Playing The Crazy Eights: Randy Leonard “wrote the book” on how to defuse opponents. IMAGE: ww photo illustration

Portland City Commissioner Randy Leonard so far has the kind of challengers whom incumbents running for re-election only dream of.

The first, Emily Ryan, is 23 years old, works two jobs and has no campaign staff. To qualify for public financing, she needs to collect $5 from 1,000 people by Jan. 31. As of Dec. 18, she had about 975 to go.

The second, Rev. Jerry Edward Kill, a 41-year-old painter, is refusing contributions because he’s not into “this whole competition thing.” Kill is not “running against” Leonard “but, rather, with him.”

How times change. In Leonard’s first re-election campaign, in 2004, he had to fend off an organized opposition of candidates drawn from neighborhood associations all over town. The “Crazy Eights,” as one former Leonard challenger described the pack, managed to whittle down his share of the primary vote to 53 percent, still enough to win without a November run-off.

This time, Leonard’s 2008 race is better described as a leisurely stroll followed by a long nap. By comparison, the other City Council contests are the Portland Marathon. The mayor’s race has attracted Commissioner Sam Adams, plus nine other candidates (soon to be 10, with the expected entry of well-known businessman Sho Dozono). And the council seat Adams is leaving has drawn six contenders, several of whom are actually campaigning.

“Remember that the filing deadline is in March,” Leonard says. “And also remember that I’m fully capable of making them mad enough to run against me.”

That’s unlikely. Neighborhood anger at Leonard has subsided, because, as Leonard and the Crazy Eights agree, the ’04 campaign taught their onetime bête noire how to listen.

The Crazy Eights’ main beef with Leonard was his disdain for process and consultation. Leonard ascribes his impatience to being a firefighter for a quarter-century. “When somebody says, ‘I’m trapped in a house,’ they don’t want me to do a work group,” he says.

Yet Leonard says he knew there was some truth to the charges against him. These days, Leonard says he tends to “listen with my ears and not my mouth.”

Several of Leonard’s 2004 opponents say his transformation is real.

“He really seemed to be very isolated and kind of proud of it. I don’t think that’s the case anymore,” says Bonny McKnight, an activist from the Russell neighborhood.

“His behavior has changed. That was what we were interested in modifying,” says Mark Lloyd Lakeman, cofounder of the nonprofit City Repair Project. “He’s more deferential. He’s still that shake-up-City Hall kind of guy, but he’s playing it smarter now. He’s not so much a bull in the china shop.”

Leonard has won points for improving customer service in the development services and water bureaus, and for championing the kind of livability issues that resonate with Portlanders, his ex-opponents say. His advocacy of biofuels and bicycles also played well.

If and when Leonard wins next year’s general election, he won’t have to run again until 2012. In the meantime, he is still being watched.

“When he gets a little out there, I remind him he won by one-half of 1 percent,” says Mary Ann Schwab, a Crazy Eights activist and retired public school secretary. Her math is a bit off, but the point is clear.

Aaron Hall, another ’04 Leonard opponent, hasn’t gained much love for the commissioner but says he’s too busy to challenge him again. So why won’t anybody else?

“Maybe he hasn’t messed up enough yet,” Hall says.

Leonard’s top five contributors (some donated through their companies):