His career as a religious leader in his own right commenced in the early twentieth century, when he began claiming to have been set apart to keep plural marriage alive by church president John Taylor in connection with the 1886 Revelation.

[5][6] Woolley's distinctive teachings on authority, morality, and doctrine are thought to provide the theological foundation for nearly ninety percent of Mormon fundamentalist groups.

[14] In 1922, Woolley related a spiritual experience that had allegedly taken place during his first mission, wherein he fell deathly ill and only recovered after the resurrected Jesus Christ, Joseph Smith, Brigham Young, and John Taylor intervened on his behalf.

[15][16] Between October 1886 and February 1887, Woolley served as a mail carrier for LDS Church leaders hiding from state authorities during the crackdown on Mormon polygamy.

The version which has assumed canonical status among Mormon fundamentalists was compiled by Joseph W. Musser in 1929, and includes the claim that Smith's appearance was followed by an "eight hour meeting" on September 27, 1886, at which President Taylor put five men (Woolley and his father, George Q. Cannon, Samuel Bateman, and Charles Henry Wilcken) under covenant to ensure that "no year passed by without children being born in the principle of plural marriage.

[24] Most Mormon fundamentalists believe that, upon his father's death in December 1928, Woolley succeeded him as senior member of the Council of Friends, and thus "President of the Priesthood" or prophet.

[28] Historians Marianne T. Watson and Craig L. Foster suggest Woolley may have married Edith Gamble, a Salt Lake City widow, as a plural wife around September 1923.

[29] According to Hales, Woolley made numerous extraordinary claims about himself throughout his later life, such as alleging that he had once been employed by the United States Secret Service to spy on LDS Church leaders.

Woolley made similar claims about Presidents William Howard Taft, Woodrow Wilson and Herbert Hoover, but said they "have broken their covenants".