Once he joined the Jolly Rogers, he was assigned to New Guinea as an Aircraft Commander and, with his crew and ship (which was dubbed Big Chief), Bearskin flew 46 combat missions. Some of the missions were incredibly dangerous. He later recalled that during one raid over Wewak, the flak was so thick that "it looked like you could walk on it."

After the war, Bearskin had a career as an Air Force officer, retiring in 1960 with the rank of Lieutenant Colonel. For the next 19 years he served in the civil service capacity before retiring in 1979 and moving back to his native Wyandotte, Oklahoma with his wife, Barbara Cannon Bearskin.

In September of 1983 Bearskin was elected Big Chief when the Wyandotte Tribe of Oklahoma elected him Chief of their tribe. Since then he has dedicated his efforts to the betterment of his people leading his tribe to become financially self-sufficient. He has also made considerable improvement in the tribe's health care, education, adult services, employment and emergency services.