Bus Boy

Jefferson Smith built a political machine. Now he's trying to drive it to City Hall.

Jefferson Smith

On a recent Saturday morning, a sleepy-eyed retired auto-parts worker named Gavin Griffin opened the door of his Sabin-neighborhood home to find a blond giant on his doorstep. 

The stranger—at 6 feet 4—first greeted the man's dog, Bella, a Belgian shepherd, before launching into his standard doorstep greeting: "I'm Jefferson Smith, and I'm running for mayor."

Griffin talked to Smith about crime: Thieves had broken into his pickup truck twice in the past three months. What was Smith going to do about that?

Smith showed sympathy by turning the conversation back to his own experience: Crime in his outer-eastside neighborhood is a big problem. "I got my car swiped," Smith said—and noted ruefully that police later found the vehicle, so he didn't get an insurance settlement.

Still, the two seemed to bond. But when Smith turned to go, he looked back at Griffin, who was wearing gym shorts and a T-shirt.

“Get some shoes on,” Smith said. 

Puzzled, Griffin agreed he probably should.

"I'm just glad you're wearing pants," Smith added.

Normally, candidates who knock on doors to ask for votes steer clear of cutting humor and sarcasm.


At another house, Smith talked education with a young father named Buddy Herrlinger for 10 minutes, then left the man gaping when he blurted as he stepped off the porch, "I'm opposed to public schools. I'm just against them.” 

Smith says his attempts at levity with voters make canvassing bearable. "I can only do this if it's fun," he says.

Mocking the very voters he's trying to woo captures the essential contradictions of Jefferson Smith.

He's a Harvard law graduate and two-term state legislator who founded a nonprofit that's grown into one of the highest-profile Oregon political movements in decades—and yet he often still acts like a college freshman.

"There are so many WTF moments with Jefferson," says Caitlin Baggott, who last year succeeded Smith as executive director of the Bus Project, the voter-engagement group Smith co-founded.

Baggott calls such moments "delightful." But for others, the cerebral man-child now running for mayor is a head-scratcher—the smartest kid in class who's too busy cracking jokes to bother buying textbooks. 

Smith joined the mayor's race late and has scrambled to catch up with the other two leading candidates—businesswoman Eileen Brady and former City Commissioner Charlie Hales.

Smith is a puzzling mix of brilliance, disorganization and earnestness at odds with his political wiles.

Over the past decade, Smith drove the Bus—as his organization is known—with hard work and the motivational skills of a revival preacher. He made it a magnet for young people who never knew they cared about political activism.

As the Bus grew, Smith's dominance of the organization sometimes lent the appearance of a cult of personality. 

That's transferred to this campaign, where Smith has presented ideas about making Portland a more equitable city but has mostly presented the idea of Jefferson Smith himself.

Smith says he's in politics to "do things, not be somebody." His allies point out—accurately—that he passed up earning millions as a lawyer for poverty-level wages. Smith leads the campaign in volunteers and Facebook friends, and earned two key labor endorsements—from the American Federation of State, County and Municipal Employees and the Portland Association of Teachers.

He campaigns like a July 4th sparkler: bright, firing off in many directions, and subject to abrupt flameouts.  

Smith's energy is legendary. He penned the Bus Project's best-known slogan—"VOTE, FUCKER"—at 3 am. He's loud, pumps out words faster than a laser printer and windmills his arms around so much some lobbyists call him "the crab." Salem insiders say Smith is, at 38, only now learning to listen more than talk.

He can be folksy one moment and impossibly dense the next, spewing out lists laden with jargon and punched up with words like "cognizable," "concomitant" and "technocracy." He even baffles friends with the term he uses for his job-creation strategy: "economic gardening."

"Jefferson doesn't talk to people the way they talk," says Joe Baessler, the Bus Project's first employee and now political director for AFSCME in Oregon. "He has a tendency to come up with his own phraseology.” 

Smith's ability to appear simultaneously brainy and incomprehensible isn't his only challenge.

There's also the matter of experience. He wants to run the City of Portland, which has nearly 7,000 employees and an all-funds budget of $3.5 billion. His proof he can do it: his experience in leading the Bus, which has 14 employees and a total budget of about $1.25 million.

Yet Smith is scattered and chronically late, and has shown an inability to handle basic administrative tasks. The Bus has routinely filed paperwork late or inaccurately. And there are serious questions about how transparent the Bus has been and whether its claims of nonpartisanship are a ruse as it plays favorites with Democratic candidates.

