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Oregon became the 33rd state to join the Union on February 14, 1859. Oregon’s first two senators, Joseph Lane and Delazon Smith, took office on that day. Oregon’s longest-serving senators include Charles McNary (1917–1944) and Wayne Morse (1945–1969). Among those who rose to leadership positions is Charles McNary, who served as Republican whip and floor leader. In 1996 Ron Wyden won the first Senate election conducted by mail-in ballot.