Cruikshank was born in Bradner, Ohio in 1902 to Jesse and Jessie (Wright) Cruikshank. His father was a grain dealer who modeled fair business practices and taught the young Cruikshank to respect the value of the labor of the farmers and workers with whom the family did business. The family eventually moved to Texas. Cruikshank worked as a deck hand on freighters on the Great Lakes and was a member of the Seafarers Union before attending Oberlin College. He transferred to Ohio Wesleyan University, where he graduated with a bachelor's degree in economics and theology.