"Being mayor is not a job where you get to pontificate on the issues of the day," says Liz Kaufman, a veteran Democratic political organizer who has worked with Bus volunteers. "It's a serious job where you have to manage a big operation every day.” 

Kaufman says her dealings with the Bus convinced her not to support Smith, and she is leaning toward Hales.

Smith says he's worked hard to address his shortcomings, and takes pride in surrounding himself with the best and the brightest.

"I move fast and I talk fast," he says, "but I have the ability to zoom back and forth between the big picture and granular details."

Unbridled ambition and chaotic energy define Smith. But there is no greater influence on his political career than the unfulfilled ambition of his father.

R.P. "Joe" Smith traces his family tree back to Joseph Smith, who in 1830 founded the Church of Jesus Christ of Latter-day Saints (the founder was his great-great-great uncle). His great-grandfather became president of the Mormon Church.

Although Joe Smith, 76, is estranged from the church, he treasures his Mormon upbringing in a small Utah town.

“I grew up with a great sense of the gifts that I have enjoyed from my heritage,” he says. 

Joe Smith had lofty political goals. The legendary U.S. Sen. Wayne Morse was a close family friend. 

"When I was 16 years old, I knew I wanted to grow up and become a U.S. senator," he says.

But Joe Smith spent his career on the fringes of power. After winning election as Umatilla County district attorney, he lost bids for attorney general in 1972 and 1980. 

Still, he clung to a starry-eyed view of good government, which his son says he believes in above all else. 

"Dad's first governing value was making the world better," Jefferson Smith says, "which was different than taking care of your family."

Joe Smith, who is his son's unpaid legislative intern, says he's not living vicariously through Jefferson.

"But I feel a strong desire to leave things better than I found them," he says. "I feel Jefferson could be a great gift to those who come after me."

Jefferson Smith was born in 1973 and—he says—was probably conceived on the campaign trail. (His older brother, Lincoln, declined to be interviewed.)

His parents split, and from sixth grade on Smith grew up with his father in a historic Irvington duplex family and friends call the “Smith compound.” 

"It was the kind of place where you would find a copy of The Federalist Papers on the bookshelf," says John Wykoff, a boyhood friend of Smith's.

At Grant High School, Smith was student body president and was elected attorney general at Oregon Boys State. 

Smith was a high-energy prankster, better known for his quick thinking than for hitting the books. He says he was a comic-book nut and Blazermaniac, and aspired to be general manager of the Los Angeles Dodgers.

"He was a big, bouncy kid," recalls Grant High teacher Doug Winn, Smith's mock trial coach. "He knew how to boil things down to short phrases that condensed everything. His delivery was very measured but forceful."

Smith's mother died when he was a senior, and he ended up at the University of Oregon. He was, by his own estimation, a distracted and lousy student. After two aimless years, his father suggested he take a year off.

Smith worked with juvenile delinquents in Lane County and with underprivileged kids in Washington, D.C. 

That year, a friend suggested that Smith's erratic behavior was a sign of a bigger problem. Smith was examined and began taking medication for attention deficit hyperactivity disorder. 

"Medication helped," Smith says. "More importantly, I learned coping mechanisms."

Years of unambiguous success followed. Smith excelled during the rest of his time at UO. At Harvard Law School, he landed prestigious summer associate positions at three of the nation's leading law firms—Gibson, Dunn & Crutcher in Los Angeles; Covington & Burling in Washington, D.C.; and Wilson Sonsini Goodrich & Rosati in Silicon Valley—finished in the top 10 percent of his class, and won a coveted clerkship with Judge Alfred Goodwin of the U.S. 9th Circuit Court of Appeals.

Steve Calandrillo clerked with Smith and recalls his focus and extraordinary work ethic.


"He pulled several all-nighters," says Calandrillo, a professor at the University of Washington School of Law. "[He] put together really impressive memos for the judges.” 

One day in the basement of the federal courthouse in Pasadena, Calif., Smith and Calandrillo discovered a tiny elevator, its car about 3 feet tall. Smith folded his lanky frame and climbed in. 

Calandrillo hit the "door close" button and suddenly realized he had no idea where the elevator went or whether Smith could breathe. He ran upstairs and found the shaft led to the law library; the elevator was for hauling books. 

"He was fun-loving," Calandrillo says, "and he was taking this ride even though he never knew where it would come out."


Despite enormous promise, Smith's law career fizzled.

After his clerkship, he joined Wachtell, Lipton, Rosen & Katz, Manhattan's top-paying law firm, in 2000. 

