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An 88-year-old accused war criminal has once again been stripped of his Canadian citizenship, following the latest initiative to deport him that was quietly spearheaded by Immigration Minister Jason Kenney.

Court filings show the Conservative government signed an order in-council on Sept. 27, 2012, reaffirming the government's right to strip Helmut Oberlander of his citizenship and send him back to Europe.

This is the latest in a string of efforts to kick out the Ukrainian Canadian from Canada for complicity in war crimes. The Waterloo resident has long upheld he never killed anyone during the time he served the Nazis as a conscripted translator. He first got his Canadian citizenship in 1960, and has been fighting the government's efforts to remove him since the mid-1990s.

Since 2009, the Oberlander case has been in legal limbo, when the Federal Court of Appeal ruled 2-1 that, before the government removed Mr. Oberlander, it first had to first consider whether he was forced to join the German armed forces under "duress."

While legal questions about his procedural rights have frequently arisen, there is no debate that Mr. Oberlander was once affiliated with a group that committed atrocities – a "mobile civilian-killing squad" in Ukraine that was known as Einsatzkommando 10a.

"The five EK units of Einsatzgruppen D, to which EK 10a belonged, executed 55,000 civilians between June, 1941, and mid-December, 1941, and another 46,000 by April, 1942, and many more there after," ruled a Canadian judge in 2008. "By August, 1942, EK 10a had executed so many thousands of Jews that its operational area was declared Judenrein (Jew-free)."

Whoever wins or loses the latest case, it could well be Ottawa's last chance to remove Mr. Oberlander. This past weekend an 88-year-old accused former Nazi concentration-camp guard died near Pittsburgh, having long resisted the U.S. government's efforts to deport him.

"This case is a touchstone case for Canada on Nazi criminals. The window of opportunity is basically closed," says Bernie Farber, a former executive director of the Canadian Jewish Congress, who has followed the Oberlander case for 20 years. "There are no more alleged Nazi war criminals to hunt down or go after, so this one is important."

"It's time – this has gone on way too long," he added.

In response to the cabinet's September order to strip him of his citizenship, Mr. Oberlander launched a renewed legal bid last month to stay in Canada, alleging that the cabinet "breached the principles of fairness required by law."

The new Federal Court filings include a 2010 affidavit, where Mr. Oberlander descries how he was a teenaged Ukrainian of German heritage, and "caught between the brutal worlds of Stalin and Hitler" as he was conscripted.

"I was a young boy, living in fear, doing what I was told. I believed I had no choice. I had absolutely no authority and I was the youngest person in the unit," Mr. Oberlander writes in his affidavit. "While I was with the German armed forces I did not kill or hurt anyone."

He says that "I am and have always been considered by others to be a valuable Canadian citizen and an asset to my country … I ask that I am able to live the remainder of my life in Canada without the threat of losing my citizenship again."

Mr. Kenney, the Immigration Minister, has rejected such arguments. In a brief he submitted to his cabinet colleagues, he says Mr. Oberlander "served the members and the purposes of this killing squad with knowledge of the atrocities it carried out."

The minister's report argues that Mr. Oberlander never deserted the German armed forces even though he had had chances to: "In Mr. Oberlander's case there is no evidence of an imminent threat of harm over the at least one year and a half period where he served the Ek10a and the years after that when he remained in various capacities with the Nazi regime."

Ultimately, "Mr. Oberlander has not demonstrated that he meets any of the three conditions to satisfy the defence of duress," the report says.

It is unclear how quickly the Canadian government could act to remove Mr. Oberlander. Lawyers acting for him did not have any immediate comments when contacted Thursday.

"We will revoke citizenship from individuals who obtain it fraudulently to ensure that Canada is not a safe haven for fraudsters and criminals," said Alexis Pavlich, a spokeswoman for Mr. Kenney, in an emailed statement.

However, one of Mr. Oberlander's daughters says that the federal government is being "heartless" by continuing to pursue the case.

"They have no new evidence, they have nothing new. They are being heartless," said Irene Rooney who recently saw her father on Christmas Day. "… There has been a lot of trials and tribulations and unjust allegations. It's enough now – what the government is putting him through is absolutely ridiculous."

Mr. Farber, the former Canadian Jewish Congress official, says that he hopes the deportation occurs sooner than later.

"It matters not if he was a translator or a cook – they were all part of the pirate ship and they helped oil the wheels of genocide," Mr. Farber said. "He would never have been admitted to Canada if he had made an admission that he was involved."

He added that "We have to give the government full marks for its tenacity in this case. This is the type of thing an immigration minister should be doing."

Editor's note: An earlier version of this story referred to Helmut Oberlander as an accused Nazi war criminal. While Mr. Oberlander admits to serving with the "German armed forces" during the Second World War, he says he never subscribed to the Nazi ideology.

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