McNary first held public office in 1892 when he became Marion County's deputy recorder, remaining in the position until 1896. In 1904 he managed his brother John's successful campaign to be district attorney for the third judicial district of Oregon. John then appointed his younger brother as his deputy, and Charles served as deputy until 1911.
Steve Neal, McNary's biographer, describes McNary as a progressive who stuck with the Republican Party in 1910 even when many progressives left the party in favor of West, a Democrat. McNary backed the Progressive Era reforms—the initiative, recall, referendum, primary elections, and the direct election of U.S. senators— of Oregonian William S. U'Ren, and he was an early supporter of public rather than private power companies. After West won the election, he chose McNary to be special legal counsel to Oregon's railroad commission; the appointee used the position to urge lower passenger and freight rates. Meanwhile, McNary maintained friendly relations with both progressive and conservative factions of the Oregon Republicans as well as with West.
In 1913 West appointed McNary to the Oregon Supreme Court to fill a new position created by the legislature's expansion of the court from five justices to seven. The youngest of the justices at age 38, McNary left the law school and private practice behind. He quickly "established himself as a judicial activist and strong advocate of progressive reform". A supporter of organized labor, McNary "consistently defended the rights of injured workers and was not hesitant about using the bench as an instrument for social change" such as an eight-hour work day for public employees. Trade unions supported McNary throughout his political career.
Several criminal convictions resulted from a "vice scandal" that sparked in Portland in November 1912 surrounding the city's gay male subculture; by the time McNary was seated, some convictions had been appealed to the court. He wrote the dissenting opinion in the reversal of the conviction of prominent Portland attorney Edward McAllister. The dissent was emotionally charged and "revealed a deeply seated personal discomfort with same-sex eroticism."
In 1914, the court moved into the new Oregon Supreme Court Building and McNary filed to run for a full-six year term on the bench. At that time the office was partisan, and McNary lost the Republican primary by a single vote to Henry L. Benson after several recounts and the discovery of uncounted ballots. After his defeat, he served the remainder of his partial term and left the court in 1915. On July 8, 1916, after a close multi-ballot contest among several contenders, the Republican State Committee members elected McNary to be their chairperson. He was seen as someone who could unify the progressive and conservative wings of the party in Oregon.
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