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The gunfire rang out on a summer night in 1997, terrifying neighbours, worrying police and briefly bringing to public attention a man purported to be the crime boss of a feared triad in Macau.

Target of the drive-by shooting was the southwest Vancouver residence of Lai Tong Sang, who had been let into Canada by mistake just nine months earlier.

Now, newly available wiretap information indicate that, indeed, a triad war in Macau did spill over into Vancouver upon Mr. Lai's arrival. The information, contained in court submissions obtained by The Globe and Mail, is expected to form part of the government's argument to have Mr. Lai kicked out, nearly 17 years after he landed here under the country's immigrant investment program.

At the time, Mr. Lai was considered by Macau and Hong Kong police to be the "dragon head" of the Wo On Lok Triad (also known as Shui Fong), then engaged in a violent turf war with the 14K Triad.

But an immigration officer at Canada's Los Angeles consulate admitted him without making a thorough check of his background.

Despite the drive-by shooting and Mr. Lai's long-time reputation as a triad kingpin, however, Canadian officials have moved only within the past 18 months to deport him, alleging that he belongs to an organization engaged in criminal activity. An Immigration and Refugee Board hearing on the matter is set for Feb. 26.

Critics point to the case as yet another example of the glacial pace of evicting immigrants who came to Canada improperly.

In a 2011 report outlining its reasons for seeking Mr. Lai's removal, the Canada Border Services Agency defended the lengthy delay.

Investigating members of organized crime is difficult, since they are often "sophisticated, very mobile, have access to vast resources and use violence or threats to intimidate witnesses," the CBSA contended.

The agency also disclosed that "new releasable" wiretap information gathered by Hong Kong police was now available, pointing to the drive-by shooting as a gangland attack on Mr. Lai.

"A 14K Triad member in Hong Kong asked 14K members in Vancouver to murder Lai because of the Shui Fong and 14K dispute in Macau," said the report.

"[In] one conversation, the Hong Kong 14K member explained there was an ongoing battle between them and Shui Fong members and that Lai had fled to Canada," the report stated. "Then the wiretap detailed the phone call from 14K Triad members deciding if a contract should be put on Lai."

The report was submitted to the Federal Court of Canada as part of a response to a court challenge by Mr. Lai's lawyer, Peter Chapman.

Mr. Chapman claimed that seeking his client's removal so long after he came to Canada was "unreasonable and prejudicial." The court dismissed his application for leave to seek a judicial review.

Mr. Lai, who turned 58 earlier this month, is a citizen of Portugal, which ruled Macau until 1999, when the colony was returned to China. Since then, Macau has grown into the largest gambling enclave in the world, with annual revenue five times that of Las Vegas, and media reports from Macau maintain that Mr. Lai is still a big player there.

At the height of Macau's triad wars in the mid-1990s, Mr. Lai applied at Canada's Hong Kong consulate to enter the country as an immigrant investor. When immigration officers stalled his application over concerns about his alleged triad involvement, Mr. Lai tried again in Los Angeles.

This time he succeeded, when the person who processed the application failed to check Mr. Lai's history with Canadian officers in Hong Kong.

A subsequent investigation commissioned by the then-Liberal government blamed the gaffe on overworked staff handling too many applications.

Mr. Lai landed at Vancouver International Airport on Oct. 28, 1996. He and his wife and three children have had a residence in the Lower Mainland ever since.

Critics are aghast that Mr. Lai is still here.

"The wheels of justice grind terribly slowly," said James Bissett, the retired diplomat and former immigration department director who conducted the probe into Mr. Lai's admission.

"I'm shocked that it should have taken so long [to have him removed]. I'm happy they are taking action at last, but reforms are desperately needed."

Liberal immigration critic Kevin Lamoureux said he's amazed Mr. Lai remains in Canada.

"It's totally unacceptable. There's no reason for it, just because a mistake was made," said Mr. Lamoureux.

The CBSA report cited a litany of sources alleging that Mr. Lai was head of Wo On Lok, which, according to an affidavit from a former Hong Kong Immigration Control Officer, was involved in loansharking, extortion, assault, gang fighting, and illegal gambling."

Asked by The Globe whether his client, Mr. Lai, belonged to a triad, Mr Chapman replied: "I can't comment on anything to do with current proceedings, because it's in process."

In his submission to the Federal Court, however, Mr. Chapman argued: "It is not an indictable offence to be sworn into a secret society or engage in a 'turf war' with another organization."

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