Oakes led a nineteen-month occupation of Alcatraz Island with LaNada Means, approximately 50 California State University students, and 37 others.

[4] While working on the Claiborne Pell Newport Bridge, Oakes met and married an Italian/English woman from Bristol, Rhode Island.

While studying at SFSU, Oakes worked as a bartender in the Mission District of San Francisco, which brought him in contact with the local Native American communities.

[5][citation needed] Oakes was disappointed with the classes offered at San Francisco State and went on to work with an anthropology professor, Dr. Bea Medicine, to create one of the first Departments of American Indian Studies in the nation.

He developed the initial curriculum[5] and encouraged other American Indians to enroll at San Francisco State University.

[4] In 1969, Oakes led a group of students and urban Bay Area American Indians in an occupation of Alcatraz Island[9] that would last until 1971.

The historic occupation was made up initially of young indigenous college students from around San Francisco and UCLA.

He helped the Pit River Tribe in their attempts to regain nearly 3 million acres of land that had been seized by Pacific Gas & Electric.

[14] Soon after Alcatraz, Oakes was shot and killed near Annapolis, California, in rural Sonoma County by Michael Morgan, a YMCA camp manager.