Pennoyer was a
Democrat most of his political career, but became a Populist in the early 1890s. In 1885 he ran for
mayor of Portland, but lost to
John Gates, partly due to his record of sympathy for the
Confederacy during the
American Civil War. He was re-elected in 1890 and served in the office until his second term ended on January 14, 1895. He refused to leave his office to meet Harrison at the state border. When Harrison came to Salem, Pennoyer kept him waiting in the train station (in the rain) and arrived 10 minutes late. That year the
Oregon Legislative Assembly created the
Oregon Attorney General office, and Pennoyer appointed
George Earle Chamberlain to that post. Pennoyer refused another request from Cleveland, who asked him to intervene when a group of unemployed workers, part of "
Coxey's Army", hijacked a train to travel east and join a mass march on
Washington, D.C. Pennoyer stated, "let Cleveland's' army take care of Coxey's army." His term as governor ended on January 14, 1895. Previously, while governor, he had opposed the
Bull Run Water Project, and at one point he vetoed a request for a $500,000 bond to finance its construction, claiming the water, because it originated in glaciers, would "cause goiter to the fair sex of Portland." The legislature came within one vote of overriding this veto, but it stood, and Judge Matthew Deady—who had drafted it—was so put out that he called the governor "Sylpester Annoyer." Ironically, during Pennoyer's term as mayor it fell to him to take the ceremonial first sip at the new water system's dedication ceremony. He took his drink of Bull Run water, set the goblet down and said, "No flavor. No body. Give me the old Willamette." He was the second mayor to sit in the new
City Hall that was completed in 1895. Pennoyer described the building as "expensive, unseemly and unhealthful." He served as mayor until June 1898 when his successor
W. S. Mason took office. ==Death and legacy==