Businessman, Harper Tory, pal of Putin, Mossad operative - the bizarre life of Nathan Jacobson

In July, 2007, Nathan Jacobson was in Damascus, walking through the marble hallways of Syrian President Bashar al-Assad’s palace, holding a collection of country music CDs. After two heavy doors swung open, the Canadian-Israeli businessman found himself facing the Syrian president.

"I heard you had arrived here, and I wanted to meet you as soon as possible,” said Assad, in perfect English. “Thank you so much for coming to Damascus."

"Mr. President, I was told that you're a fan of country music."

"Why, yes."

"Well, I brought you here this package. It's a collection of the best country music from my country."

"From Israel.”

"No, from Canada."

Jacobson had travelled to Syria to meet Assad in the hopes of negotiating a peace treaty between Israel and Syria – two countries at odds with one another for more than 70 years. The men spoke for two-and-a-half hours, trying to see if they could find common ground.

The fact that Jacobson, an obscure businessman originally from Winnipeg, had an audience with Assad reflected his close ties to Israel’s political elite and intelligence services. Indeed, he’d made the trip with the blessings of Israel’s prime minister and Mossad, its spy agency. Unfortunately, it came to naught as Syria plunged into civil war and Jacobson’s own life got terribly complicated.

Meanwhile, Jacobson’s ties to Israel’s ruling circles are proving problematic. On Wednesday, he was the subject of a report broadcast by Uvda, Israel’s leading television investigative TV program – a report National Observer contributed to – that says Jacobson made donations to important Israeli political figures, including people close to Prime Minister Benjamin Netanyahu, and to one of the country’s top rabbis. The report also said that he’s assisted Mossad in overseas operations, some of which may have been in violation of international law.

Jacobson is not new to scandal. Back in 2012, he was arrested by Toronto police after pleading guilty to a money laundering charge the U.S. Dept. of Justice had laid against him. In the years leading up to this controversy, Jacobson was a key political ally to former prime minister Stephen Harper's Conservatives. But news of his legal problems sent shock waves through Ottawa, given his ties to the Harper regime and its cabinet.

Indeed, at the pinnacle of his influence, Jacobson was a very wealthy man, a renowned philanthropist, worth “hundreds of millions” he says, with a business empire that stretched from Canada to Russia, Israel, Asia and Central America. He could get audiences with not only Netanyahu, but Russian President Vladimir Putin, the leaders of Costa Rica and Kazakhstan, and had direct access to Harper. He was friends with Jason Kenney – current leader of Alberta’s United Conservative Party – and former foreign affairs minister John Baird.

Today, his situation is very different, and his rise and fall is synonymous with the fortunes of the Conservative Party and Israel’s right-wing. When in power, the Tories courted the Jewish community, while forging an alliance with Netanyahu and his Likud party in Israel – all Jacobson’s handiwork. Today, the Tories have been relegated to opposition, Netanyahu is in deep political trouble, and Jacobson’s business empire is a shadow of its former self. And Israel, his adopted country, is mired in corruption scandals.

Winnipeg youth ends up in Israel's army and Russia

I first met Jacobson this October in the hallway of an office building in downtown Toronto as he was heading to court. Jacobson was testifying in a case involving a $32-million lawsuit he’d launched against Steven Skurka, a Toronto lawyer who’d negotiated his money laundering guilty plea with the Americans nine years ago.

Two days later, I had lunch with Jacobson at the Albany Club, an exclusive Tory private enclave located in a handsome greystone in downtown Toronto – a throwback to Upper Canada elitism. At 62, Jacobson is a heavy-set, avuncular man with broad features, wide eyes, close-cropped dark hair and the charisma of a gifted salesman. Wearing a grey shirt and dark slacks, he speaks with a rumbling baritone.

The past decade was, as Jacobson told me, “horrible.” He’s been to jail, spent a year under house arrest in a San Diego hotel and lost tens of millions of dollars. In fact, he says FINTRAC, the federal agency that monitors money laundering, is blocking his ability to bring money into Canada from Europe. Much of his troubles he lays at the feet of his former lawyer, Skurka. “If I could say he ruined my life, he did as close as could be done to ruin it,” he says.

Skurka and his lawyer declined to comment on the matter, although they are contesting Jacobson's case in court.

