In Chicago, he worked at the Wood and Oakley law firm, which specialized in managing bonds.

[1] While working as a lawyer, Oakley continued to write about classical studies, Franciscan missionaries, and peaceful conflict resolution.

This position led to opportunities to serve in other areas, and he resigned the committee to join the American Red Cross Commission to Greece.

[1][2] Oakley died from heart disease on the ocean liner Conte Blancamano on December 15, 1929, while en route from New York City to Naples, Italy.

[1] He was cremated, and his ashes were buried at Forest Hill Cemetery in Madison, Wisconsin.