Malkin first applied for permanent residency as an entrepreneur with the Canadian consulate in Detroit, Michigan, in 1994, and filed a complaint in 1998 after the request was denied, the records on the court's web site show.
The epic battle has dragged on ever since, with Malkin getting perhaps his first break last week when the court in Toronto ordered a review of the case after Canadian immigration authorities conceded that Malkin had been denied procedural fairness.
Malkin's name is spelled Vitali Malkine in the court records, but both their content and e-mailed comments by court spokesman Andrew Baumberg leave no doubt that Malkine and Malkin are the same person.
The court documents show that Canadian authorities used Malkin's controversial past in the turbulent 1990s as the reason to deny him residency.
A visa officer told the court that Malkin was a shareholder in a company thought to have received money diverted from a debt-reduction deal with Angola. "Mr. Malkine is reported to have personally received some $48 million in the transaction," a passage published by the court in May reads.
The visa officer also noted Malkin's association with individuals involved in money laundering, arms trade and trade in Angolan "conflict diamonds," the documents say.
Malkin's involvement in President Boris "Yeltsin's re-election campaign is also discussed, with the officer stating that Mr. Malkine had used profits from organized crime to subvert the democratic process in Russia," they say.
Malkin has vehemently denied the charges and complained that they might hurt his reputation as a senator, according to the documents.
Repeated attempts to reach Malkin, 56, for comment were unsuccessful on Thursday, Friday and Monday. He did not reply to questions sent by e-mail, and a woman who picked up the phone at his Federation Council office said he would be away for the rest of the week. Malkin's lawyer in Toronto, Robert Young, did not respond to written questions.
Malkin was an influential banker in the 1990s, serving as president of Rossiisky Kredit bank and co-owner of Impexbank. He was said to be close to Yeltsin. In 2006, he and his partner Boris Ivanishvili sold Impexbank for $550 million to Austria's Raiffeisen Bank.
Last year, he was ranked by Forbes magazine as the country's 85th-richest man, with an estimated wealth of $1 billion.
Malkin has represented the east Siberian republic of Buryatia in the Federation Council since 2004.
The allegations in the Canadian court documents closely resemble reports that surfaced in the wake of a money-laundering case involving Malkin in Switzerland in 2002.
The case was dropped two years later, but Global Witness, a London-based NGO that investigates corruption in the natural resources sector, said it had information that bank transfers of debt repayments from Angola to Russia ended up in private accounts, including Malkin's.
Global Witness and Swiss advocacy group Aktion Finanzplatz Schweiz have called for the affair, dubbed Angolagate, to be reheard by courts but so far with little success.
The two advocacy groups said more than $770 million in Angolan oil revenues were paid into a Swiss bank account belonging to Abalone Investment Limited, a shell company run by businessman Pierre Falcone and his associate, Russian-Israeli billionaire Arkady Gaidamak.
The Russian Finance Ministry received only $161.9 million, while the rest was transferred to accounts belonging to Angolan officials, a French arms broker and Malkin, the advocacy groups said. They said $48.8 million was transferred to an account belonging to Malkin and $60.5 million was transferred to an account belonging to Gaidamak.
The Swiss paper Le Temps reported in 2002 that Malkin was a shareholder in Abalone and that the Angolan debt deal might have been used to finance Yeltsin's re-election campaign in 1996.
Malkin and Gaidamak have denied the allegations.
It was unclear why Malkin would wage such a prolonged battle to enter Canada. The Canadian National Post newspaper, which broke the story last week, reported that he owns 111 condominium units in Toronto.
By 2007, Malkin had given up on moving to Canada and applied for a visitor's visa to look after his property, the newspaper said, citing no one.
Court records from 1999 say Malkin presented evidence of property purchases in Ontario by a company he headed. Yet immigration authorities decided that this does "not indicate that Mr. Malkine has been actively involved in business in Canada or that he has the intention and ability to provide active and on-going participation in the management of a business or commercial venture," it said.
Israeli newspaper Haaretz reported in 2007 that Malkin's son had lived in Canada with his mother since 1989. Leonid Malkin immigrated to Israel in 2005 and changed his name to Ilan, the report said.
Ilan Malkin did not return calls to a Tel Aviv luxury restaurant that he co-owns.
A Canadian Embassy spokesman declined to comment on the Malkin visa issue.
Malkin is not the first prominent Russian to be denied entry by Western countries. The U.S. State Department for several years refused to give a visa to metals tycoon Oleg Deripaska over concerns about his possible links to organized crime.
Crooner-turned-lawmaker Iosif Kobzon was denied a U.S. visa 1995 because of FBI reports of ties to organized crime.
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