Obama's man in Ottawa

David Jacobson is a former litigator with a soft spot for cigars

Obama’s man in OttawaBarack Obama’s new ambassador to Canada, who has arrived in the midst of tensions over trade, energy and the border, has a reputation for embodying the “no drama” rule that was emblematic of the Obama campaign. In the course of 30 years as a corporate litigator with a single Chicago firm, David Jacobson was known for never losing his temper, not even raising his voice. “David is an extraordinarily pragmatic individual,” says John Grossbart, a colleague who has been in tough spots with Jacobson on high-stakes cases. “He never loses his cool.” So it was an odd sight when his wife, Julie, an elegant brunette and fellow law school grad, walked in on him one day eight years ago, after the hard-fought 2000 presidential campaign that pitted George W. Bush against Al Gore, and caught him throwing newspapers at the wall.

“I am one of these guys who is addicted to cable television. I read newspapers religiously and voraciously,” says Jacobson, 57, who still seems a bit surprised to find himself and his wife on the pale yellow sofa in the stately official residence in Ottawa’s leafy Rockcliffe Park, hours after presenting his diplomatic credentials to Governor General Michaëlle Jean, enjoying a cordial private meeting with Stephen Harper, and emerging unscathed from his first Canadian media scrum. “I would get madder and madder and fling newspapers around the room, and yell and scream at the TV,” he continues, describing his reaction to the election results. “One day, Julie, who is much smarter than me, said to me, why don’t you try and do something?”

He took his wife’s advice. That “galvanizing moment” transformed the former political science major—who’d once worked on the presidential campaign of moderate Republican candidate Howard Baker—from a “dabbler” in politics into a fundraiser for national Democratic candidates. And one of such doggedness and networking talent that he eventually became the number two money man in the leviathan operation that financed Obama’s stunning ascent to the White House—and shattered records for getting people to fork over money to a politician. As the former deputy finance chair of the Obama campaign, Jacobson does not apologize for his role as what some people call a “bagman.” “One thing I learned quickly in politics is that they don’t need very many people to do politics, or to write speeches, or to do research,” he says. “But they need a lot of people to raise money. It’s the one thing ordinary people could do.”

Having just arrived in the Canadian capital, Jacobson knows he has to settle into the job and speaks only in broad strokes about what he hopes to accomplish. But the first thing everyone in Ottawa wants to know about a new U.S. ambassador is: how well does he know the president and can he get him on the phone? Jacobson says he first met Obama, then an Illinois state senator, sometime in late 1999 or 2000, introduced over lunch by a mutual friend he declined to name. “He was exceedingly impressive,” he recalls. Jacobson supported Obama in his campaign for the U.S. Senate. In the early primaries for the last presidential campaign, he supported Joe Biden, now the vice-president, but switched his allegiance as soon as Obama entered the race. The Obama camp reported that Jacobson personally raised between $50,000 and $100,000 for the campaign—a significant amount, but hardly in the top tier of Obama “bundlers”—fundraisers who tap extensive personal and professional networks for individual donations. Asked about the figure, Jacobson explains simply, “I was not particularly concerned with credit.” His job, as the deputy finance chairman (a volunteer position)—the number two in a committee of 500 people—was to organize and coordinate large fundraising functions.

He describes his personal relationship with Obama this way: “Are we friends? Are we buddies? I’m not so sure. I think we are friendly. If I had to talk to him about something serious I am confident that I could get him on the line. But you should understand that it should be something very serious before someone picks up the phone and says, ‘I need to talk to the President.’ ”

After Obama’s inauguration, Jacobson worked in the White House as special assistant to the President in the office of presidential personnel—which staffs the roughly 4,000 so-called political appointments who serve at the pleasure of the President, from the secretary of state down to press aides. “We would find appropriate people for the positions and make recommendations to the President, and he would say yea or nay.” His White House sojourn was longer than expected, since the Senate took its time confirming Obama’s appointees, including ambassadors. The silver lining was that while he waited for his own confirmation as ambassador, Jacobson spent many months seeing how the White House works from the inside. “There are a large number of people in the White House, very senior people, who I also know very, very well,” he says. “Some from the campaign, some from before the campaign, who I could pick up the phone and call, seek their advice, seek their guidance, seek their counsel, provide a message from a Canadian government official, what have you.” Likewise, Jacobson, who also worked on Democratic Senate campaigns, has made lasting contacts on Capitol Hill—where many cross-border irritants fester.

