Illustration by Ryan Alexander-Tanner

UNSURPRISINGLY, there's already an air of doom hanging over Commissioner Steve Novick and Mayor Charlie Hales' controversial push to raise millions in new revenue—via an income tax and business fee—for badly needed street paving and safety projects.

The day the plan came out, last Monday, November 10, the always-skeptical Portland Business Alliance (PBA) extended its middle finger—after spending months at the negotiating table, winning several concessions—and suddenly declared it couldn't support any plan with an income tax.

Around the same time, potent petroleum-industry lobbyist Paul Romain all but promised a ballot referral—only to be joined by the PBA, finally, on Friday, November 14.

(For what it's worth, transportation advocate Jonathan Ostar, director of OPAL Environmental Justice Oregon, has called the PBA's sudden opposition "a stab in the back"—noting the time the PBA spent successfully softening the income tax, taken as a signal it would hold its nose on whatever emerged.)

That opposition amounts to a massive headwind in the face of what's looking like a December 3 vote. And it's precisely the kind of deep-pocketed threat that killed city hall's last serious stab at raising transportation cash, back in 2008.

But it might be a blessing in disguise.

A ballot fight—if it's framed around rich Portlanders' distaste for an income tax that helps poor people—might actually turn out okay for Hales and Novick.

Unlike in 2008, Portland's not in a recession. We approved another local income tax, the $35 arts tax, in 2012. The city also went big for 2010's Measures 66 and 67, which raised income taxes statewide in defiance of the business community's sorrowful wails.

"City hall starts with an advantage," says Tim Hibbitts, a partner at respected local polling firm DHM Research—that is, assuming opponents don't successfully frame a campaign around waste and mismanagement instead.

"It's a liberal city," Hibbitts says. "It's not averse to taxes."

And Novick and Hales are still sitting on a nuclear option.

Back in July, after outcry killed Novick and Hales' first attempts at a flatter street fee, Novick paid DHM to examine whether some other revenue-raising options might prove slightly more palatable.

One of those options wasn't just palatable. It was popular. It was so popular it got the PBA and others back at the negotiating table.

A $55 million plan to aggressively tax Portlanders who earn $125,000 a year or more—and no one else—won support from a whopping 60 percent of respondents. For those who don't follow these things, that's the kind of starting line consultants dream about when putting measures on the ballot.

The flatter, more tepid tax Hales and Novick are pitching now—raising less while spreading the burden among the middle class—was meant as an olive branch for the PBA and others.

But if the PBA still isn't biting after wasting everyone's time, here's a question: Why bother? Why not revive the progressive tax the PBA hated but everyone else seemed to love?

"That's the challenge in front of them right now," Ostar says of Hales and Novick. "They've bent over backward as far as they can go."

And, yes... that means it's finally time for Hales and Novick to stand up. And stiffen up.