“Right now, my fear is there are a lot of people with my kind of politics who are very excited about the results of the last election,” he said, “and they think all things are possible.”
Looper’s client, Gov. Kate Brown, wants $2 billion in new taxes for education, another $700 million for health care, a bill capping carbon emissions — and more.
Looper calls himself an “unabashed economic liberal” and says he hopes the governor and Democrats can find a way to meet their goals. But he worries that they could overreach and fulfill the worst characterizations of Democrats as “coming at you for a record amount of taxes, and they haven’t managed the state any better.”
The 49-year-old consultant, a bearish, quick-witted man with a yen for poker, could wind up playing a big role in helping shape that ambitious legislative agenda.
After Looper helped guide Brown to victory last year, she asked him to keep watch on the issues that could wind up being referred to voters after legislators act. It could be a long list, ranging from campaign finance reform to a major tax package for schools.
Looper played a similar role when Democrats last won voter support for a tax package – consisting of a big increase in the corporate minimum tax and higher rates for more affluent individuals — to fund schools and other government services. That was in 2009 when lawmakers were hunting for more money in the depths of the Great Recession.
Then-House Speaker Dave Hunt said Looper was brought in early to help shape the tax package, which Democrats correctly assumed would be referred to the ballot.
“He wasn’t dictating what was in the package, but he was showing us very clearly and reminding us where Oregon voters were,” Hunt said. “One of the beauties of Kevin Looper is he will just be a constant reminder of what can be passed by voters, what is within the art of the possible.”
Back then, moderates and business leaders were urging Democrats to make most of the taxes temporary — just long enough to get Oregon past the recession. But Looper’s central insight – based on polling and focus groups – was that the package was actually more compelling to voters if the taxes were permanent.
Voters, Looper said, were more interested in tax fairness than in filling a budget shortfall.
“If we tell them we’re only going to do it temporarily,” he said, “then they think those rich people and corporations are once again going to get off the hook.”
In the end, legislators made most of the taxes permanent. Looper then managed the campaign for what became known as Measure 66 and 67, which voters passed in early 2010.
Republican consultant Dan Lavey of Portland worked with Looper on two projects, an unsuccessful 2012 initiative to allow a private casino in east Multnomah County and a study of the tax system financed by business and labor. They dug into polls, focus groups and other data.
“There’s also the artistic side, the storytelling, and he’s very good at that,” said Lavey. “He understands both the art and science of politics.”
Looper often seems to be in the room when big decisions are made. He was, for example, part of the brain trust in 2014 when Gov. John Kitzhaber gathered his political and policy advisors to figure out how to deal with the failure of Oregon’s health insurance exchange website.
He also helped advise Kitzhaber about how to contain the scandal surrounding his fiancée, Cylvia Hayes, and her consulting business.
Critics of Looper – and in the gossipy little world of the Oregon campaign business, there are more than a few – say his ruthless side emerged during the last days of Kitzhaber’s governorship.
One oft-told charge is that Looper abandoned Kitzhaber to boost another client, then-Secretary of State Kate Brown, second-in-line to the governorship.
The story goes that Looper helped Brown draft a press release recounting what she described as a “strange” and “bizarre” meeting with Kitzhaber about whether he was going to resign or not. The release attracted big headlines that contributed to the pressure on him to leave office, which he soon did.
Looper said he only advised Brown to tell the truth.
“What I hate,” he said, “is people looking through the rear-view mirror saying, ‘Look at that, Kevin Looper orchestrated John Kitzhaber’s demise in order to get Kate Brown, his previous client, into the governorship.’
“Are you kidding me? You think I could predict all that crazy stuff we went through?”
This year, Looper could find himself at odds with some key Democratic players. Melissa Unger, executive director of the state’s largest union, Local 503 of Service Employees International, says she thinks the fears of the Democrats overreaching are overblown.
“I feel like we need to continue to do the things Oregonians want us to do,” Unger said, “and not be scared that a couple people could refer something to the ballot.”
Ever the strategist, Looper also said in a follow-up interview that he didn’t want to be portrayed as someone pulling strings in the backroom.
“On my own, I wouldn’t have gotten squat done,” he said.
In all of his campaigns, he added, “I could name like a dozen people that played critical roles. And my job was mostly to get out of the way, give them the opportunity, and I try to be the traffic cop that had the plan in mind while we were all talking together.”
A working-class kid from Omaha, Looper was a good student who managed to get into Yale University. He worked on two presidential campaigns in 1992, but he said his personal life fell apart after a later divorce. He moved to Portland in 2000 and “let myself get immersed in self-pity” as he lived off his credit cards, failed to pay his taxes and went heavily into debt.
Looper said his resurrection came when he climbed back into the campaign ring in 2004. He was asked to lead the Oregon operation for a national get-out-the-vote group financed in part by billionaire George Soros.
“He was not someone who was looking for a strict roadmap,” said Cecile Richards, who ran the overall organization, America Votes, and later became known as the head of Planned Parenthood. “He was someone who could go take a problem and solve it.”
Following that campaign, Looper became the first executive director of Our Oregon. That labor-backed political organization has played a key role in knitting together the state’s major progressive groups and cementing the power of the state’s Democratic machine.
Looper married again, to Jillian Schoene, who heads a group that trains Democratic women on how to run for office. They had a son and he established his consulting business. But in 2015, his health failed because of a genetic liver disease.
Looper’s prognosis was bleak. “It’s incredibly sad and frustrating,” said Schoene. “There are not enough livers.”
And then last year, Portlander Beth Bernard came forward to donate part of her liver. She’s another political consultant who is now executive director of the Oregon Trial Lawyers Association.
“I did what I could to help a close friend out, Period!” Bernard said in an email after declining an interview, saying she hadn’t liked the attention she received for her donation. The story of their simultaneous operations, at the University of California, San Francisco, was chronicled last year by Willamette Week.
“The second they hooked that thing up in the ICU and he woke up, he was like a new man and on the phone two days later working because he felt good for the first time in years,” Schoene said.
Looper said his harrowing experience has made him think about how he wants to focus his energy: “You don’t want to be the one that dies, and on the headstone it says, ‘He had so much potential.’”