The Supreme Court in Canada has refused a plea for refugee status by a man described by the Chinese government as its most wanted fugitive.
Lawyers for Lai Changxing say he fears torture if he returns to China
Lai Changxing, who has been fighting to stay in Canada for the past six years, is accused of running a multi-billion dollar smuggling ring in the 1990s.
He has lost repeated bids for refugee status for himself and his family.
The Canadian immigration board will now decide whether to deport Mr Lai, who argues he faces persecution in China.
Canada's Department of Citizenship and Immigration has previously argued he is a common criminal rather than a political refugee.
'Death or torture'
Mr Lai arrived in Vancouver with his wife and three children in 1999 after fleeing China.
Chinese authorities accuse Mr Lai of being behind a network that smuggled billions of dollars worth of goods into China from Hong Kong, protected by corrupt officials.
His lawyer, David Matas, told the AFP news agency the Lais were "disappointed" by the Supreme Court ruling.
Mr Matas had argued Mr Lai feared death or torture if he was deported to China, while his wife could be treated inhumanely.
Several people connected to the case have already been executed in China, and others jailed.
Mr Matas said he planned to petition the UN Committee against Torture on Mr Lai's behalf.
Beijing has made a promise in a diplomatic note to Canada that Mr Lai would not be sentenced to death if he is found guilty of a criminal charge.