In 1996, alleged triad leader Lai Tong Sang and his family were admitted to Canada, when an immigration officer failed to check into his background.
It did not take authorities long to concede that their entry was a mistake, attributed in a government-commissioned investigation to an overworked employee in Canada's consular offices in Los Angeles.
But 17 years later, Mr. Lai still maintains a residence in Richmond, B.C., and the long delay in Canada's efforts to have him turfed out continues to hang over recent proceedings against the man said to be leader of the Shui Fong Triad in Macau.
In a final, written submission to the Immigration and Refugee Board, Mr. Lai's lawyer, Peter Chapman, noted that Canadian authorities have had evidence of his alleged activities as far back as 1997.
"Why has [this been raised] with respect to Mr. Lai now, many years after the fact?" Mr. Chapman demanded. He speculated the action was being used to thwart Mr. Lai's bid to become a Canadian citizen, which has been pending since 2001.
James Bissett, who conducted the investigation into Mr. Lai's admission many years ago, has expressed shock that Canada waited so long before trying to have him deported.
Not long after Mr. Lai arrived in the Vancouver area, he was the target of an unsuccessful drive-by shooting that police have termed an attempt on his life by rival triad leader Broken Tooth Koi.
Evidence presented at a board hearing earlier this year said the contract to eliminate Mr. Lai was worth $1-million Hong Kong ($132,000).
The hearing also heard from several witnesses attesting to Mr. Lai's leadership of Shui Fong. They testified the Macau-based triad took part in killings during a violent turf war in the 1990s, as well as loan-sharking, extortion and prostitution, basing some of their assessments on sources within the Macau police force.
In her response to Mr. Chapman's submission, government lawyer Becky Chan pointed as well to numerous media articles and books identifying Mr. Lai as the triad's so-called dragon head.
"There is ample, credible and trustworthy evidence" to establish the reasonable conclusion that Mr. Lai was a Shui Fong member," she concluded.
Canada is seeking Mr. Lai's expulsion under a section of the Immigration Act that says membership in a criminal organization renders non-citizens inadmissible to the country.
But Mr. Chapman called on board member Geoff Rempel to dismiss the case, arguing it is based on hearsay, that the Macau police force at the time was riddled by corruption, and that journalists "may engage in sensationalism and manipulation."
"It is submitted that suspicion about particular activities are not sufficient to provide a reliable foundation for reasonable belief," he contended.
A decision on Mr. Lai's future in Canada is expected in August.