In the fall of 1871 Miss Mary J. Patterson succeeded Miss Hutchins as principal of the high school, which was then located in the Stevens building on 21st Street during that year. Miss Patterson was graduated from Oberlin College with the degree of A.B. in 1862. So far as the records show, she has the distinction of being the first woman, of African blood, to receive a college education. When Miss Patterson attended Oberlin College, she took what was called the gentleman's course, which required a study of not only Latin and Greek, but the higher mathematics as well. It doubtless received the name gentleman's course, because at that time women did not as a rule pursue such studies. It is easy to imagine what an impetus and an inspiration such a woman would be at the head of a new school established for the youth of a race for which high standards and lofty ideals had to be set. She was a woman with a strong, forceful personality, and showed tremendous power for good in establishing high intellectual standards in the public schools. Thoroughness was one of Miss Patterson's most striking characteristics as a teacher. She was a quick, alert, vivacious and indefatigable worker. During Miss Patterson's administration, which lasted altogether twelve years, three important events occurred: the name "Preparatory High School" was dropped; in 1877, the first high school commencement was held; and the normal department was added with the principal of the high school as its head.

After Miss Patterson had served one year as principal, Mr. Richard T. Greener was appointed in 1872 to take her place. As Miss Patterson was the first woman of color to be graduated from Oberlin College, so Mr. Greener has the distinction of being the first man of African descent to be thus honored by Harvard College. He received his preparatory education in Boston, Oberlin and Cambridge, and was graduated from Harvard in 1870. A scholar and lawyer by profession, Mr. Greener has attracted attention by his essays and orations. He has held a number of important positions, having served as Professor in the University of South Carolina in the Reconstruction period, Dean of the Law School of Howard University, Chief Civil Service Examiner for New York City, and United States Consul at Vladivostock, Russia. After serving as principal of the high school nearly one year, Mr. Greener left it for fields of broader opportunity. Miss Patterson was then reappointed principal of the Preparatory High School and held the position till 1884, when Mr. F. L. Cadozo, Sr., succeeded her.

When Mr. F.L. Cardozo, Sr., was appointed to the principalship of the high school, the standard of scholarship required of the principals was certainly maintained. For he had the rare distinction of being educated at Glasgow University, Glasgow, Scotland. There he won two scholarships of $1,000 each in Greek and Latin. He also took a course in the London School of Theology, London, England, where he completed the three-year course in two years. He was once pastor of the Tremont Street Congregational Church, New Haven, Connecticut. Later he went to Charleston, South Carolina, where he engaged in missionary work in the employ of the American Board of Missions. Mr. Cardozo founded the Avery Institute in Charleston, and served as its principal until he became Treasurer of the State of South Carolina, in 1870. Under Governor Chamberlain he was Secretary of State for two terms.[353]

At that time there were 172 pupils in the school, but by 1886 the enrollment was 247, which was more than five times what it was when the school was established. In 1887-88, when the enrollment was 361, there were nine teachers, exclusive of the instructors in music and drawing. There was an increase of two teachers in 1888-89. From 1877 to 1894 the high school course consisted of three years' work. But in 1894 the course was enriched and enlarged by the addition of several electives and since then it has been lengthened to four years. The commercial department was established in 1884-85 and in 1887 a business course requiring two years of study was added. This with a technical course also requiring two years of study laid the foundation of the Armstrong Manual Training School. Girls were given an opportunity of taking up domestic science and boys military drill.[354] Referring to the school in 1889-90 Superintendent Cook said: "This school is growing, not only in number but in a condition to perform better and more useful work. In the practical importance of subjects taught and in their better and increasing provision for preparing pupils for business life there is recognition of the fact that practical usefulness is the great end of intellectual discipline."[355]

It was during Mr. Cardozo's administration that the high school was moved from the Miner building to a new structure in 1891. So far back as 1874 Mr. Cook urged the construction of a suitable building for the high school. But it was not until 1889-90 that an appropriation therefor was made.[356] This building, known as the M Street High School, was erected on M Street, near the intersection of New York and New Jersey Avenues, where the institution remained until it moved into the Dunbar.

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.

Mr. William Tecumseh Sherman Jackson succeeded Mrs. Cooper in 1906. He was educated at Amherst College which conferred upon him the degrees of A.B. in 1892 and A.M. in 1897. He thereafter pursued postgraduate studies at the Catholic University of America. Mr. Jackson's twenty-five years of service have all been in the high school. He was teacher of mathematics from 1892 to 1904, principal of M Street High School from 1906 to 1909 and has been head teacher in the Department of Business Practice from 1912 to the present time. In commenting upon Mr. Jackson's work, one of his superior officers declared that he "introduced the individual promotion system, stimulated interest in athletics and fostered the school spirit."

Mr. Edward Christopher Williams succeeded Mr. Jackson as principal of the M Street High School in 1909. He was graduated from the Central High School in Cleveland, Ohio, holds the degree of B.L. from the Western Reserve University, and an honor certificate from the New York State Library School. He was Librarian of the Western Reserve University from 1894 to 1909, and was instructor in bibliographical subjects in the Western Reserve University Library School from 1904 to 1909. After serving seven years as principal of the M Street High School, he resigned June, 1916, to accept a position in Howard University as Librarian and Director of the Library School. Mr. Williams achieved success as an administrative officer while principal of the M Street High School.