While Bush came under harsh criticism for appointing top campaign donors to top government jobs across the government, Obama has done better, according to Craig Holman, a congressional lobbyist for the watchdog group Public Citizen. Better, that is, with the notable exception of ambassadorships, where donors continue to get plum postings. Obama’s choice for the U.K., lawyer and investment banker Louis Susman, was nicknamed the “Vacuum Cleaner” because of his skill sucking up cheques for Democratic candidates. Northern Virginia car dealer Donald Beyer, who raised half a million dollars for Obama, is headed to Switzerland. “It is disappointing to see the administration operating that way when it comes to ambassadorships,” says Holman. As for Jacobson, he said, “I’m not criticizing the person. He may be a fine guy. But he’s getting this position because he’s a fundraiser, and that I find reprehensible.”

Jacobson, who during a 30-year legal career has dealt with complex commercial litigation, mergers and acquisitions and cutting-edge securities law, with clients ranging from Allstate insurance to General Motors, rejects the critique. “I would like to think I was selected because of my qualifications to do this—my background and my commitment to the values and policies of the Obama administration, my advocacy abilities which are very important in this role, and my understanding of issues that are fundamental to the relationship with Canada—trade, energy, environment, intellectual property, and others,” he says. “And I did work in the White House until one week ago.” Former ambassador to Canada Gordon Giffin, who was also a practising lawyer and worked on Bill Clinton’s campaign, then helped staff his White House before being tapped for the Ottawa posting in 1997, says Jacobson has the experience and high-level contacts to do well at the job. “I think he will be a catalyst for bringing about constructive solutions to some of the challenges we confront,” Giffin says.

The great-grandson of poor immigrants from what is now Ukraine, Jacobson was born in Chicago and spent his early years in an apartment building on the city’s North Side occupied by his grandparents, two of his grandfather’s sisters, and several aunts and uncles. As he begins to tell how his mother had to carry him and the groceries up to their third-floor apartment, his wife interrupts. “You’re missing the point!” Julie says. “The point is the young prince was born. There were all these old relatives and one little baby boy!” she laughs.

Jacobson grew up with two younger sisters, and is very proud of the fact that he was the first in his family to go to college. That’s not to say his is a rags-to-riches tale. His grandfather had worked as a janitor in a real estate firm until the top boss noticed his smarts, put him through law school, gave him a job and put him on the path to becoming one of Chicago’s leading real estate attorneys. His mother had been a homemaker, but with her sharp mind, organizational skills and scrupulously labelled shelves in the linen closets, Jacobson is convinced that, had she been born later, “she would have been chairman of the board of Exxon.” His father had served in the U.S. Navy during the Second World War, and later turned a garage-based medicine-cabinet-making business into a successful company. Jacobson spent most of his childhood in the well-heeled Chicago suburb of Highland Park. Both his parents were “very conservative Republicans,” he says. “Don’t ask me why.”

Jacobson set off to Johns Hopkins University in Baltimore to study political science and economics. “He didn’t realize until he got there that it was not co-ed,” interjects Julie, while the ambassador’s face turns red. As a student, Jacobson worked for the city of Baltimore, getting to know young local politicians who have since risen to powerful positions, such as the Democratic congressman Steny Hoyer, now the majority leader in the House of Representatives, and Ben Cardin, now a senator from Maryland. He earned a law degree from Georgetown University Law Center in Washington in 1976 and began practising corporate law in New York City, before his mother became ill with cancer and he moved back to Chicago. What was intended as a temporary move became a three-decade long career with Sonnenschein Nath & Rosenthal LLP. It was there that he met his wife, then a student at New York University’s law school, who had a summer job with the firm.

