[1] Daly was also a supporter of the single tax schemes advocated by followers of the popular political economist Henry George.
He opened his own business, the Portland Monotype Company, the same year, and soon saw his income nearly triple from his previous US$35 per week wages.
At first greeted on the council as a successful member of the business community, Daly soon found he had enemies among Portland's establishment, most notably his former employer, the Oregonian.
A characteristic battle between Daly and the paper involved the rising number of "jitney" operators running competition with the Portland Railway, Light and Power Company's monopoly on transportation within the city.
The Oregonian viewed the situation as a threat to an established business providing an essential community service by opportunistic upstarts engaging in unfair competition, while Daly defended the jitneys, whose owners had organized a union to defend their interests, as American individual ingenuity and collective organizing at its best.
In 1917, Daly became a Republican mayoral candidate against fellow councilman, George Luis Baker, a flamboyant character who had made his fortune as a theater operator, and was widely regarded as having more interest in shameless self-promotion than the people's business.
The election coming just a few months after the Bolshevik Revolution, the revelation and the Oregonian's characterization of it as evidence of Daly's unpatriotic and dangerous radicalism was enough to alarm a substantial number of the city's voters.