Nathan Jacobson, a former Conservative Party fundraiser who has claimed friendships with Canadian cabinet ministers, is getting bail again in a precedent-setting case for someone who has pleaded guilty to a crime.

The saga of Jacobson, 59, a Winnipeg-born businessman who made millions in Russia after the fall of the Soviet Union, continued in San Diego, Calif., Friday, where U.S. government prosecutors called him a bail jumper, an obstructer of justice and a liar as they asked a U.S. judge for a minimum of $5 million in bail.

Jacobson is "asking this court to issue the first such ruling in the nation," said the government’s bail status report, a document stating its case against the granting of bail. "The United States has found no cases in which a defendant who failed to appear and had to be extradited to the United States was subsequently granted bail pending trial or sentencing."

But a U.S. judge did just that this week.

Jacobson's bail was set at $1.4 million US on Friday. As of late Friday evening, it was unclear when Jacobson would be released.

The Canadian defendant is also seeking to retract his guilty plea and arrange for a new trial. That hearing is set for November 15, but if his motion is rejected he will be sentenced December 13.

Jacobson's troubles began six years ago when he was indicted in the U.S. for helping Affpower, an illegal online drug distribution network, process $126 million in credit card transactions through his company, RX Payments.

In the spring of 2008, after being charged with 10 counts, ranging from racketeering to conspiracy to commit wire fraud, Jacobson pleaded guilty to one count of conspiracy to commit money laundering, which carries a maximum sentence of 20 years.

As part of his plea agreement, he agreed to hand over his $4.5 million in profits from the scheme, and because he was willing to co-operate with authorities, he was allowed the freedom to remain out of custody and travel outside the country while awaiting sentencing.

Posed with politicians

During that time, he helped in the Tories' 2008 federal election campaign, was pictured in a photo with Prime Minister Stephen Harper and Israeli Prime Minister Benjamin Netanyahu, and claimed friendships with ministers John Baird and Jason Kenney.

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Nathan Jacobson is pictured with Prime Minister Stephen Harper, left, and Israeli Prime Minister Benjamin Netanyahu. Harper has said this is the only time he met Jacobson. (PMO photo)

Those politicians have since told the media they were not aware of Jacobson’s legal issues, and Harper’s spokesman said the photo was the only time he met Jacobson.

Prior to his arrest, Jacobson was also quick to show a cellphone photo of himself with Syria's president Bashar Al-Assad in what looks to be Al-Assad’s office.

"I was trying to negotiate peace," Jacobson told a CBC News producer during one of his interviews in the fall of 2012.

When his co-operation with police waned, U.S. authorities scheduled a sentencing hearing in the summer of 2012 in San Diego. Leading up to that date, according to a government status report submitted in court this week, Jacobson "lied to the probation officers.

"His false and misleading statements included that: (1) there was an ongoing criminal investigation of his Canadian lawyer and another of his lawyer-business counselors; (2) there was reasonable evidence to believe that his lawyer 'conspired with the U.S. prosecutor … in order to falsely obtain a guilty plea' from him; (3) evidence existed that $1 million that he forfeited was illegally paid into a 'whistleblower' account; and (4) his legal files were sold by his attorney to Ukrainian organized crime members," according to the report filed this week.

Arrest in Toronto

When Jacobson missed that 2012 sentencing hearing, a San Diego judge issued an arrest warrant, which the RCMP failed to act on, much to the chagrin of the San Diego prosecutors.

An RCMP spokesman told CBC News at the time that the Mounties were not obligated to act on the July 30, 2012 warrant, and said it was up to local jurisdictions to execute it. The Ontario Provincial Police had the so-called red notice certified by a Toronto judge and finally, on October 25 of last year, the Toronto Police Services fugitive squad went to his Spadina Road condo and arrested him.

Within a week, he was granted bail in a Toronto court. The move was not contested by a federal prosecutor, who told CBC News he had conferred with the federal attorney general's office about the decision.

Jacobson remained free in Canada until June 27 of this year when he handed himself over to Canadian authorities, who escorted him to a plane bound for San Diego. Until Friday, he has been in the Metropolitan Correctional Center in San Diego.

His bail from that institution has been granted on condition he provide a personal assurance bond of $1.4 million, that he remain in San Diego County and submit to electronic monitoring.

Report raises flight risk

In his bail status report this week, U.S. assistant district attorney Phil Halpern lays out his fears that Jacobson will not return.

"It has been conclusively established that Jacobson will not appear if he feels it is not in his best interests," Halpern wrote, adding that Jacobson faces a significant sentence and has a means to flee.

"He is a dual citizen of Canada and Israel, with homes in both countries, and previously served with Israeli Special Forces," Halpern's report says. "By his own admission, he has extensive business and personal contacts throughout the world, including Israel, Russia, Costa Rica, Myanmar and Ukraine. Jacobson has also made it clear that he has ties to elements of organized crime in both Israel and Russia."

The report adds that he was a multi-millionaire in recent years, with assets located in different countries, but "most disturbingly," says the U.S. government status report, "it would not be surprising, if Canada failed to extradite him a second time if we let him loose."

In a subsequent hearing Friday, a judge and counsel agreed to exchange motions and have a hearing on November 15

If you have tips on this story, contact john.nicol@cbc.ca.