Jacobson was born in Winnipeg, the grandson of Jews who fled Russia after the 1917 revolution. Most of his parents’ relatives were massacred by Hitler’s Einsatzgruppen – the death squads that followed his armies east. “I had this repeated nightmare that the Nazis arrive in Winnipeg,” he says. “I'd hear the Nazis marching down the street, hear their steps and wake up terrified.”

Jacobson’s parents met in Winnipeg and had three children. “I jokingly tell people that when I was growing up in Winnipeg, that we were so poor, that if I didn't wake up in the morning with an erection I would have nothing to play with all day,” he laughs. His father was a struggling entrepreneur and Jacobson grew up in a Jewish community of social democrats. “He was a lefty in the old days,” says Pat Martin, a former NDP member of Parliament and childhood friend. “We argued about whether Phil Ochs or Bob Dylan was the best folksinger.”

In 1973, at age 18, Jacobson was hitchhiking in Israel when the Yom Kippur war broke out. He volunteered to assist the army. Like many Jewish youth of that era, he fell in love with Israel and its romantic image as a besieged, new homeland. He stayed and joined the army.

In 1981, with his father dying from cancer, Jacobson returned to Canada and eventually got a sales job with Apple, and then IBM. A few years later he started a company that helped auto parts companies improve efficiencies.

In the late ‘80s, he found himself in the Soviet Union on a business trip and realized communism was collapsing and he could profit from the post-Soviet milieu. Business deals soon followed for factory modernization. He also set up the first GM car dealership in Moscow, and imported Philip Morris cigarettes. By the late ‘90s, Jacobson was building gas stations and oil and infrastructure projects, and cutting deals with Russia’s oligarchs.

While these businesses made Jacobson rich, they also attracted unwanted attention. The manager of his GM dealership was murdered by Russian gangsters in 1994, for instance.

His Russian business ties also brought him into conflict with CSIS, Canada’s intelligence agency. In 1998, he sued CSIS for $6-million. Jacobson says a CSIS agent on the Russia desk had tried to shake him down for money (the agent promptly left the agency). The lawsuit dragged on until 2004 before it was settled. Ward Elcock, director of CSIS during this period, doesn’t recall the details of this dispute, although remarks: “Jacobson was always sort of a fantasist.”

When Putin came to power in 1999, Jacobson took a shine to the new president, whom he’s met on many occasions for social and business reasons. Putin once awarded him a gold watch. “I like Putin,” he says. “Putin brought order and he brought pride to the country.”

Powerful backer of Harper's Tories

By the 2000s, Jacobson was experiencing a political transformation. In his youth he was a leftist, protesting the Vietnam War, as an adult a Liberal and by the time Stephen Harper became Tory leader in 2004, Jacobson was a Red Tory.

Jacobson admits his biggest reason for supporting Harper was the Conservatives’ unflagging support of Israel. “It’s all about Israel and about the Middle East,” remarks Martin. “The Conservatives were so unabashed boosters and non-critical of Israel.”

Jacobson soon emerged as a key player in forging ties between Harper’s Tories, Toronto’s Jewish community – which had been drifting to the right for a generation – and Israel’s political elite. He became friends with former immigration minister Jason Kenney, who’d been tasked with cultivating the Jewish vote. “I took Jason Kenney to meet with (Netanyahu), things like that,” says Jacobson.

(Kenney, now as leader of Alberta's Conservatives, is the main opponent facing off against Premier Rachel Notley's New Democrats, leading up to the 2019 provincial election.)

Jacobson began funding and sitting on the boards of a vast network of pro-Israel charities, political lobby groups and conservative think tanks. Jacobson gave generously to the Tory party and sponsored an Israeli day on Parliament Hill. “During one of the elections, I placed ads in Jewish newspapers in Canada,” he says, citing a dozen reasons why Jewish people should vote for Harper. Thus, it was no surprise when Jacobson was photographed with Harper and Netanyahu at an Ottawa reception in 2012.

Another key top Tory cabinet minister Jacobson befriended was foreign minister John Baird. “I had meetings with John in his offices in Ottawa… multiple times,” he recalls. Once, while driving from Jerusalem with Baird, Jacobson put a call in to his old friend Pat Martin back in Canada. They got his voicemail. “It’s right in the middle of the night,” recalls Martin. “They were both drunker than shithouse rats. They were handing the phone back and forth and laughing.”

