And it's a question that's been asked for close to six decades.
"We think there is opportunity to bring some new energy, new experiences, and new attention to Stephen Avenue," Marco De Iaco told the Calgary Eyeopener.
As the executive director of Calgary Downtown Association, he represents businesses that want to see change.
And depending on who you ask, there's lots of change needed.
Vacancy rates are considered to be among the highest in the city and have jumped a whopping 50 per cent since 2015, De Iaco says.
One in ten retail spaces along the pedestrian mall sit empty right now, which stretches from Olympic Plaza to Mewata Armoury.
"We think it's important to review the entire avenue," De Iaco said.
"We think we can do that with some smart, thoughtful planning."
But the starting point is finding some consensus on key questions.
"What do we want the experience to be, and how do we program that? Events, festivals, art? What infrastructure upgrades are needed? What policies might entice investment or encourage innovation?"
Public input sessions to look at possibilities and offer feedback are running this week.
A fourth-year urban studies student at the University of Calgary had a look Wednesday.
Brock Parksk who lives in the core, would like to see Stephen Avenue treated as more of a corridor from one side of the downtown to the other.
"I think there should be a new preference to pedestrians and cyclists. It could be a good way to bring new people down as well," Parks said.
Margaret Ellis has lived downtown since 1993.
"I am here two or three times a week because I just live around the corner," Ellis said.
"The more businesses we have, the better it is."
But the types of businesses the mall needs is the tricky bit.
"We have good crowds at lunchtime. We have lots of great restaurants but we definitely need more businesses."
Meanwhile, De Iaco says, while he gets some might question the timing of putting money into the mall, that's the point.
"We think this is exactly the time to be challenging the status quo, to try and bring some vibrancy to downtown Calgary."