But in newly released written arguments, Lai Tong Sang's lawyer said that Ottawa is basing its arguments on multiple layers of hearsay evidence that is unreliable.
Lai, his wife and three children, became a permanent Canadian resident in 1996, but it wasn't until 2011 when the family asked for citizenship that the federal government moved to eject them.
Last February, an immigration adjudicator in Vancouver heard evidence that Lai was the leader of a Macau triad, had ordered the murders of three of his gang rivals and that another rival had taken a contract out on Lai's life.
Documents submitted by the minister of Public Safety to the Immigration and Refugee Board say Lai and his family should be deported.
"There is ample credible and trustworthy evidence to establish that there are reasonable grounds to believe Mr. Lai was a member of the Shui Fong triad in Macau."
The submission states Lai is alleged to have taken part in a pattern of activities that would be an indictable offence if they were committed in Canada.
"Furthermore, documentary evidence and the testimony of the minister's witnesses demonstrate there are reasonable grounds to believe that the Shui Fong triad in Macau engaged in activities such as loan sharking, killing and assaults."
Evidence presented at the hearing said a police wiretap overheard evidence that a contract was being taken out on Lai's life over a turf war with the so-called 14K gang.
In July 1997, police say Lai's Vancouver home was the target of a drive-by shooting.
But in a written response, Lai's lawyer, Peter Chapman, claimed the government relied on information from corrupt police organizations and work from journalists who engaged in sensationalism.
"With respect to the wiretap evidence, it is important to note that any assumptions made on the basis of that evidence will likely involve multiple layers of hearsay evidence."
Chapman pointed out the government's own arguments make numerous references to articles about police corruption in Macau and said the witnesses at the hearing overstated the reliability of evidence from Macau police.
He also questioned why Ottawa is trying to remove Lai so many years after he and his family became permanent residents.
Lai and his family applied to the Federal Court and the minister was ordered to complete citizenship applications for them in 2011.
"It is submitted that the minister has issued the report with respect to Mr. Lai at this particular time for the purpose of further delaying his application for Canadian Citizenship," the document states.
Chapman claimed that without a reliable foundation of compelling and credible evidence against Lai, the minister's claim can't succeed.
A ruling isn't expected from the adjudicator before August.
Documents filed in the Federal Court of Canada last March alleged that Lai laundered millions in cash in Canada.
Lai is accused of conducting 49 separate transactions worth over $2.2 million over a four-year period since he's been in Canada.
Also on HuffPost