But Jacobson also was not to be trifled with, and inspires fear in some quarters. “He is not someone you cross,” says a Toronto Jewish leader, who spoke on condition of anonymity. In 2011, Jacobson sued Mark Adler, a Tory MP, seeking more than $100,000 he had given to Adler’s business, the Economic Club of Canada. Adler said the money was a gift. Jacobson said it was a loan. Adler said Jacobson threatened him, demanding to see his books. In the end, Adler paid him back.

Adler declined to comment.

Jacobson's double life - as Mossad operative

Yet no one among Jacobson’s growing network of business and social contacts knew he was leading a double life – he was helping out Mossad, Israel’s spy agency.

Jacobson became close to Meir Dagan, the head of Mossad from 2002 until 2011 (who passed away last year). Jacobson would dine with Dagan, or meet at his offices (which famously had a golden Kalashnikov once belonging to Saddam Hussein on a wall). “I remember I'd park the car on the lawn near (Dagan’s) office, not in the parking (lot),” says Jacobson. The two men traveled together, including to Greece, Austria and Armenia. He once took Kenney, then Canada’s immigration minister, to meet Dagan, who wanted Kenney to provide Canadian passports for Mossad’s overseas operations. Jacobson told Dagan this was a bad idea, and the topic never came up.

Still, Jacobson admits that it was common knowledge Mossad used Canadian passports in this way, “many times I know of.”

Jacobson was of interest to Mossad because of his international business connections. When Dagan moved to thwart Iran’s nuclear weapons program, Jacobson says he asked him to help build a network of businesspeople, including Russian oligarchs, to isolate Iran.

In 1996, Dagan had helped establish a taskforce whose goal was to stop money flowing to enemies of Israel. This became known as Tsiltsal (or, in English, “Harpoon”), a division within Mossad. One of Tsiltsal’s targets was the Beirut-based Lebanese Canadian Bank (LCB), which had an office in Montreal.

In 2011, US authorities accused the bank of laundering hundreds of millions of dollars for an international drug ring that had ties to Hezbollah. At the time, the LCB was partnering with the Royal Bank of Canada (RBC). Jacobson collaborated with Mossad to help shut down the LCB’s presence in Canada, even arranging a meeting between the head of the Harpoon unit, Udi Levi, and a senior official with RBC. Levi, according to Jacobson, scared the RBC official by saying that the LBC was “Hezbollah’s bank.”

And then there was the kidnapping of Dirar Abu Sisi, a Palestinian electrical engineer who was grabbed by Mossad while traveling on a train in the Ukraine in 2011. Sisi, a father of six, was spirited back to Israel. Sisi was detained in isolation for many days before speaking to a lawyer. He said he was tortured.

The Israelis accused Sisi of being an elite member of Hamas, helping design rockets and anti-tank missiles used in the Gaza strip targeting Israel. Sisi and his lawyers denied the allegations, saying he was not a member of Hamas, and the only evidence presented to them was his confessions, which had been obtained illegally and under torture.

In 2015, Sisi was sentenced to 21 years in prison. By then he had spent two and a half years in solitary confinement, with the Israelis refusing to put him on trial. His lawyers said this sentence was negotiated after it was apparent the Israelis were planning to give him a lengthier one.

Jacobson admits to playing a role in Sisi’s kidnapping. He says he connected Dagan with a Ukrainian oligarch he knew, Vadim Rabinowitz. “I made the introduction, because Rabinowitz was connected to the criminal world,” he says. Mossad, presumably, needed help on the ground with the kidnapping operation.

There are also questions of whether Jacobson played a role in the assassination of Mahmoud Al-Mabhouh, a top Hamas official, in a Dubai hotel in 2010. Mahboub was killed by a team of Mossad assassins in his hotel room, which was caught on videotape. However, Jacobson denies playing a role, other than saying “I know things about the affair that the man on the street doesn’t know.”

When pressed by Uvda’s host, Ilana Dayan: “(Dagan) never admitted there was a mistake there, a fault. I'm talking about the cameras…”

“Yes, I'd say so, from what I know as a person on the street, there were lots of mistakes there,” replied Jacobson.

“And you know it only as a person from the street?” asked Dayan.

“I live on the street… I know everything about Dubai. From A to Z. I have very good connections there.”

Jacobson's donations to Israel's power elite

Jacobson also began giving money to prominent Israeli politicians. When Tzachi Hanegbi, a former minister who oversaw Israel’s spy agencies, and a current a minister in Netanyahu’s government, was charged with fraud and breach of trust in 2006, Jacobson paid (US) $100,000 to help cover Hangebi’s legal bills, and later hired him a car. Hanegbi was cleared of most of the charges in 2010, although found guilty of perjury. Jacobson also donated money to a political campaign of Avi Dichter, a former head of Shin Bet, Israel’s internal security service.

