MAYOR CHARLIE HALES might have timed things a little bit better, given what's become of John Kitzhaber, the state’s former governor, who was toppled after a corruption scandal involving his fiancée.

Just weeks before a Portland City Council vote on redrawing the city's urban renewal districts, a landowner who stands to gain from the changes was conspicuously first in line when it came time to revive Hales' campaign account ahead of a likely re-election bid.

As the Mercury was first to note, Hales on January 13 accepted $5,000 from John Bollier, president of ubiquitous transportation contractor Stacy and Witbeck. It was the first major check, by several days, in what eventually became a gusher of campaign money from developers and others—some $21,000 altogether, as of press time.

Meanwhile, city sources say, Hales has spent months emphatically evangelizing for something that would make Bollier (who didn't return a call seeking comment) pretty happy.

A long-aired plan to stretch the city's Central Eastside Urban Renewal Area south around the so-called "Clinton Triangle"—ostensibly to goose development around TriMet's new MAX line to Milwaukie—would also snag some land owned by Stacy and Witbeck.

The boundary change would clear the way for millions in infrastructure fixes, like sidewalks and extended streets, paid through urban renewal funds. Notably, that city spending would save Stacy and Witbeck the trouble of opening its own wallet. It also would make the land easier to develop—and thus far more valuable.

Of course, it would be simple to overlook that perk if Hales' plan was universally beloved. But that's not the case. The League of Women Voters is vocally unconvinced the city needs to encourage development that seems to be arriving anyway. Urban renewal money, the League notes, comes at the expense of the city's general fund, as well as schools and Multnomah County.

"I share their concerns," says Commissioner Amanda Fritz, who's likely to vote no.

Neither Fritz nor the League of Women Voters would comment on Bollier's check.

"Somebody who held office before us decided not to do planning around station areas that were coming online," says Hales' spokesman, Dana Haynes. "We've been talking about it for nine months. We've been putting it in speeches. The timing [of the campaign check] is odd only if one chooses to take a snapshot."

Haynes' explanation is valiant. But at the same time, Hales and Bollier have shared some mutually beneficial history. Bollier, whose donations tend to line up with his business interests, gave Hales $7,600 during his last campaign. He also reportedly signed up to raise thousands more from other wealthy donors.

And the Oregonian has reported that Hales, not long after taking office in 2013, went out of his way to speed along land-use planning along the light rail line.

"The optics are not great," says Jim Moore, director of Pacific University's Tom McCall Center for Policy Innovation.

But it's also how things are done. Sadly. You tap your friends. And people with clout.

"Who has money?" Moore says. "Golly, it's the people who have business with the city. As long as Charlie's wife isn't involved, he'll be okay."