Gailor was enrolled in the preparatory department of, then graduated Bachelor of Arts from, Racine College in Wisconsin.

Bishop Charles Todd Quintard of Tennessee was an ardent supporter of Racine and its brilliant Rector, the Reverend James DeKoven (1831-1879).

St. James's and Racine were inspired by the scholarly philosophy and practice of William Augustus Muhlenberg (1796-1877), founder of two model schools on Long Island in 1828 and 1836.

He served in this position until 1925, when the Episcopal Church's first elected presiding bishop began his six-year term.

On June 25, 1924, he offered the invocation at the opening of the second day of the 1924 Democratic National Convention.