Hales was elected to Portland City Council in 1992. He was sworn in as a City Commissioner in January 1993. During his tenure on the city council, Hales conceived of and won voter approval for the first parks bond measure in over 50 years, funding construction of two new community centers and over 100 park improvement projects across the city. Hales completed the first phase of the Portland Streetcar system, the first urban streetcar in the US in almost 50 years. He also completed the planning of the Pearl District and South Waterfront redevelopment areas, which were designed as dense, transit-oriented "new urban" neighborhoods. Hales' advocacy for transportation — summed up in his stated goal to make Portland "the best European city in America" for non-auto transportation — earned him the nickname, "Choo-Choo Charlie". One of Hales' more controversial initiatives as a city commissioner was diversifying Portland Fire Bureau workforce. He hired the first chief from outside the Bureau ranks, and created an apprenticeship program that added over 80 women and people of color to what had previously been a 99-percent white, male organization. He also became the only Portland politician to vote against Joint Terrorism Task Force involvement. Hales' attendance declined in 2001 during his campaign for the executive director position of the Port of Portland. At the end of May 2002, part way through his third term, Hales left to take a position with HDR, Inc., an engineering firm, where he managed planning and design of new streetcar lines in cities across the country. Following his departure from City Council, Hales told Willamette Week that he considered the 1994 parks bond measure and the streetcar to be his greatest achievements while in office.
Mayoral tenure
In 2011, Hales announced that he would be a candidate for mayor in 2012. On November 6, 2012, he defeated challenger Jefferson Smith, receiving 61% of the vote. He assumed office on January 1, 2013. During the first two years of his tenure as mayor, Hales confronted the city's largest-ever budget shortfall — $21 million — and emerged with a balanced budget, as well as conservative budgeting practices that allowed in enough revenue for supplemental budgets. Hales also reformed police practices, prioritizing community policing through walking beats and his choice in police chief, the community-minded Larry O'Dea. Along with Commissioner Steve Novick, Hales in 2014 proposed $46 million in new fees to pay for street maintenance and safety improvements, such as filling pot holes and building sidewalks. On March 6, 2015 Hales announced he would seek reelection for the 2016 mayoral election. In September, State Treasurer and former county commissionerTed Wheeler announced his intention to run a well-funded campaign against Hales. A month later Hales abandoned his reelection bid, stating, "So when confronted with a choice between giving my full effort to the job of being mayor and spending that energy on a long and consuming re-election campaign, it's an easy choice. Therefore, I have decided not to file for re-election." Wheeler won election in May 2016 with token opposition. On November 3, 2015, Hales and the city government passed a resolution opposing the local expansion of fossil fuel infrastructure. Hales faced controversy over his decisions regarding Portland's homeless issue. Hales initially declared a housing emergency in 2015 before experimenting with a "Safe Sleep Policy" which promoted non-enforcement of anti-camping laws on sidewalks and rights of way, which was promptly met with lawsuits from local businesses and neighborhood groups. He was protested by residents adjacent to the Springwater Corridor Trail,
Criticism
Hales was criticized as failing in oversight of the Portland Police and effort to gain accountability. In an editorial summarizing his single term, The Oregonian called Hales "imperious and clueless" and wrote Hales squandered opportunities to support public oversight, picked an unwinnable fight with a Federal judge, failed to streamline the city's "byzantine" police-accountability system, and failed to discipline police chief Larry O'Dea, who while drinking and playing with a gun shot an acquaintance. Hales received public criticism during his 2012 campaign for voting eight times in Oregon while a Washington resident. From 2004 to 2009, he claimed tax residency at his wife's Stevenson, Washington home. Oregon taxes income in Hales' bracket at 10.8 percent, while Washington has no income tax.
Personal life
Hales married his second wife Nancy in 2004. An avid backpacker and sailor, he spent a month sailing around the San Juan Islands after his term as a city commissioner, and then went to work for HDR, Inc. After his mayoral term, he spent 18 months sailing and then returned to HDR.
