In 1888, McAndrew moved to Chicago and became one of the first five teachers at the new Hyde Park High School. He was promoted as the school's principal the following year.Tarvardian, p. 121Herrick, p. 143 McAndrew's tenure as principal would end in June 1891, when he was fired for insubordination. His firing was due to his refusing to certify a fraudulent diploma that falsely declared that a book publisher's son had successfully completed a course of study in botany that he had actually failed. Superintendent George Howland had ordered McAndrew to certify this diploma, arguing that the course was not a prerequisite for college. Thereafter, McAndrew momentarily left field of education and, in July 1891, became an advertising manager and district passenger agent in Saint Paul, Minnesota, for the Great Northern Railway.
