He spent five years at Parsons before resigning to accept the presidency of Centre College, another private liberal arts school, in Danville, Kentucky.

[16] On July 7, 1922, Montgomery, while on vacation in Montana, submitted his resignation to the Parsons board of trustees by telegram[17] in order to accept the presidency of Centre College in Danville, Kentucky.

[21] During his term, he had plans to construct new fraternity houses to increase the number of students living on campus and secured 20% raises for faculty members.

Around the same time, the school was criticized by the Southern Association of Colleges for purportedly overpaying their head coach, Charley Moran,[25] and was accused of paying professionals to play in place of Centre students.

[27] Montgomery prevented the school from being dropped by the Association of Colleges and Secondary Schools of the Southern States, though the accusations were severe enough that Moran resigned the following year and star quarterback Bo McMillin, a popular choice to succeed Moran, declined for financial reasons.

[28] These events all culminated in a decision by Montgomery to begin de-emphasizing football in favor of Centre's academic standards.

[31] Tensions grew, in particular, between Montgomery and the student body, a large majority of which signed a petition to the board of trustees requesting his removal from office.

[37] Montgomery died on July 16, 1950—his eightieth birthday—at his home in Jonesville, Michigan,[38] and was buried in Cincinnati's Spring Grove Cemetery.