He left a few months later, shortly after passing the New York state bar. Smith says he left because he did not want to represent tobacco companies. Smith says he failed to appreciate how big Wachtell's role was in defending big tobacco in national litigation.

"I should have come to grips earlier with how I felt about that," he says.

Smith returned to Portland and joined the city's largest law firm, Stoel Rives. Stoel lawyers declined to talk about Smith on the record, but his brief tenure there is legendary. 

Smith usually arrived late, slipping in the back door, and never checked his voice mail, which was usually full. Says one former colleague: "He was a very difficult guy to find."

Instead of tending Stoel assignments, Smith was working on what became the Bus Project.

The idea for the Bus percolated in 2001 among Smith and other friends interested in getting more young people active in politics. John Wykoff says they wanted to capture the spirit of Demo Forum, which operated in the 1970s, and XPAC, which operated in the 1990s.

Meanwhile, Stoel Rives wondered what it was paying Jefferson Smith for. As a law clerk, he had famously pulled all-nighters to write memos. But while at Stoel, he says, the only all-nighters he pulled were for the Bus.

As the Bus got rolling, Stoel Rives and Smith had what he calls a "mutual" parting. "If I begged to stay," Smith says, "I don't know that the answer would have been 'yes.'"

Smith threw his energy into building a organization that over the next decade would claim to register nearly 70,000 voters, hit 300,000 doors and graduate nearly 160 PolitiCorps fellows from a 10-week political boot camp.

The Bus has expanded to three other states, becoming a training ground for political staffers and at least three Democratic lawmakers, including Smith.

(Disclosure: WW co-sponsors with the Bus the election-year revue "Candidates Gone Wild.")

Smith served as director until 2011. For the first three years, he lived with his dad. He had a modest trust left by his mother and didn't take a salary until 2005, when he took $2,000. After that, his yearly salary never exceeded $40,000.

Joe Smith recalls sorting through a stack of Smith's unopened mail and finding an uncashed Stoel Rives paycheck for $4,000 that was two years old.

Smith was disorganized in other ways. He racked up at least seven traffic violations, and in 2004 got his license suspended for failing to appear in court. The Oregon State Bar suspended his law license three times for failing to pay dues. 

"I've got weaknesses like anybody else," Smith says. "If I'm attending to a particular objective and trying to accomplish it, I'll neglect details in my personal life."

But his disorganization spilled into work as well.


Of the three major mayoral candidates, only Smith has created something that is distinctly his. Hales ran city bureaus and worked in private business. Brady has management and marketing experience but has not run anything.

But the Bus is Smith's—in its ability to rally young voters, and in its sloppy record-keeping and lack of transparency.

The Oregon Secretary of State Corporation Division canceled the Bus' business registration three times—in 2002, 2004 and 2006—because it didn't file paperwork on time. 

Between 2005 and 2011, the Oregon Secretary of State Elections Division fined the Bus at least 10 times, for failing either to disclose its campaign finance activities on time or accurately. In May 2010, the Bus was penalized $632 for filing 107 transactions four to six months late.

The Bus Project calls itself a nonpartisan organization devoted to furthering democracy through engagement in the electoral process. 

In effect, though, the Bus is part of the Democratic Party machine. Documents show it sent volunteers to canvass neighborhoods almost always on behalf of Democratic candidates and causes. (Smith's stepmother, Meredith Wood Smith, is chair of the Democratic Party of Oregon, as Jefferson Smith's father once was.)

"I think it's a wholly owned subsidiary of the Democratic Party of Oregon," says Rob Kremer, treasurer of the Oregon Republican Party. 

Kremer's concerns about the Bus are similar to those expressed by U.S. Sen. Jeff Merkley (D-Ore.) in a March 12, 2012, letter to the Internal Revenue Service about Tea Party organizations.

Merkley and other Democratic senators want the IRS to crack down on "groups devoted chiefly to political election activities who operate behind a facade of charity work."

The Bus is actually three organizations under one umbrella: a charity, a nonprofit corporation and a political action committee. Money flows back and forth among the groups, prompting Kremer and other critics to question whether the charity—which allows donors to write off their gifts—is improperly operating an advocacy group for candidates and causes.

Smith and Baggott insist the Bus has an elaborate time-keeping system that tracks and allocates employee time among the three entities—that there is a strict separation between charitable and political activities and that everything is legal. The organizations have received a clean independent audit in each of the past two years. 

But the complex way the Bus operates means its work on behalf of political candidates isn't always transparent.