Moreover, he admits giving money to Rabbi Shmuel Rabinowitz, one of Israel’s most powerful rabbis, and a civil servant who oversees one of Jerusalem's holiest sites, the Western Wall. Jacobson said the money, which totaled $20,000, was to help pay for renovating Rabinowitz’s home and cover costs for his daughter’s wedding. “So I helped him, gladly,” says Jacobson. In an interview, Jacobson seemed to suggest he gave the money to be able to gain access to the underground tunnels that connect to the wall, so he could impress his visitors (he's since denied this quid pro quo).

Yet Rabinowitz, as a public servant, is not supposed to receive such financial contributions. When contacted by Uvda, the rabbi strongly denied taking any money from Jacobson.

In 2009, Jacobson claims he paid to have a couple of Canadian election consultants flown to Israel to help Benjamin Netanyahu’s election campaign that year. Jacobson says he’s met Netanyahu more than half a dozen times. One of these consultants was Jacobson’s friend, Mark Spiro, a lobbyist and partner in a firm called Crestview Strategy in Ottawa and Toronto. Spiro says he was not paid for his volunteer work, which involved contacting voters, or knows who paid for his flight.

Then, this summer, Jacobson’s name popped out of the corruption investigation involving Netanyahu. A co-operating witness in this affair is Ari Harow, Netanyahu’s former chief of staff.

As it turns out, in 2010, when Harow was leaving Netanyahu’s office for the first time, he approached Jacobson about a job. The men met in the lobby of a Jerusalem hotel. "Ari, I don't have a position for you in my company,” said Jacobson.

“Well, look, there are a lot of things that I could do for your company?” replied Harow.

“Like what?”

“I have a lot of relationships. I can help introduce you to a lot of new opportunities through the people that I know through my network.”

Jacobson eventually agreed to pay Harow (US) $140,000 as an advance on future deals the young man would bring him. And he gave Harow a leased car. But after many months, Jacobson said not one deal transpired from this arrangement. So he asked Harow for his money and car back (the money was never returned).

Harow briefly returned to work for Netanyahu in 2014 as his chief of staff. How he sold one of his consulting firms led to an investigation against him. This past February, the police recommended Harow be indicted for bribery and fraud and other charges. Harow is now a state’s witness in two investigations against Netanyahu. So far, Jacobson has not been contacted by police about his payment to Harow.

Jacobson accused of bribery

Jacobson’s influence in Israel has raised questions about whether they allowed him to dodge a bullet with a scandal involving a company called Paygea Inc.

In 2005, Jacobson founded Paygea, which like Paypal allows people to pay on-line for various services. But Paygea needed a relationship with an established bank in order to process Mastercard and Visa payments. So he struck a deal with Israel Credit Cards Ltd. (ICC-Cal), the credit card subsidiary of the Israeli Discount Bank.

Jacobson says this deal involved giving a controlling stake in Paygea to a friend of Boaz Chechik, the then CEO of ICC-Cal. Here stories diverge about what happened next. Israeli media accounts contend that Jacobson and Chechik and the friend set up a side venture that was not approved by ICC-Cal’s board or the Bank of Israel, the country’s central bank. This side venture, which operated under ICC-Cal's nose for three years, rang up huge profits in processing credit card payments.

In 2011, the venture was investigated by the Israeli police. Eventually Chechik and his friend were indicted for accepting bribes from Jacobson and others. Paygea closed down in 2012.

Jacobson, however, says he’d been told the transfer of Paygea had been approved by ICC-Cal’s board. And that Chechik told him they planned to take ICC-Cal public. When that didn’t happen, Jacobson says he asked that control of Paygea be returned to him. But that Chechik forced him to pay his friend (US) $600,000 for this to happen.

Jacobson was never charged for issuing bribes. He did speak to Israeli police, though, about his involvement in Paygea.

Charged with money laundering and racketeering

And then there were his troubles with the American justice system.

In the early 2000s, Jacobson saw a new business opportunity – online pharmacies. As drug prices in the US spiraled upward, on-line pharmacies became popular for offering lower prices to consumers.

In Israel, Jacobson established company for people to make credit card payments called RX Payments Ltd. that catered to on-line pharmacies. In 2004, he got a new client – a well-established American on-line pharmacy later known as Affpower. Jacobson’s company processed payments for Affpower.

