Gilcrease's early education was limited, and took place in one-room schools in Indian Territory. As a boy, he was often called "Indian Tom." Gilcrease attended Bacone College, where his most influential teacher was Alexander Posey, who taught his students the arts, sciences, writing, and about their American Indian heritage. The latter included learning of the Trail of Tears and important American Indian leaders, such as Sequoyah and Sitting Bull. Also, instruction on how to make bows and arrows and to hunt, and about the operations of the Creek National Council at Okmulgee. After Bacone College, Gilcrease enrolled in the Kansas State Teacher's College (renamed in 1974 to Emporia State University) at Emporia, Kansas.