It isn’t often that Drew Dilkens shuts off his role as mayor and honestly, after speaking to him, I can see why. He is genuinely the “Windsor Man” right to the core.  

I catch him glancing out the City Hall windows that overlook the Detroit skyline, and even as the view is murky and covered with rainy fog, Drew looks delighted to be here, looking at our neighbouring cities and seeing what they have both become in the 12 years that he has sat on city council. 

Before his time in this job, Drew was always involved in the community. He says that even back in high school when he and his wife Jane Deneau were dating, he was the stereotypical guy on student council, while leading other clubs and organizations. 

“Some parents worry about their kids doing drugs, but I don’t know that my parents ever had that worry. It was, ‘Oh he’s coming home as the president of Crime Stoppers… at 19,’” he laughs. 

Like most teenagers, Drew’s interests were always changing. He once decided that he was going to become a police officer. 

He had applied a few times while in university and passed the physical. But his interviews never lasted more than two minutes. They kept telling him to come back once he was done university. 

He didn’t understand. He’d passed, what else was he missing? The experience did something for him though—it pushed him to finish his education. In the course of finishing his degree, Drew realized it wasn’t the career he wanted to pursue after all. 

It was all thanks to one particular call while he was volunteering with the Windsor Police Auxiliary. 

“We got a call on the west end in the middle of winter. It was so cold and when we pulled up all we could hear were people yelling and a baby crying. Inside, the kitchen had white walls. Now imagine taking a sponge and dipping it in red paint, then putting it into a towel and swinging it around. Ceiling to floor: it was all blood. So unbelievable. I still get goosebumps telling the story.”

It was the chaos of that call where all Drew could remember thinking was, “I can’t do this as a career.” He worked for 10 more years under this unique experience of being able to stand briefly in police officer’s shoes, of going for ridealongs every winter. He has a deep respect for what officers do—he’s seen the work firsthand. But it just wasn’t for him.

After that, he decided to become a lawyer. 

There was satisfaction in completing law school, and then in finishing his doctorate degree. It took sacrifice, but it still wasn’t Drew’s passion project. 

Drew’s passion was the city. 

And watching him sitting in his light shirt all done up neatly, pinned together with his signature red tie, still he seems comfortable and relaxed, as if this is exactly where he loves to be and is most himself when representing the city. 

He’d almost missed out on it, right before he ran for city council again in 2006. He and his wife Jane nearly moved to Belgium for a year. As lovers of travel and other cultures, they figured they could live there for one year and return with a new language under their belts. He especially wanted to go because of his father’s Belgian roots. But when Drew got the call that there would be space opening up for city council, Jane knew he would regret it if they ever left. 

This was his dream, and he’d worked too hard to just leave. 

And she would have been right. Drew belongs in Windsor. Even as he fulfills his other passion of travel, he looks for ways to bring insight and culture right back to his hometown. 

“I love my city, and I love Canada. But I love seeing other things, feeling something different, smelling other smells. All of the senses are engaged in a different way when you step out of an airport into a place where you’ve never been before,” he says. 

Travelling sparked in him a craving to go out and see something new, and it opened his mind to other schools of thought that he otherwise wouldn’t have had the chance to experience. 

Now, he and Jane try to get their two kids out to become citizens of the world. 

“I want them to feel like they’re not constrained to stay in Windsor. That they can go anywhere and do anything and feel like the world is open to them,” he says.  

Both his son Jack (14) and daughter Madison (17) were born in Detroit and have dual citizenships, along with having their EU passports. The parents have created opportunities for their kids to be able to travel anywhere in the modern world, especially having enrolled Jack and Madison in fully French schools right from kindergarten.

These travels expose Jack and Madison to fresh ideas and unusual conversations, which is exactly why Drew and Jane love to just hop in the car and drive off for the day.

“Let’s use the Tecumseh-Brock Monument for example,” Drew begins. “There was a lot of pushback from the community that we shouldn’t be investing in our history or spending our money on a statue. Many people didn’t see why it would be important, and I think a lot of that criticism came from people who haven’t been to cities that do it and haven’t seen what it means. Especially in European cities where statues are everywhere. It becomes part of the fabric of the community.”

Drew believes that these monuments, especially historic public art, tell an authentic story that makes up our city. If his children experience the world, they won’t shut down an idea right out of the gate just because they can’t picture it in their own minds. 

“We have to think of Windsor but also think bigger. We need to bring the best ideas back and think how you can incorporate them here in our community in an authentic way.” 

Aside from travel, there isn’t much spare time while living as the mayor, especially between having kids and getting things done around the house. It’s one of those jobs that Drew says, if done right, becomes a part of you. 

When he’s out, he doesn’t get recognized as “Drew”; he’s “The Mayor.” Even when he’s shopping at Costco. 

“It’s not a bad thing actually, you become accustomed to it. Frankly, for me, those conversations are nice, and people will rarely come up to you and be ignorant. It energizes me that we can talk about the city,” he says, as long as they can have a rational and civil conversation. But actually, the most common comment that Drew hears when people first see him is, “Wow, you’re so tall.” They don’t expect his 6’4” stature because Drew is normally caught sitting at a desk, or only half of him is captured in a photo. 

When I ask him, “What is the most interesting thing about you that we wouldn’t know from your resumé alone?” he says that he feels so un-Canadian in talking about himself, so he decides to call his chief of staff, Norma Coleman. 

“I have no audience to ask and I can’t do a 50-50, so I’m phoning in a friend,” Drew jokes. 

Norma’s answer is almost immediate. “In spite of your height, you were never a basketball or volleyball player, but a swimmer,” she says.  

We all laugh as our long conversation fades. Most of Drew’s campaign team even teases that he takes too long when he goes door-to-door, that he would happily talk to someone for 20 minutes. And they’re right. Despite how hectic his life is, he’s never too busy to have a good, engaging conversation with someone.