Born on October 28, 1868, in
Gordonville,
Alabama, Caffey received an
Artium Magister degree in 1887 from Howard College (now
Samford University), an
Artium Baccalaureus degree in 1891 from
Harvard University, an Artium Magister degree in 1892 from the same institution and attended
Harvard Law School. He was a
Lieutenant Colonel in the Third Alabama Volunteer Infantry during the
Spanish–American War. He entered private practice in
Montgomery, Alabama from 1894 to 1902. He was Judge Advocate General for the office of the
Governor of Alabama from 1900 to 1902. He returned to private practice in
New York City,
New York from 1902 to 1912. He was a solicitor for the
United States Department of Agriculture from 1913 to 1917. He was the
United States Attorney for the Southern District of New York from 1917 to 1921. He returned to private practice in New York City from 1921 to 1929.
Allegations of political advocacy as United States Attorney Caffey briefly gained notoriety when his name was associated with possible political advocacy on the part of the Department of Justice. Just two weeks before the 1920 election,
John R. Rathom, publisher of the
Providence Journal, charged that the Democratic candidate for Vice President,
Franklin D. Roosevelt, had acted improperly while Assistant Secretary of the Navy in releasing sailors convicted on morals charges from
Portsmouth Naval Prison. Caffey, once the Attorney General had telegraphed his authorization, released a lengthy document from Justice Department files that discredited Rathom. A report in
the New York Times suggested that he may have acted with undue enthusiasm: "Some surprise was shown at the [D]epartment [of Justice]...that District Attorney Caffey had given the entire Rathom letter to the newspapers. He had been authorized, it was said, to make public 'excerpts'". ==Federal judicial service==