It was the first big battle of Jules Bailey's burgeoning political career, and the fresh-faced teenager thought he had it in the bag.
Classmates at Lincoln High School gathered to hear why Bailey - who ran unopposed for class treasurer as a freshman -- deserved the job again as a sophomore. His opponent wasn't even there.
"I was like, 'Pfff, well this is easy,'" recalled Bailey, now 36, trying to become Portland's second-youngest mayor in a century. "So I stood up, and I gave this very policy-oriented speech."
Then the auditorium doors swung open. In ran the challenger, dressed as Lincoln's cardinal mascot. He took the stage, literally throwing candy to voters.
Bailey lost in a landslide.
"I've been out, since then," Bailey said one recent afternoon, "to prove that good ideas can win."
In the years that followed, winning is all that Bailey has done.
Still the earnest policy geek, Bailey leveraged his Ivy League education and green-energy chops into a rising political career - serving three terms in the Oregon Legislature and two years on the Multnomah County Board of Commissioners.
But now, for the first time since high school, Bailey may find himself on the wrong side of a vote count, struggling once again to keep pace with a supremely self-assured rival, Oregon Treasurer Ted Wheeler. And it's not clear that Bailey's fully learned the lesson from his first and only political loss.
Interviews with more than 15 people who work and socialize with Bailey show a skilled and strategic politician who is still considered at his best when he's off stage. They say he's gifted at breaking down political complexities or brokering middle ground so opposing sides can share victory.
Yet instead of emerging as a hard-charging, firebrand lefty, Bailey has been unable to surface from Wheeler's shadow. One fan suggested that ideologically and politically, Bailey is a younger, less experienced version of Wheeler, perhaps with a higher upside.
Lacking major policy differences with Wheeler, Bailey hoped to contrast himself as a middle-class everyman more relatable than his millionaire opponent. He talked of being priced out of the rental market and the struggles of buying an affordable home, two compelling tales that, while true, reveal cracks under closer scrutiny. His strategy to limit campaign checks to $250 never packed the goodwill political payout he expected, either.
And instead of sprinkling candy-like candor into his policy rhetoric, Bailey acknowledges his debate performances sometimes feel too rehearsed. He's also struggled to speak clearly on the hot-button issue of whether cops should be immediately interviewed after using deadly force.
Now, heading into the May 17 election, Bailey finds himself a double-digit underdog. In limited public polling released last month, he tracked closer to the 13 other candidates in the mayoral race than to Wheeler.
Bailey said he knew this would be a hard campaign and believes he's gaining steam.
"I like being an underdog," said Bailey, who has support from teachers and police, among other influential groups. "I think there's some people who are going to be pretty surprised on Election Day."
Path to politics
Politics were present in Bailey's life essentially from the moment he was born.
There, at a Forest Grove hospital in November 1979, father Bob Bailey invited a friend for moral support: Bill Bradbury, Oregon's eventual secretary of state.
Although Bailey's parents divorced when he was young, he shuttled between their nearby homes just off Southeast Hawthorne Boulevard. Bailey's stepdad was friends with another politician, Multnomah County Chairwoman Beverly Stein, who would drop off Smithsonian Magazines for an adolescent Bailey. Bailey, in turn, was filmed for one of Stein's campaign ads.
"He actually had some pretty good exposure," the elder Bailey said. "And I have to say, that was a blessing."
Bailey took strong interest in the arts. He played violin and joined the Young Actors' Forum, where kids wrote plays. One of their later works, about diversity and prejudice, won a prestigious national education award.
For high school, Bailey crossed town to attend the renowned International Baccalaureate program at Lincoln. Then it was off to Lewis & Clark College, where he studied the environment and international affairs on a scholarship, working as a resident adviser to cover room and board.
After graduation in 2001, he taught English in Guilin, China, where he learned Mandarin. It was there that Bailey met his first wife, Amy Liqiong Wong. Bailey said she attended the university where he taught but wasn't one of his students. They were officially married in the United States in 2003, at 23, and filed for divorce at 30, citing irreconcilable differences.
