[4] Following his service he became a prominent attorney in Portland, Oregon, where he often defended labor unions and "radicals" including birth control activist Margaret Sanger.

[5] He began to write, became a frequent contributor to The Pacific Monthly magazine, and was a leader of Portland's literary community.

Like many Cleveland Democrats, including his long-time friend Mark Twain, Wood joined the American Anti-Imperialist League.

[6] In 1927, he wrote in Heavenly Discourse that the "city of George Washington is blossoming into quite a nice little seat of empire and centralized bureaucracy.

His love of painting generated numerous studies of landscapes and points of interest along the Oregon and California coastline.

He also memorialized some of his favorite places in watercolor including Keats' grave and vistas from his home in Los Gatos, California.

[11] The house was built in 1925 on a 34-acre property, with an entry way featuring a wrought iron gate flanked by two large white cat sculptures, named Leo and Leona.

[11] His friends included Ansel Adams, Albert M. Bender, Clarence Darrow, Eugene Debs,[12] Emma Goldman, Chief Joseph, Childe Hassam, Robinson Jeffers, Margaret Sanger, and John Steinbeck.