Lai Tong Sang was ordered deported by an Immigration and Refugee Board adjudicator last August, on the grounds that he was criminally inadmissible to Canada.
Lai, 59, quickly filed the application for a judicial review by the Federal Court.
Following a hearing last month, Justice Roger T. Hughes found there was "a wealth of evidence" linking Lai to the triad and its illegal activities. He dismissed the application.
"The (board) member had abundant evidence in the record, including a book and an article directly implicating the applicant as a prominent triad member," Hughes wrote in his March 17 decision.
There was evidence that such triads were involved in illegal activities, Hughes said, and evidence directly named Lai as a principal member — an allegation he did not counter with any material evidence.
"With such a wealth of evidence against the applicant and virtually nothing to support his position, the result was not only predictable, but inevitable," Hughes wrote in his decision.
"I see no point in quashing the decision and sending it back."
The Immigration and Refugee Board heard Lai was the "dragon head" of the Shui Fung, or Water Room, gang. He arrived in Canada on a permanent resident visa in October 1996, in the midst of a bloody turf war over control of Macau's criminal underworld.
Lai had his wife and three children in tow and they, too, faced an admissibility hearing last year. The board adjudicator found they are admissible and may remain in Canada.
The arrival of Macau's notorious gang boss in Canada made headlines and prompted a federal review of the immigration office that approved his application.
He survived an assassination attempt at his Vancouver home in July 1997 but immigration officials waited over a decade for access to police wiretap information that allowed them to move to have Lai deported. It wasn't until July 2011 that immigration officials had the necessary information on Lai's criminal ties.
In the mean time, documents filed with the Federal Court in an earlier application alleged Lai laundered millions of dollars in Canada.
Citizenship and Immigration produced a report from FINTRAC — Canada's financial intelligence agency — saying that from Oct. 15, 2002 to Nov. 8, 2006, investigators tracked 49 separate electronic funds transfers amounting to more than $2 million.
Hughes said the immigration board member reached "a reasonable conclusion" that Lai was a member of the triad.
"A review of the record ... shows abundant evidence that triads in Macau were engaged in a number of activities that any civilized country would find to be illegal and indictable; including cold-blooded murder in public, extortion, assault, and more," Hughes wrote.
Whether Lai must actually be deported is unclear. He was not in Canada for his hearing last summer but, rather, called in from Macau.