed an appreciation for peace, an awareness of the world around him, and a resilience that still influences how he approaches life today.

 

When Jonathan reflects on the people who shaped his character, his thoughts immediately turn to his grandparents, especially his paternal grandfather. Long after his grandfather's passing, the values he instilled continue to guide Jonathan every day.

 

"The way you treat people is the way you want to be treated," Jonathan said. "That's the biggest lesson."

 

That philosophy is evident within minutes of meeting him. Customers aren't simply transactions. Every person who walks into Broadway Cigar is treated with the same respect, whether they know everything about premium cigars or have never cut and lit one before. Jonathan never tries to impress people with what he knows. Instead, he enjoys sharing what he's learned and helping others discover a hobby that has brought him countless friendships.

 

Ironically, cigars were never part of the original plan.

 

After graduating from high school, a family friend returned from Cuba and introduced Jonathan to premium cigars. At the time, he wasn't much of a smoker and never imagined the hobby would one day become his career. That changed after he moved from Dallas to Portland in 2016.

 

Jonathan's father introduced him to the owner of Broadway Cigar, and in 2019 he was offered a position at the shop. Like any profession, there was a tremendous amount to learn. He immersed himself in every aspect of premium cigars, studying wrapper leaves, filler tobaccos, countries of origin, construction methods, and the subtle differences that give each blend its own unique character.

 

 

Over time, customers began seeking out Jonathan specifically because they trusted his recommendations. They knew he wasn't trying to sell the most expensive cigar in the humidor. He simply wanted each person to walk away with something they would genuinely enjoy. That honesty has become one of the reasons so many people continue to ask for him by name.

 

More importantly, Jonathan discovered that the cigar itself was only part of the experience. The real reward came from the conversations that followed.

 

The relationships Jonathan has built through Broadway Cigar are what have kept him in the industry for so many years. Over time he has met people from nearly every walk of life, including military generals, professional sports coaches, business owners, doctors, retirees, and young professionals. Some stop in for only a few minutes, while others spend hours sitting in the lounge talking about life, family, careers, and everything in between. Every conversation is different, but each one reminds Jonathan that everyone has experiences worth sharing if someone is willing to listen.

 

He believes cigars naturally create an environment for those conversations. Unlike many hobbies that revolve around speed or competition, smoking a cigar requires people to slow down. Phones are set aside. Schedules become less important. Conversations become longer and more meaningful. Complete strangers often find themselves talking like old friends by the time the cigar reaches its final third.

 

"I've met people from all over," Jonathan said. "Military generals, athletes, business owners. You never know who's going to walk through the door."

 

Those conversations have become one of his favorite parts of the job. While premium cigars brought people into the shop, it was the relationships that kept bringing them back. Jonathan has come to realize that many people aren't simply looking for a good cigar. They're looking for community, conversation, and a place where they can slow down for an hour and simply enjoy being present.

 

As much as he enjoys the cigar industry, Jonathan doesn't see it as his final destination. His greatest professional ambition has always been education.

 

"I love learning, and I love teaching," he said.

 

History has fascinated him for as long as he can remember. While many people think of history as memorizing dates and names, Jonathan sees it as the story of humanity. Every civilization, every war, every invention, and every political movement helps explain why the world looks the way it does today. Understanding history, he believes, gives us a better understanding of ourselves.

 

When I asked him what historical period he could teach for an entire semester, he didn't hesitate.

 

The Thirty Years' War.

 

Fought between 1618 and 1648, the conflict reshaped Europe politically, religiously, and culturally. Although it receives far less attention than the American Revolution or World War II, Jonathan finds it endlessly fascinating because of the enormous impact it had on the modern world. Listening to him explain the subject, it's easy to picture him standing in front of a classroom someday. His enthusiasm is genuine, and his love for learning is contagious.

 

That same curiosity has also fueled his passion for travel. Among all the countries he has visited, Japan has left the deepest impression. He admires the country's emphasis on respect, honor, cleanliness, and efficiency. He appreciates being able to travel almost anywhere using public transportation, and he enjoys the sense of calm that seems to accompany everyday life there.

 

"It feels relaxing," he said.

 

Although Israel and Japan are vastly different cultures, Jonathan appreciates both because they have taught him different ways of looking at the world. Travel, for him, isn't simply about sightseeing. It's about understanding people, observing how they live, and returning home with a broader perspective than when he left.

 

Toward the end of our conversation, I asked Jonathan who he would most like to share dinner with if he could choose anyone from history.

 

His answer came almost instantly.

 

"Winston Churchill."

 

Jonathan has long admired Churchill's leadership during World War II and the resolve he demonstrated during one of history's darkest periods. There's also a personal connection that makes him smile. The two happen to share the exact same birthday, November 30. If Churchill weren't available, Jonathan quickly added another name.

 

Mark Twain.

 

Twain's wit, observations about human nature, and ability to tell unforgettable stories have always appealed to him. Looking back, it's easy to see why Jonathan chose those two men. Both were lifelong students of history, gifted communicators, and individuals who understood the power of ideas and conversation.

 

Before we wrapped up our interview, I asked Jonathan the question that concludes every feature in this series.

 

My website is called Everyone Has a Story.

 

What does that phrase mean to you?

 

He paused for only a moment before answering.

 

To Jonathan, every person is shaped by experiences that nobody else has lived. The places we grow up, the people who influence us, the hardships we endure, and the decisions we make all become chapters in a story that is entirely our own. Some stories are dramatic. Others are quiet. Every one of them is worth hearing.

 

Jonathan's own story is a perfect example.

 

It begins in Tel Aviv with a young boy whose family took a leap of faith by moving halfway around the world. It continues through the challenges of starting over in Texas, finding unexpected opportunities in Portland, and building a career centered not simply on cigars, but on people.

 

Today, many know Jonathan as one of Portland's cigar legends. Those who know him best understand that his reputation wasn't built on selling cigars alone. It was built on treating people with respect, taking time to listen, and recognizing that every person who walks through the front door has a story worth telling.

 

Perhaps that's the greatest lesson Jonathan Gilat has to offer.

 

Sometimes the best conversations don't happen because someone asks the perfect question.

 

They happen because someone is willing to slow down long enough to listen.

 

Thank you for your time, friend. I appreciate sharing your story.