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Nathan Jacobson is busily reassuring his business and political contacts that his reputation is intact after a long legal fight in the United States, where the controversial businessman with strong Conservative ties managed to withdraw a guilty plea to money laundering.

Launching a lawsuit against his former lawyer on Wednesday, Mr. Jacobson wants to rehabilitate his image around the world, and also repair his links with senior members of the Conservative government in Canada.

Still, with his rare mix of business ventures in developing countries, philanthropy in Jewish circles and extensive political ties in Canada and Israel – along with his dealings over the years with the Mossad, the FBI and the RCMP – he is struggling to change his image.

"I'm not a bogeyman, I'm not a corrupt person," Mr. Jacobson said in an interview as he decried his reputation as a "mystery, shadowy figure." Still, he quoted a Persian saying to explain his professional style: "You catch more fish in muddy water than you do in clear water."

Born in Winnipeg, Mr. Jacobson was an "old lefty" in his youth, according to local NDP MP Pat Martin, but he went on to develop close ties with the staunchly pro-Israel government of Stephen Harper. He has had a number of meetings with Foreign Affairs Minister John Baird, including one in Jerusalem, and other Conservative MPs, ministers and officials over the years.

Mr. Jacobson withdrew from his political circles after his legal travails became public in 2012, to avoid contaminating his friends. He now hopes that his full vindication in the U.S. will help him return to his Conservative circle, saying he did not receive any favours or government help in his quest for legal exoneration.

"Will the Conservative Party welcome me back?" he said. "If they do not want to welcome me back, it hurts no one but them."

Mr. Jacobson is now off on a trip to England, Russia and the Middle East, hoping to resume his successful business career. While his legal problems in the U.S. are over, he wants compensation for the legal troubles that followed his 2008 decision to plead guilty to a count of money laundering.

He has launched a civil suit in the Ontario Superior Court against Steven Skurka, who was his main lawyer in Canada during the ordeal. Mr. Jacobson hopes to recoup nearly $1.7-million in fees paid to Mr. Skurka since 2007, $4.5-million that he surrendered to the American government, as well as damages and other costs.

"It's not for exoneration that I'm suing Skurka. I know I did nothing wrong," Mr. Jacobson said. "This is to get compensation for a job done terribly."

Mr. Skurka, through his lawyer Brian Greenspan, denied any wrongdoing, saying there is nothing in the withdrawal of Mr. Jacobson's guilty plea that points to any misbehaviour or unprofessional practices.

"It must be remembered that once solicitor-client privilege is waived, an unrestricted opportunity is presented to contradict false and scurrilous accusations," Mr. Greenspan said of the lawsuit.

In the 2000s, one of Mr. Jacobson's companies processed payments for a pharmaceutical firm that illegally sold its products to clients in the U.S. He was indicted there in 2007 along with more than a dozen others, and he pleaded guilty in 2008 to one count of money laundering.

However, he did not show up for his sentencing. In 2012, Mr. Jacobson was arrested by Toronto police and sent back to the U.S. He quickly moved to withdraw his guilty plea by blaming Mr. Skurka for "ineffective counsel."

At a hearing into the plea withdrawal in San Diego in July, Mr. Skurka testified that Mr. Jacobson initially contemplated the possibility of entering a guilty plea on the part of his company. He added Mr. Jacobson changed his tune after learning the Americans were ready to place him on an Interpol list that could see him arrested during his international travels.

"Mr. Jacobson was a fiercely independent man, he was strong-minded, he was decisive, he was in command," Mr. Skurka said. "He never would have done this if he chose not to."

Mr. Jacobson is adamant he has always maintained his innocence, and the only reason he pleaded guilty was over the threat he faced decades in prison if he did not come to a deal with the U.S. government. He is particularly angry that his lawyers never managed to obtain disclosure of the government file against him, meaning he made his plea based on incomplete information.

"I had the life scared out of me," Mr. Jacobson said. "I was told that if I did not do it [plead guilty], I would be crushed."

Mr. Skurka's lawyer rejected allegations that any pressure was placed on Mr. Jacobson to plead guilty. Mr. Greenspan added that in his view, the U.S. government simply decided it was not worth the resources needed to pursue the case against Mr. Jacobson.

"They got to keep their $4.5-million," Mr. Greenspan noted.

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