In 2010, WW questioned why the Bus' political action committee wasn't disclosing money it spent to send volunteers to help candidates. 

Only after that inquiry did the organization's PAC disclose it had spent $28,000 on 28 canvassing trips—25 for Democrats, three in a nonpartisan race and one for a Republican. 

In terms of Smith's mayoral hopes, a more pressing question for Portlanders may be whether the organization Smith built is effective.

"There were legitimate concerns about whether the Bus was just a place for the cool kids to have fun," says Josh Kardon, former chief of staff to U.S. Sen. Ron Wyden (D-Ore.) and an Eileen Brady supporter. "But Jefferson created something that works and has proved its value over time."

Other political pros say the Bus provides scant benefit.

"My experience was, the results weren't great," says Patton Price, who ran the campaign for Rep. Jean Cowan (D-Newport) in 2006. "I didn't get reliable information back from the volunteers…many of them didn't record the level of interest or didn’t do so reliably.” 

Political organizer Kaufman says the Bus may work in Portland, but its volunteers are a cultural mismatch in other areas. "Shoving Portlanders down the throats of rural Oregonians," she says, "is fundamentally naive, lazy and ineffective."

Smith says political pros have long unfairly dissed the bus. "We went to districts that wanted us," he says. "And I think the volunteers made a difference."

Smith used the Bus Project to launch his own political career, winning a seat in the Oregon House in 2008. 

After living most of his life in Irvington, Smith and his now-wife, Katy Lesowski, a Bus co-founder, moved into the East Portland legislative district then-House Speaker Jeff Merkley vacated. (Merkley that year defeated then-U.S. Sen. Gordon Smith.)

Smith's performance as a legislator has been uneven. 

WW’s 2009 legislative rating of Portland-area lawmakers scored Smith “bad.” 

"Truly scattered," one lobbyist told WW. "Much better campaigner than legislator," said another.

His legislative focus raised suspicions he was already angling for statewide office. (He's told friends he'd like to be governor someday, and twice during the campaign said “governor” when he meant “mayor.”) 

Despite sponsoring bills aimed at reducing crime on the MAX in East Portland, Smith voted with rural legislators to keep gun records secret and is the only Portland lawmaker supported by the Oregon Gun Owners PAC.

In what he refers to as his biggest legislative achievement, Smith teamed with Rep. Bob Jenson (R-Pendleton) to make more Columbia River water available for Eastern Oregon agriculture. 

Smith's rural focus amplified fears he was a carpetbagger.

"My concern," says Guy Crawford, an influential Smith constituent, "was that he was an opportunist and was taking advantage of a majority Democratic district as a steppingstone to higher office."

In his second term in the House, Smith improved. "I'd give myself an A-minus," he says.

Although classmates Rep. Jules Bailey (D-Portland) and Rep. Chris Garrett (D-Lake Oswego) got meatier committee assignments, Smith rated "good" in WW's 2011 survey. (He helped his marks by lobbying lobbyists.) Smith passed bills to improve voter access and do energy retrofits for schools. But he got more attention for his staunch opposition to the Columbia River Crossing Project.

Crawford and other constituents say Smith has become a strong voice for East Portland.

"He has been a really outspoken advocate for a community that doesn't really have a spokesman," Crawford says. "And he's everywhere."

But now, Smith is doing exactly what Crawford initially feared—using his district as a political steppingstone. 

Yet Crawford is knocking on doors for Smith. 

"He'll do a hell of a job and is not going to forget where he's from," Crawford says. "He's from here now."

Although Smith's late entry into the mayoral race surprised City Hall watchers, House Democrats weren't surprised to see him ditching the Legislature.

"He's shown an ability to dig in and find an issue and actually get a bill moved," one says. "I think he sees himself as being limited here. Not caucus leader or speaker, because he's a big personality and has a rep for talking too much and being on the edge of doing something a little weird."

Smith says his legislative constituents convinced him he can do more for East Portland from City Hall than from the Capitol.

“It was serving my district that focused me on city issues,” he says. 

Smith is undeterred by critics such as former Mayor Vera Katz, who says he's not ready to be mayor. He sees a generational issue.

"We're no younger than they were when they came into power," Smith says.

Now, he just has to convince voters, using his inimitable style.

At campaign fundraiser at Bossanova Ballroom in late January, he gave hundreds of supporters a taste of what he gives voters on their doorsteps. 

"I will make a prediction in this race," Smith said. "We will not raise the most money. So give nothing! Get the hell out of here!” 

WWeek 2015

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