McCaleb was elected as a Republican to the Oklahoma House of Representatives in 1974. He remained in the House until 1983. In 1978, McCaleb's colleagues elected him House Minority Leader. He remained in that position until his retirement from the Legislature.
Following the end of Bellmon's term, McCaleb became the President of the Oklahoma Good Roads and Transportation Association, a lobbying group dedicated to advocating safe, efficient and affordable state streets, roads and highways. He served as President until 1995.
Keating Administration
In 1995, incumbent Governor of OklahomaDavid Walters choose not to seek re-election as Governor. Republican Frank Keating was elected to succeed him in that position. Keating appointed McCaleb to serve as his Secretary of Transportation. Additionally, Keating appointed McCaleb as the head of both the Oklahoma Department of Transportation and the Oklahoma Turnpike Authority. McCaleb remained in all three positions until July 2001 until he resigned to take a federal government job. Keating appointed Herschal Crow of Tulsa to succeed him as Secretary.
George W. Bush Administration
As a member of the Chickasaw Nation, McCaleb was appointed by Republican President George W. Bush in 2001 to be the Assistant Secretary of the Interior for Indian Affairs in the Department of the Interior, reporting directly to Secretary of the Interior Gale Norton. As the head of the Bureau of Indian Affairs, McCaleb was charged with the administration and management of of land held in trust by the United States government for Native Americans, Native American tribes, and Alaska Natives. McCaleb remained in that position until 2002, when he returned home to Oklahoma.
Chickasaw national service
After leaving federal government service, McCaleb began work as advisor to Bill Anoatubby, Governor of the Chickasaw Nation. McCaleb has been tasked by Governor Anoatubby with the development of long-term economic development plans and policy. Governor Anoatubby appointed McCaleb to the board of directors of Bank 2, a financial industry firm completely owned by the Chickasaw Nation. Governor Anoatubby also made McCaleb the Chairman of the Board for Chickasaw Nation Industries, a wholly owned subentity of the Nation responsible for promoting economic development for the tribe.
Personal life
McCaleb is married to his wife Georgann and together they have four children and twelve grandchildren.