Along the way Bailey earned two master's degrees from Princeton University. He also spent time working on three of Bradbury's political campaigns.
"I wasn't interested in just doing a favor for a friend. I was interested in having someone that competent working on the campaign," Bradbury said. "I knew he would be very, very, very good."
By 2007, Bailey landed an analyst gig for ECONorthwest and was the owner of a new home on a Southeast Portland cul-de-sac. When the House District 42 seat opened, Bailey thought about throwing in.
Over lunch one day, he and another young Democrat, Brent Barton from Clackamas County, made a pact. Each would run, and if only one proved successful, the winner would buy the loser a bottle of champagne.
No time for ideology
Bailey's path to victory included a key calculation: He would aggressively broaden his base, wooing unions, at the expense of an opponent who seemed far more likely to win their support.
Race for mayor
Name:
Jules Bailey
Age:
36
Family:
Wife, Jessica, a pediatrician; 7-month-old son, August
Education:
Bachelor's degree, Lewis & Clark College; master's degrees in public affairs and urban and regional planning, with concentration in economics and public policy, Princeton University
Work history:
Multnomah County commissioner, state representative, private consultant
Quote:
"I like being an underdog. I think there's some people who are going to be pretty surprised on Election Day."
It worked. Although Bailey didn't score every union endorsement, he got trades and Teamsters on board, besting the presumptive labor-friendly candidate in the May 2008 election.
"Don't concede anything to anybody," Bailey said, recalling his efforts to link a green platform with decent jobs. "I worked hard and got some good labor endorsements."
In the Legislature, Bailey was seen as a natural. He quickly ascended to House leadership, where he worked the Capitol to explain details and secure buy-in from fellow Democrats.
Bailey was pragmatic, too, knowing how far to push. In 2013, for instance, he carried a bill that drew fierce opposition from lobbyists but ultimately passed, creating new oversight of prescription-drug administrators.
"He's incredibly smart and intuitive and had a unique capability of being able to make a deal that got opposing sides together, going further than either side thought it could go," said former House Majority Leader Val Hoyle, who's now running for secretary of state and hasn't endorsed in the mayor's race.
Early on, Bailey labeled himself a "Dave Hunt Democrat" - after the former House speaker and majority leader, a moderate whom Bailey considered pragmatic and willing to work with all sides. It was a sometimes-uncomfortable fit, considering his ultra-liberal district.
Bailey was business-friendly, supporting several deals -- a 2009 stadium-financing deal, a 2011 tax-credit package package, Nike's 2012 tax deal -- opposed by legislators in neighboring districts. He also voted for the controversial Columbia River Crossing, surprising and enraging some environmentalists.
Conversely, he pushed for bike-lane and sidewalk funding, voted against a plan to curb pension payouts for government employees and sponsored a bill that paved the way for a state-run retirement plan for private workers - one of Wheeler's signature accomplishments.
"I don't have a lot of time for ideology," Bailey said.
Bailey's legacy is his green-energy legislation, saying he's motivated to combat climate change. He also worked as a private consultant on similar efforts, with those ties coming under scrutiny during this election cycle, especially because Bailey refuses to release a full list of clients.
One of Bailey's endeavors was with the Clean Economy Development Center. That nonprofit contracted with Cylvia Hayes, whose blurred role as consultant and first lady prompted Gov. John Kitzhaber to resign amid a criminal investigation in 2015. Records suggest the nonprofit hyped Bailey's skill and title as a lawmaker when seeking grant funding to pay for Bailey's work, something Bailey says he didn't know about and wouldn't have authorized.
In the Legislature, Bailey pushed through an energy-efficiency loan program, eliminated job-production requirements for renewal-energy projects in rural areas and established a loan program for retrofitting schools.
"For several years, Jules was incredibly influential and he was absolutely the most valuable champion for the environment that we had in the House," said Doug Moore, executive director of the Oregon League of Conservation Voters, which endorsed Bailey in the mayor's race.