In August, 2007, the US Dept. of Justice announced the indictment of 18 people associated with Affpower – including Jacobson (who was listed as the 18^th). They alleged this network had generated (US) $126-million in illegal sales of prescription drugs.

The indictment said Affpower sold drugs to patients who did not have prescriptions issued by their own doctors. And that Affpower’s doctors conducted no physical or mental examinations before issuing prescriptions, had no contact with customers, and had no physician-patient relationship with any customers.

Jacobson was cited for money laundering, racketeering, conspiracy to distribute controlled substances, wire and mail fraud, and other charges. Jacobson says he was “shocked as shit” for being named in the indictment.

For one thing, Jacobson had cut ties to Affpower the previous year, worried about its operation. Moreover, when Jacobson entered the on-line pharmacy sector, he’d obtained opinions from Canadian and American lawyers on the legality of RX’s operation. While the letters gave diverging opinions, they said if RX followed certain procedures, it was within the law. As well, Jacobson says he received a letter from Affpower’s lawyer vouching for its business. Jacobson says he also went to the lawyer for the Canadian International Pharmacy Association (CIPA) to provide an analysis, and adopted their standards.

And he got terms of service between the two companies saying they would not process any illegal payments

Finally, in February, 2007, Jacobson and his employees met with the Drug Enforcement Administration (DEA), handing over their lawyers’ letters and client files offering to help the agency weed out bad actors in the on-line pharmacy industry. “My people were helping (the DEA),” says Jacobson. “That's not (the actions of) a person that's guilty.”

Jacobson pleads guilty — to his regret

To handle his defence, Jacobson hired prominent Toronto criminal lawyer Steven Skurka. Due to the fact he was not licensed to practice in the U.S., Skurka brought in two American lawyers to advise him on the case — who reported directly to Skurka, and not to Jacobson.

Jacobson’s lawyers faced a problem: as long as he remained out of U.S. custody, the Americans would not hand over full disclosure of their evidence against him. Meanwhile, Jacobson repeatedly professed his innocence.

Skurka began holding meetings with U.S. Dept. of Justice officials, who fed Skurka morsels of their evidence against Jacobson. By January of 2008, the Americans were pressuring Skurka to get Jacobson to agree to a plea deal, saying they were “ready to rock and roll” on his client.

Skurka and Jacobson’s stories diverge here. Skurka said Jacobson was told his case was defensible if he fought it out in the United States, but that Jacobson insisted on pleading guilty and striking a deal.

Jacobson, on the other hand, says Skurka pressured him to sign the plea agreement – telling him he would be found guilty and face a lengthy prison sentence if he didn’t otherwise.

In the end, in May, 2008, Jacobson signed a plea agreement to one money laundering charge and agreed to pay a US $4.5-million fine. In return, the agreement would be sealed and Jacobson would provide the Americans with information on illegal e-commerce and on-line pharmacy operations. The hope was if he cooperated sufficiently, his charge would be reduced to a misdemeanor and he would avoid prison, or at least receive a minimal sentence.

In total, Jacobson ended up paying Skurka $1.7-million, of which Skurka pocketed a little more than $1-million (the rest was paid to other lawyers or for expenses).

For the next four years, Jacobson’s plea agreement was a closely-guarded secret, as he continued to pursue his business and political interests, hobnobbing with prominent Tories and other leaders, and assisting Mossad. He held clandestine meetings with various American government agencies, in places like the Bahamas, giving them information – such as evidence an Israeli bank had ties to organized crime.

Jacobson scandal breaks

But, in time, Jacobson said he realized he had made a terrible mistake.

For one thing, the other defendants in the Affpower indictment were walking away with light punishments – defendants much more centrally involved with the company. In 2009, a mistrial occured in the case of seven of the defendants, before their lawyers accused prosecutors of withholding evidence. In the end, none of them were sentenced to prison. Moreover, one of the key witnesses against Jacobson had fallen under a cloud after lying to prosecutors about a financial matter.

Jacobson became disillusioned with Skurka and dropped him. By 2012, the Americans were also clearly unhappy with what Jacobson was providing them: that summer they ordered him to travel to San Diego to face a sentencing hearing. “Based on the sentencing guidelines then in effect, and the amount of money that Nathan was alleged to have laundered – emphasis on alleged – he would have been looking at significant (prison) time,” says Michael Attanasio, a San Diego-based lawyer who Jacobson later hired to have his guilty plea overturned. “I mean five years and up” – or the worst punishment of anyone involved in the Affpower matter.

