He entered politics as a member of the Portland City Council serving from 1877 to 1880. In 1880, he was elected to and served in the Oregon State Senate as a Republican. Simon represented Multnomah County in several districts during his tenure due to reapportionment, and served through the 1891 legislative session. During both the 1889 and 1891 sessions he served as the President of the Senate. Simon did not serve in the 1893 session, but returned to the state senate in 1895 and was again the President.