In 2014, Bailey left the Capitol after winning election to the Multnomah County Board of Commissioners. There, Bailey focused on addressing homelessness, paying for a psychiatric emergency room and evaluating the strength of levees along the Columbia River.
"He gets the details but is also able to see the big picture," said County Chairwoman Deborah Kafoury, who endorsed Bailey. "You have to know how to work well with your colleagues. I see that really strongly with Jules."
Trying to be authentic
At campaign events, Bailey's voice often rises an octave above other candidates as he launches introductory remarks. His answers, compressed by the format of any given forum, can come across as canned.
"I just don't like trying to package what are complex issues into soundbites," said Bailey, who in 2014 played the role of Republican Rep. Dennis Richardson for Kitzhaber during debate rehearsal.
"I'm trying to be authentic," Bailey said.
At his tiny campaign office, above a liquor store inside a two-story strip mall on downtown's southern edge, Bailey seems at ease.
While answering an online forum one afternoon, he rattles off a list of beers with high bitterness. He recalls a Dave Chappelle skit about Prince, basketball and pancakes, thinking about dropping that reference into an answer.
"There's like three people who would get that," Bailey said.
Bailey, the father of a 7-month-old boy, soon retells a joke about the challenges of parenthood - specifically, the doubly challenging position of having twins - complete with some colorful language. Campaign aides burst into laughter.
On the stump, however, it's the same rehearsed stories. Over and over. Sometimes they grow in detail. And sometimes the facts don't fully add up.
At an arts event one afternoon, for instance, Bailey complained about being priced out of the Southeast Portland apartment he had moved to after his divorce. Other times, he recalls the burden of paying more than $2,000 a month for a 900-square-foot apartment.
What Bailey doesn't say: He lived in a sparkling new unit along Southeast Division Street, overlooking popular restaurants in a trendy commercial district.
Another time, at an event for the Native American Youth and Family Center, Bailey recounted the frustration he and his wife - Jessica, a pediatrician - found when trying to buy a home in 2015.
"We got outbid by all-cash offers, tens of thousands of dollars over asking," Bailey told the crowd. "We lost out 10 times in a row. And a lot of times, not just to human beings but to investment companies."
Bailey ended up buying a $379,900 house in "deep" Southwest Portland, one he could barely afford, he says in other settings.
But a review of real estate records shows Bailey put in offers for homes listed as high as $525,000. While nine of the homes did sell over list price, only two were all-cash offers. No home was purchased by a registered business.
Bailey stands by his account, saying he went off information he heard from his realtor.
Bailey said his overarching message remains the same: He couldn't afford a home in the neighborhood where he grew up.
"It was really hard," he said. "People want somebody who has seen that first hand."
Other parts of Bailey's personal life have also come under scrutiny, including his attendance at Imago Dei Community, a Christian church that considers both cohabitation before marriage and homosexuality a sin. Bailey said members include gay and lesbian couples and "young hipsters" who don't agree with the church's stance on those issues -- himself included.
"I don't just distance, I actively debate it within the church," Bailey said. "Institutions change slowly, and they don't change at all if people who disagree take their ball and go home."
Overtime, or game over?
If Bailey has a big a push coming, this would seemingly be the time.
But he backed out of a wacky campaign forum last week to attend the Portland Trail Blazers' series-clinching playoff win, leaving organizers to accuse him of "writing off" an event with Portland's young, progressive base. He defended the decision and posted game photos on his Twitter account.
Now, with less than two weeks remaining, the political question isn't whether Bailey can beat Wheeler in the primary. It's whether Bailey and the 13 other candidates can keep Wheeler below 50 percent of the vote, forcing a November runoff between the top two finishers.
"He legislated as a policy wonk, rather than a firebrand," said John Horvick, political director for polling firm DHM. "Because of that, it's been harder for him to draw a real contrast between himself and Ted Wheeler. They check a lot of the same boxes."
In other words, this race is anything but in the bag.
"Any day you live to fight another day," Bailey said, "is a good day."
-- Brad Schmidt
503-294-7628
@cityhallwatch