Whatever the relationship between Prime Minister Stephen Harper and Nathan Jacobson, the high-flying Canadian businessman now a fugitive from U.S. justice, one thing is certain: they certainly didn’t just run into each other at a “community event” as the PMO claims.

Jacobson had an intimate relationship with several senior Harper cabinet ministers, paid off a CSIS agent while doing business in Russia, and apparently finessed a secret settlement out of the Canadian government under the Liberal administration of Jean Chretien even though the government denied ruining Jacobson’s business interests abroad.

Notwithstanding the Harper PMO’s ludicrous official line that “the prime minister may have met with Mr. Jacobson at a community event, as he meets thousands of Canadians from all walks of life each year,” perhaps they would be good enough explain this: who is the man standing between the prime ministers of Canada and Israel and how did he make his way into the inner sanctums of the current government?

For a prime minister who has lived through the murky departure of Arthur Porter, his handpicked chair of the Security and Intelligence Review Committee, and who also hired convicted felon Bruce Carson as a senior policy analyst and troubleshooter, it is a momentous question.

Porter left office under a cloud after his dealings in Africa with an arms dealer were revealed, and now faces a police investigation from his days at the McGill Hospital Health Centre and a billion-dollar contract the hospital awarded to disgraced Canadian engineering firm SNC Lavalin Group Inc.

Carson was a lawyer who had been jailed and disbarred for multiple counts of fraud, a criminal past that, according to his own lawyer, was fully disclosed to the government during a security check before joining the inner circle of the PM’s staff.

And so, to Nathan Jacobson: For a man with a devastating secret, the Winnipeg-born businessman lived like a male version of Cinderella – until the legal clock struck midnight.

He was rich, powerful, funny, generous, and very well-connected. The Jewish community never had a more dedicated son. Well known for his philanthropy, Jacobson and his wife Lindi were staunch backers of Israel. After high school in Winnipeg, Jacobson spent six years in the Israeli Defense Forces.

The couple were major sponsors of an event in September 2007 to celebrate the 40th anniversary of the “re-unification of Jerusalem.” Jacobson was also a sponsor of the Maccabi Tel Aviv football club, a franchise that Gerald Schwartz of Onex Corporation once considered buying. (It was ultimately acquired by two Russian oligarchs in December 2007. Ironically, they were associated with the Russian defence corporation Rosoboronexport, Syria’s top weapons supplier.)

In October, 2010, when the Royal Winnipeg Ballet celebrated its 70th anniversary with performances in Israel, two of the major funders of the tour were Gerald Schwartz and Nathan Jacobson.

Even Jacobson’s anonymous philanthropy sometimes drew attention. A visitor to his ancestral home, Pavolitch in western Ukraine, admired how the Jewish cemetery there had been restored and noted the local talk about the modest benefactor whose name doesn’t appear at the site. “The renovations were done there a couple of years ago by a guy named Nathan Jacobson…”

The blogger posted photos of the restored graveyard on the internet. On the chain-link fence around the burial ground was a sign that read, “The cemetery is renovated by descendants of the Jews buried here, in their blessed memory.” The blogger got this response from a native son of Winnipeg who knew Jacobson from childhood days: “He’s about 10 years older than me and grew up around the corner … Nathan is an apparently successful international-man-of-mystery kind of guy.”

Not badly said.

Jacobson’s business acumen and philanthropy made him legendary in both Canada and Israel. He was honoured at the 38th Annual Sports dinner in Winnipeg on June 23, 2010. “Nathan lives in Herzylia, Israel and is the current International Ambassador of Jerusalem,” a local paper gushed. Eleven hundred people attended the event, including the Israeli ambassador who flew in to the evening.

There were glowing profiles in the Winnipeg Jewish Review, a favorable notice in the Jewish National Fund of Canada newsletter, and praise in newspapers like the Jerusalem Post and Haaretz for his entrepreneurial brilliance.

Jacobson was busy in the world of the boardroom too, holding positions on the Jewish National Fund, Meir Hospital and the Ukrainian Jewish Congress. He also sat on the Board of Tel Aviv University and personally funded two faculty recruitment chairs at TAU, bringing over young researchers from Toronto. One of his fellow board members was Sheldon Adelson, a casino magnate and, according to Forbes, the 12th richest person in America.

The two men shared the same working-class roots as descendants of immigrants from the Ukraine and both were self-made tycoons. The businessmen have given generously to a variety of charitable causes and shown unwavering loyalty to the staunch right-wing policies of Israeli prime minister Benjamin Netanyahu — and to neo-conservative causes in their own countries.

Adelson, for example, has worked ceaselessly to have convicted spy Jonathan Pollard released from a U.S. prison, lobbied Washington to move its embassy from Tel Aviv to Jerusalem, and championed former GOP presidential contender Newt Gingrich after he declared the Palestinians to be an “invented people.”

In the current U.S. election, Adelson has promised “limitless” funding to defeat the Democrats. He may be the only political donor in history to have given $10 million to political activists who also happen to be billionaires themselves. Charles and David Koch, the recipients of the contribution, and whose own companies have annual revenues of $100 billion and estimated personal net worths of more than $30 billion each, have dedicated the donation to taking down Barack Obama through their action committee, Americans for Prosperity.

If Romney and the GOP couldn’t imagine a better supporter than Sheldon Adelson, Stephen Harper and the Conservative Party would have trouble finding a more dedicated backer than Nathan Jacobson.

Jacobson not only shared their conservative ideology, but put his money where his political heart was; from 2007 to 2011, he made the maximum donation to the party, and also gave to several individual Conservative riding associations.

The love did not go unrequited. Jacobson was a fixture at major events involving senior Harper cabinet ministers.