Can Windsor rebrand itself as a hip place to live and work like Detroit has?

In 2013, Detroit became known worldwide for being the largest city in America to ever file for Chapter 9 bankruptcy.
Just over two years later, the gritty city has done what some back then would've thought was unthinkable: It's branded itself as an exciting city on the rise. 

Windsor's neighbour across the river has gotten glowing write-ups about its gentrification efforts in the likes of The New York Times and Vogue. Young hipsters seem to be eating it up, with reports of some flocking to Detroit to be part of rebuilding a once-great city. 

A man working on a plan

Now, Windsor is on the verge of its own image makeover. Mayor Drew Dilkens has made rebranding Windsor a key part of the city's 20-year strategic vision.

In the coming weeks, city council will reach out to Windsorites to get their take on how to brand Windsor over the next two decades. In an interview with CBC News, Dilkens said he was hoping to change the conversation because Windsor is still seen as "that we're that rust-bucket, sort of lunch-bucket town, but the people who live here know that that's not true."

Perception is reality

Windsor has dealt with some serious perception issues over the years. Back in 2007, around the same time comedian Stephen Colbert jokingly implied Windsor was the worst place on Earth. Marketing guru Ed Roach asked people in a blog post what they thought of the city. The responses were mostly negative, he said, with some saying the city was "dirty" and "boring."

While Roach has lived in the Windsor-Essex area for decades and loves it, he does not discount the negative things he's heard from both locals and outsiders over the years/

Perception and reality are the same thing when it comes to branding, said Roach, the head of The Branding Experts, in a phone interview.

Repping our city 

The reality is, anyone who lives or visits here knows there are many great things to do in the area, such as visiting the nearby wineries, grabbing a beer in Olde Walkerville or taking a rum-running tour, said the marketing expert. But, the unemployment rate has been stubbornly high for years and that's led to some negativity among young locals. 

In response to this negativity, Ayad Saddy, owner of BB Branded Boutique, decided to sell T-shirts with the positive slogan: Win City. 

"Over the years, when you're chipped downwards you can only build it back up the same way," said Saddy by phone. 

He is hopeful his popular line of tees can be part of encouraging young people to '"rep our city."

Advice from across the river

Over in Detroit, organizations like Opportunity Detroit, funded by billionaire Dan Gilbert, have lessons to share. 

Lisa Dancsok leads Opportunity Detroit, which aims to attract businesses, residents, and visitors to the city. Dancsok said Windsor should look to other cities, such as Austin, Tex. for inspiration. She also recommended Windsor focus on providing interesting and exciting job opportunities for young people.

What's good for the goose, is good for the gander

These days, there is a lot of fascination with Detroit, said Vincent Georgie, a marketing professor at the University of Windsor. And that's an opportunity for Windsor.

"We're able to cash in on some of the curiosity around Detroit without actually having to face anywhere near the socio-economic problems Detroit is facing," he said in a phone interview.

The W?

Dilkens sees the city, known to some as The D, as a source of inspiration. 

"I think Detroit has done a fantastic job in their branding, you just think of 'The D,'" said Dilkens. "It's so simple ... but they're able to use it in such clever and creative ways ... I think it's something like that that Windsor wants to come up with."

Possibly coming up a new city nickname is just one part of the plan to rebrand our city over the next two decades. It will certainly be exciting to see what The D and in The W(?) city brands are like in 2035.