He moved in 1859 to St. Louis, Missouri to practice law for a year before he returned to Kentucky to enlist in the Confederate Army.

[8] In 1893, she was appointed to the Board of Lady Managers of the World's Columbian Exposition at Chicago[9] and supported the Kentucky Equal Rights Association lobbying efforts.

[3] While Cantrill was Lieutenant Governor, Jesse James robbed a stagecoach in Cave City, Kentucky, stealing a gold watch from Judge R.H. Roundtree, and a diamond ring from his daughter.

This reward was never collected for the proper criminal, as James was shot by a member of his own gang, but his guilt was shown by the possession of Judge Roundtree's gold watch.

During his second term as Circuit Judge, he became a national figure in the controversial proceedings against the assassins of Kentucky Governor William Goebel.

When Goebel died, Cantrill presided over the trials of the alleged assassins,[14] and backed the Democratic takeover of state government.