State Rep. Jefferson Smith’s campaign for mayor isn’t off to an awe-inspiring start. “It’s going terrible,” Smith, an East Portland Democrat, told WW last week. “I’m about to run into a wall.”

Literally. Smith woke up on his announcement day with an excruciating “corneal abrasion”—his eyeball had been scraped by a contact lens. He spent last week wearing a patch on his left eye.

Smith has since admitted to an “atrocious” driving record, as he described it to WW, including a 2004 conviction for driving while suspended. “Luckily,” Smith says, “the mayor has a driver.” Then The Oregonian reported that Smith, 38, hadn’t voted regularly until 2002 when he started the Bus Project, a nonprofit devoted to getting young people to vote. 

His opponents, former City Commissioner Charlie Hales and businesswoman Eileen Brady, spent the summer raising money—$154,000 for Hales; $189,000 for Brady. A poll, Smith says, would reveal “most people wouldn’t know who I am.”

He’s also untested in a big race. He’s famously scattered and frenetic, and some supporters say Smith’s two House terms haven’t prepared him for running City Hall.

Yet Smith’s entry into the mayor’s race has already changed the election in a big way. 

Hales and Brady got into the race to offer alternatives to Mayor Sam Adams. But with Adams out, Hales and Brady have lost their foil. Hales presents himself as the safe and responsible choice—old-school, bricks-and-rail tracks. Brady’s narrative: An eco-conscious working-mom success story. Neither has generated much enthusiasm.

Smith fills a void. He’s the “Keep Portland Weird” candidate unafraid to swear in public or indulge in self-deprecating humor. And he’s a hungry underdog.

After graduating from Harvard Law, Smith put in short stints at powerful firms in New York and Portland before founding the Bus Project in 2001. Four years ago, he bought a house in outer Southeast Portland when the district’s state rep, Jeff Merkley, was launching a successful campaign for U.S. Senate. Smith took Merkley’s seat unopposed.

At 38, Smith is the youngest candidate—Hales is 55 and Brady is 50—a difference he hopes to leverage by rallying the young-and-plugged-in demographic targeted by the Bus Project. His campaign already has 1,504 Facebook followers—more than Brady and Hales combined.

“A lot of people in my generation have taken for granted that this city is great and will always be great,” Smith says. “If it’s great for another 30 years, it’ll be because our generation, and the younger generation, makes it so.”

He also gives hesitant labor unions someplace to send their money. Hales had a testy relationship with the firefighters’ union while in office. Brady has played up her co-founder’s ties to New Seasons Market, a non-union store.

Smith has had labor backing before. One of his closest political friends is Joe Baessler, a Bus Project board member who’s now the political director of Oregon AFSCME, representing 1,000 city workers. Baessler didn’t return WW’s calls but has shown his devotion to Smith before.

“Screw off,” Baessler wrote in 2005 to a Bus Project critic on BlueOregon. “[Y]ou should be on your knees thanking god that Jefferson quit his six figure job in New York to come back here and help start [the Bus Project].”

No union has endorsed a candidate yet, but their leaders took notice of Smith’s entry. “No one was running before Smith stepped in that had any kind of real relationship with labor,” says Richard “Buz” Beetle, business manager of Laborers Local 483, which represents 850 city working, including Portland Parks Bureau employees. [Hales] has a lot of integrity. But he has no real understanding of labor unions. The same with the other candidate.”

He also has a stronger grasp of new media. Search for an entry on Hales or Brady on Wikipedia and you won’t find one. Instead you’ll get a flattering entry for “Jefferson Smith (Oregon politician).”

Smith, who was about $3,000 in the hole before his announcement, has already raised $31,000, according to this campaign. And he says criticisms of his lack of managerial experience are “bullshit.”

“I’ve directly managed smaller budgets, and bigger budgets,” Smith says. “I placed talent directly for 10 years. I managed the formation of a half-dozen organizations. I pick good people. I would put my leadership capability up against, how shall we say, other options.”

We’ll have more than a year to find out. His presence likely means one candidate won’t win a majority in the May 2012 primary, forcing a runoff the following November. Given his start, Smith has little room to go anywhere but up.

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FACT: Smith’s father, R.P. (Joe) Smith, is a former state legislator and Umatilla County district attorney. His stepmother, Meredith Wood Smith, chairs the Democratic Party of Oregon.