In 1896 Dr. W. S. Montgomery was appointed principal of the M Street High School and held that position for three years. Dr. Montgomery was graduated at Dartmouth College, receiving the degree of A.B. in 1879 and the degree of A.M. in 1906. He completed the Howard University medical course in 1884. From the time Dr. Montgomery was appointed principal of the Hillsdale School in 1875 till the present, with the exception of two years spent in study at Dartmouth, he has served the public school system of the District of Columbia continuously.[357] In referring to his principalship of the M Street High School, one of his co-laborers states that it "was marked by a period of constructive work. He stood for high scholarship with a leaning toward the classical high school." Judge Robert H. Terrell succeeded Dr. Montgomery in 1899. He was the second principal of the high school to hold a degree from Harvard College. When a boy, he was a pupil in the public schools of the District of Columbia and was a member of one of the early classes in the old Preparatory High School. Mr. Terrell finished his preparation for college at Lawrence Academy, Groton, Massachusetts and was graduated from Harvard University in the class of 1884. In the fall of that year he was appointed a teacher in the high school and held that position for five years. In the fall of 1889 he was appointed chief of a division in the United States Treasury Department, where he served four years. In the meantime Mr. Terrell had studied law. He practiced that profession till 1889, when he was again appointed teacher in the high school. He was afterward promoted to the principalship. In 1902 President Roosevelt nominated him for a judgeship of one of the City Courts of Washington and Mr. Terrell resigned the principalship to accept this position. While serving as principal of the high school Mr. Terrell devoted much of his time out of school to preparing his boys for college. It is largely due to his influence that a goodly number of its graduates have completed their education at Harvard. Mrs. Anna J. Cooper was appointed Judge Terrell's successor and served from 1901 till 1906. Mrs. Cooper prepared for college at the St. Augustine Normal School. Like Miss Patterson, Mrs. Cooper was graduated at Oberlin College, receiving the degrees A.B. in 1884 and A.M. in 1888. With the exception of a few years Mrs. Cooper has taught in the public schools from 1887 to the present time. She is the author of "A Voice from the South," which received most complimentary notices in representative newspapers and magazines. During her administration in 1904 the course of study for the M Street High School like that of the other academic high schools was considerably changed and greatly enlarged.