The young lawyer quickly earned a reputation as a technology fanatic, and in 1999 was organizing networks for Chicago’s Internet start-ups and nanotechnology companies. “I am a geek,” Jacobson happily admits. “When personal computers first came out, I used to stay up until three or four in the morning with the parts all over the floor, just because I wanted to understand it.” Jeff Lennard, a former law partner, remembers him trying to find ways to use the newest technology in the courtoom. “I remember him designing complex visual graphics to explain how traffic patterns moved in a major rail merger we were opposing. It was hard to visualize and he found ways to use computer graphics in the days before PowerPoint.”

This week, Jacobson and his wife are planning to kick off six weeks of travel across Canada. “I want to meet as many Canadians as I can and try to understand what they really think,” he says. The goal is to visit all 10 provinces by the end of November. They are starting with a trip around Quebec, then heading out to the Prairies for 10 days, followed by a visit to British Columbia before setting out to the Atlantic provinces. “I’m trying to do as much of it as I can on the ground—by car or by train,” he says, recalling a long-ago road trip from New York to Los Angeles during which he “learned more about the United States than in hundreds of times flying over it.” The North may be on the agenda for next summer.

Jacobson has heard Canadian complaints about border “thickening” and wants to see for himself. He notes that U.S. stimulus funding has allocated money for improvements to border infrastructure. “With regard to whether there are other things we can do, I want to reserve judgment,” he says. “ I want to see what it’s like for ordinary people—I’m not sure I will, honestly, because I am the U.S. ambassador—but I want to get as much information as I can. Our goal is not to annoy people, or increase costs, or destroy economies. Our goal is to protect our citizens. I’m going to pay very close attention to see if there are things we can do to improve security or improve convenience. We can probably do both.”

The Jacobsons have a daughter, Wynne, 21, at the University of Colorado, and a son, Jeremy, 20, who is a first-year student at McGill. Julie, who has worked on literacy projects and sat on library boards, is already working on creating a borrowed art collection for the official residence, making use of a U.S. State Department program that enables missions to borrow some of the finest American art from U.S. collections. She says she has fallen in love with Canadian art, and has obtained special permission to create a mixed collection, half-American, half-Canadian. “This is a whole new approach to art in embassies,” says Julie, who has been working with the National Gallery in Ottawa and Chicago’s Art Institute. She has her eye on works by the Group of Seven and Emily Carr, and on American landscape painters, including one particular Georgia O’Keefe painting of Canada. And she was thrilled at the art she saw at Rideau Hall: “Everything there is fantastic.” She envisions turning the residence, with its master chefs and sprawling grounds and majestic views of the Ottawa River, into something of a cultural hub. “There are a lot of Canadian authors I admire. There are a lot of Canadian musicians that I admire,” she says, adding, “One of my greatest goals is to get k.d. lang to our house.”

As for Jacobson’s priorities, he talks in broad terms about his marching orders from the White House. “Trade, energy, border, our respective roles in international affairs and the fact that we stand shoulder to shoulder and to continue that—those are the most important things I will have to address,” he says. “And I am quite confident that there will be things I’ll have to address in the meantime that I can’t fathom yet.”

In the meantime, he may also indulge in the occasional cigar. “I told him I was jealous since now he was moving to Canada he would have an endless supply of Cuban cigars,” says Duane Quaini, former chairman of Sonnenschein Nath & Rosenthal, who describes Jacobson as “the best multi-tasker I’ve ever known” and a “happy” person who litigated without resorting to meanness. Quaini is planning to visit the Jacobsons in Ottawa, and says the new ambassador “promised me he’d have Cuban cigars on my arrival.” Asked about this potential breach of the U.S. embargo against the Castro regime, Jacobson demonstrates he’s getting the hang of the ambassador thing. “No comment,” he says.

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