Jacobson failed to appear for the hearing. He was on business in Myanmar at the time, and says there was a mix up with a court official who failed to inform the judge he couldn’t show up. Thus, the US government issued a warrant for his arrest. Jacobson immediately returned to Toronto. That October, the Americans issued an extradition order – and all hell broke loose.

Liberal opposition MPs quickly seized on Jacobson’s ties to Harper. “The government cannot wait to rush two poor Nigerian foreign students out of the country, but their Conservative buddy walks around with impunity,” one opposition MP said in the House of Commons.

On the morning of his arrest, 14 heavily-armed Toronto police officers arrived at Jacobson’s midtown condo. He spent a long weekend in a detention centre before being released on bail.

Given that no one knew Jacobson had pled guilty to money laundering four years earlier, this news immediately made him radioactive to the Tories and friends in the Jewish community. Even today, five years later, only close friends agreed to talk to the National Observer about him. “(The Tories) dropped him like a hot potato, which I thought was kind of shitty of them,” says Pat Martin, who stood by Jacobson.

In 2013, Jacobson flew to San Diego and gave himself up, spending 45 days in prison (one of his cellmates was the nephew of Mexican drug cartel boss Juan “El Chapo” Guzman). After friends raised (US) $1.4-million to pay for a bond, he was released and moved into the luxury Sofia hotel in downtown San Diego, with an ankle bracelet on his leg. There, Jacobson would spend more than a year awaiting his fate.

Guilty plea is thrown out

Jacobson hired Attanasio, a talented California litigator, to determine his options. Attanasio faced a daunting task: getting a guilty plea vacated is extremely difficult.

But as he began examining Jacobson’s case, Attanasio became convinced his client was innocent of any crime and should never had pled guilty in 2008 - and that, ultimately, Jacobson received poor legal advice from Skurka. Attanasio submitted a motion to withdraw Jacobson’s guilty plea on the grounds he had gotten “ineffective assistance of counsel" and asking for a trial on the original money laundering charge.

The motion was heard in the summer of 2014 at San Diego’s main courthouse. The only person to testify was Skurka. During the hearing, it was revealed that the two veteran American lawyers Skurka had hired to assist him had serious misgivings with the plea agreement – including whether enough evidence had been provided by the government to establish Jacobson’s guilt. One of them had such vocal reservations Skurka fired him. The other wrote a strong memo in which she raised numerous issues with a draft of the agreement – although she later endorsed the deal. (Jacobson claims these concerns by the American lawyers were never passed on to him.)

On the fourth day of the hearing, the lawyer for the US government said he needed to go to the hospital to attend to a health problem. The hearing was postponed – and never resumed.

That September, the US government withdrew Jacobson’s guilty plea and dismissed all of the counts in the indictment against him (although the government kept the $4.5-million fine Jacobson had paid). The judge noted in her order that “based on the evidence before this Court, including Mr. Jacobson’s sworn declaration and the testimony of his former counsel Steven Skurka… the Court finds there are fair and just reasons for withdrawal of Mr. Jacobson’s guilty plea.”

Jacobson was now a free man. The toll on him, says his cousin and Winnipeg developer Hart Mallin, was considerable: He had lost businesses and his reputation, and done damage to his marriage. He and his wife Lindi had adopted an orphaned baby from Ukraine in 2001 and Jacobson spent more than a year away from his family. “This was a bizarre situation,” says Mallin. “This was an odyssey from being in control of one’s life and back again. Does one change from that?”

But Jacobson was also hopping mad. He promptly sued Skurka for $32-million. Says Jacobson: “He took a person that was wealthy, that was a community leader, that was active politically, whose name would open doors, who saw things as only getting better in life, and misrepresented me.”

Skurka and his lawyer declined to comment on the matter since it's before the courts.

Today, it’s unclear how much Jacobson will get drawn into Israel’s political scandals. But in one respect, his life story reflects how the romantic Israel of his youth has disappeared. “The mentality of the country has very much changed,” admits Jacobson. “Corruption’s become more predominant.” Meanwhile, he is struggling to sort out his own legacy. “I am a true enigma,” he tells me. “How do I end up in these places? And how do I end up close to all these people? How did Jacobson go from River Heights in Winnipeg to the office of the president of Russia or the prime minister of Israel or the president of Syria?”