WHERE THE SIDEWALK ENDS: Commissioner Randy Leonard says he’s heard enough complaints about aggressive solicitors that he wants to do something about it. IMAGE: Mike Perrault

In liberal Portland, guilt may cause even the hard-hearted among us to give dollar bills to panhandlers in the bus mall or stop to talk with earnest college students collecting money for Greenpeace.

But is liberal guilt any match for City Commissioner Randy Leonard?

Earlier this month, Leonard asked City Attorney Linda Meng to begin looking at how Portland could regulate the activities of people who aggressively solicit money on city sidewalks. That could include panhandlers who harass passersby and their clipboard-wielding, sidewalk-dwelling brethren—canvassers.

“It doesn’t matter to me if they’re selling magazines or trips to Hawaii or asking for cigarettes,” Leonard says. “I would never take an approach that targets one group of people.”

Leonard is no stranger to tackling urban hassles.

Two years ago, Leonard cracked down on taggers by crafting a new city ordinance that required Portland shoppers to show ID when buying spray paint. Stores, in turn, were asked to keep records of those purchases to help police officers track graffiti artists. In 2007 he also put a stop to the longstanding practice of reserving sidewalk space with duct tape to watch the Rose Parade each June.

The commissioner’s task ahead on panhandlers, canvassers and other forceful solicitors is considerably trickier. For one thing, Leonard does not want his possible ordinance to resemble Portland’s so-called “sit-lie” ordinance, which made it illegal to “obstruct” sidewalks downtown and in the Rose Quarter during busy hours.

In May, Leonard was the only city commissioner to vote against a proposal from Commissioners Nick Fish and Amanda Fritz to extend the sit-lie ordinance until this fall. Supporters of that extension wanted more time to evaluate the five-year-old ordinance and get public input on it.

Leonard said he was “appalled” by the measure, saying it targeted Portland’s homeless population, one of the city’s “most vulnerable” groups. In June, a Multnomah County Circuit Court judge ruled the ordinance unconstitutional. Then Portland police stopped enforcing it.

Leonard says he wants to avoid that kind of legal wrangling over panhandling by drafting a narrower ordinance that would be valid under the Oregon Constitution and that does not curb free speech.

Meng would not comment on what kinds of limits her office would advise.

“It’s not appropriate for me to discuss this,” Meng says. “[Commissioners] are allowed to ask questions that are protected by attorney-client privilege.”

David Fidanque, executive director of ACLU of Oregon, says there are two possible pitfalls for Leonard. He says a city can’t prohibit all soliciting because that would limit free expression. And a city can’t let, say, Girl Scouts aggressively sell cookies but prohibit Greenpeace from collecting money, because that’s considered content-based discrimination.

Last Saturday morning, as throngs crowded the South Park Blocks to attend Portland State University’s graduation ceremony or to shop at the Portland Farmers Market, the corner of Southwest Mill Street and 6th Avenue became a public exhibit of the complaints Leonard hears about canvassers.

There, across the street from a group of buskers playing bluegrass, was a man who identified himself only as Jason. A self-described out-of-work Californian who “came to Portland to find peace,” Jason greeted Portlanders with a wave or an outstretched hand.

“What’s your name?” he asked passersby who averted their eyes or, in some cases, stopped to talk.

An employee of an outfit called DialogueDirect out of New York, Jason was representing the Missouri-based charity Children International. Children International seeks sponsorships for poor children in impoverished countries. (It gives a flat fee to DialogueDirect for every sponsorship it brings in, but a spokeswoman for Children International would not say what that fee is, calling it “proprietary information.”)

Jason says he’s heard the complaints from Portlanders whom Leonard wants to protect. “You’re harassing us,’” people tell him.

But he dismisses the critics’ gripes about his work, which he says promotes goodwill and international understanding.

“People don’t think about children in dire poverty,” he says, simultaneously answering a reporter’s questions while making a pitch for Children International. (After speaking with WW, Jason said WW could use his comments only if this reporter sponsored a child. She didn’t.)

Jason was puzzled by the idea of the city regulating his interactions with people on city sidewalks.

“That’s like regulating humanity,” he says. “We need to empower humanity, and that’s what we’re here to do.”