Jennifer Mathieson peers over a pile of lumber that used to be a street bench.

It's one of dozens of pieces of property the executive director of the St. James Village BIZ said was damaged by snow-clearing crews along Portage Avenue on Wednesday.

She said that as careful as crews have been in the past, each winter business owners expect and plan for a little bit of damage. But she thinks the latest damage is different.

"We do plan for that. You do kind of expect that, but this is massive. This is nothing we've ever seen before, and I work with a number of the BIZ zones in Winnipeg … I can't recall the last time it was this bad," she said.

Mathieson said there's not a single strip in the 20-block St. James business zone that doesn't have some kind of damage, and estimates the cost of that damage will total more than $10,000.

She said the business association has insurance which should see the city cover the costs of the damage.

Brian Mitchell, co-owner of A Muse N Games on Portage Avenue, looks at a bike rack that was ripped out of the ground in front of his business. (CBC) Brian Mitchell, co-owner of A Muse N Games on Portage Avenue, said a bike rack was ripped out of the ground in front of his business. He said it is frustrating to see the damage.

"Knowing that it's tax dollars — both from the residents and the businesses — that go into an item like that, and then knowing that even if it's covered by insurance again … there's money coming out of taxpayer pockets," said Mitchell.

Mitchell stopped short of piling on to the plow operators. He said that after some of the heavy snowfalls this winter, some crews helped him clear out a path from his business to the road. That allowed customers and delivery people to reach the business without having to climb a five-foot hill of snow.

But Mitchell did call on the city to collaborate with business owners to find a better solution.

"I don't know if the city needs to work with the businesses where in the fall some of those bike racks and stuff are unbolted from the concrete only to be rebolted in the spring. I don't know whether that's more cost-effective than replacing some of the bike racks and other obstacles year after year," he said.

St. James BIZ executive director Jennifer Mathieson said not a single strip in the 20-block business zone escaped damage. (CBC) Mathieson said the BIZ already submits plans for all of their street improvements when the apply to the city for permits.

"They know what's out here and they have documentation to prove it," she said.

"My question is, why aren't people looking at this? Why aren't you preparing yourself and your crews to know what's out on the streets before they start removing snow that might be covering something of value?"

Mathieson also said the St. James BIZ is still waiting for an insurance claim for damage from last year that is worth approximately $5,000.

79 snow-clearing claims this year

A city spokesperson said 311 received a report regarding the damage, but since it is being investigated the city can't speak to the specific claim.

"For damage involving snow clearing operations, citizens are encouraged to report all vehicle claims to MPI and property damage claims to their property insurers to ascertain whether there is insurance coverage available to them," the spokesperson wrote in an email statement to CBC.

The city also has information on how to file a claim for damage online.

The spokesperson said if an investigation determines a city contractor caused the damage, the claim would be forwarded to the contractor.

The spokesperson said the city received 327 damage claims related to snow-clearing operations last year, and paid out $21,131.50. In 2015, there were fewer claims — 292 — but the city paid out $44,155.44.

The city says it has received 79 snow-clearing damage claims so far this year.