He hired the first chief from outside the Bureau ranks,[11] 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.

[13] At the end of May 2002,[10] 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.

[5] 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.

[24][25] 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.

[27][28] In September, State Treasurer and former county commissioner Ted Wheeler announced his intention to run a well-funded campaign against Hales.

Hales initially declared a housing emergency in 2015[35] 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.

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.

[2] 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.[5][39]