But for the dubious interference of the Oregonian, City Councilman Will Daly may have had the distinction of being Portland’s longest-serving mayor. Daly’s campaign to obtain leadership of the city was thwarted by the efforts of Oregonian editor Henry Pittock, who authorized staffers to burglarize Daly’s home. The result of the so-called investigation was a last-minute article that historians believe swayed just enough people to cast their votes for Daly's opponent, George Baker.

Although Daly died in relative obscurity, he still had a considerable impact on Portland city politics during the 1910s. He was a member of the Portland City Council in 1911-1913 and commissioner of public utilities in 1913-1917, the first years of the city’s new commission form of government. In both of those roles, Daly challenged commercial interests that he believed were bilking the public, positions that endeared him to the working class but infuriated business leaders.

Born to Patrick and Lucy Daly in Springfield, Missouri, in 1869, Will began work in the printing business when he was ten years old. For the next twenty years, he moved up the ranks in Springfield and became the foreman for the Springfield Leader-Democrat when he was thirty-one. After his mother died in 1901, Daly left Missouri with his wife Daisy, initially settling in Salem, Oregon. In 1907, they moved to Portland, where Will took a job at the Oregonian, a position he would hold until 1911.

A champion of labor and, according to historian Robert Johnston, a leader of the petit bourgeoisie, Daly rose to prominence as head of the Oregon State Federation of Labor. In 1909, he introduced labor leader Big Bill Haywood during a protest rally in Portland, cementing his reputation as a leading labor advocate among Portland’s working class. Daly drew his political strength from an agile coalition centered in East Portland that consisted of union members and small business owners. His appeal to both contingents was predicated on his background as a union Linotype operator for the Oregonian and as the owner of his own Monotype operation.

As city commissioner, Daly advocated for his blue-collar constituents, especially jitney drivers. The Portland Railway, Light & Power Company, a recently merged conglomerate of transportation and utility companiesthat owned Portland’s streetcar business, sought legislation and city ordinances to limit jitney operations in an attempt to sustain its monopoly on city transit. The debate dominated commission meetings in 1915-1917, and Daly’s vocal opposition led Mayor Russell Albee to take away his control of the city’s transportation portfolio.

Daly’s work as head of public utilities would also run him afoul of Portland’s upper class. He wanted to install water meters on every Portland property, a proposal that infuriated Oregonian publisher and editor Henry Pittock. Daly claimed, accurately, that Pittock schemed to provide water for his estate in the West Hills at substantial taxpayer expense. Daly’s positions would come back to haunt him, however, when he ran for mayor in 1917.

In one of the more sordid moments of Oregonian history, agents of the paper broke into Daly’s residence and stole his papers, among which was an unfinished application for membership in the Socialist Party. With United States entry into World War I, the anti-war Socialists were in poor repute across the nation. Even though Daly had not joined the party and had registered as a Republican in 1912, the Oregonian ran a story about his possible membership two days before the election. The newspaper’s campaign against Daly tipped the scales in favor of the Oregonian’s preferred candidate, Baker, who would win by only 1 percent of the popular vote.

After the election, Daly retired from political life and moved to the outskirts of southeast Portland, where he focused on his family printing business until his death in 1924.