With Toronto city hall looking to the Ontario Superior Court for solutions to regulating Uber, the court appears to be pointing the finger back at the city.

The legal battle between the City of Toronto and Silicon-Valley-based company began Monday, with the city arguing in court that the UberX service operates as an illegal taxi brokerage and should be shut down.

The case plays out amid a backdrop of massive protests by taxi drivers and political gridlock at city hall as councillors struggle with the question of regulating the new technology.

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Led by Mayor John Tory, council voted last month to suspend debate over taxi licensing until after the outcome of the court case.

But Justice Sean Dunphy turned the tables back on the city Monday, repeatedly questioning whether the issue should be dealt with in court and asking whether Toronto's "somewhat antiquated" regulations adequately "fashion a net" to enforce against and regulate technologies such as Uber.

"Why should we be arguing about this if it just takes the political will of the politicians to say exactly" how they want the issue handled, Justice Dunphy asked as city solicitor Michele Wright outlined her arguments.

He referred to the heated debate over taxi licensing happening outside the courtroom – including hundreds of taxi drivers who shut down city streets on Monday morning to protest against Uber – and said it was the place of politicians, not the courts, to make decisions about regulating the technology.

In the past, Mr. Tory has expressed support for Uber, saying it and similar technology are "here to stay."

"The mayor has said that he wants to regulate, which is not what this is doing," Justice Dunphy said.

He also appeared skeptical at the city's argument that UberX, an app that brings together passengers with paid private drivers, constitutes a taxi brokerage.

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Just as an Air Canada call centre in Bangalore is not operating an airline but a call centre, Justice Dunphy said, so, too, does Uber appear to offer ancillary services and not the service itself.

The judge also questioned why the city is going after Uber, which calls itself a technology company and not a taxi service, and not the individual drivers who are operating without proper licences and insurance. "You're finding it very difficult to catch each and every one of those fish in your net, and you'd rather catch the godfather," he said.

The UberX app does not abide by local regulations that require taxi drivers to hold commercial insurance and licences. The company has in the past asked for the creation of new regulations to account for the service it provides.

Sam Moini, a representative of the Toronto Taxicab Alliance, said taxi drivers are frustrated with being caught in the middle between the courts and city hall. An estimated 1,000 drivers clogged downtown streets around City Hall and Queen's Park on Monday morning to express their frustration at Uber, and the mayor's stance on the company.

"We're following the rules, and they're not and they're not being punished," Mr. Moini said.

Uber Canada spokeswoman Susie Heath issued a statement on Monday saying that the company is "fully committed to working on a regulatory framework for ridesharing," and that "stopping Uber's operations in the city will not promote public safety or improve urban mobility for Torontonians."

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The case returns to court on Tuesday.