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The History of Roslindale High School
by Patrick O'Connor
updated June 18, 2021


The building that was once Roslindale High School at 110 Poplar Street was built in two sections in 1924 and 1926. It was initially the Washington Irving Junior High School, and designed by noted architect Charles Howard Walker. In September 1936, a new junior high school (the Washington Irving) on Cummins Highway opened and the Poplar Street building became Roslindale High School.


Approximately 1200 students were enrolled on Thursday, September 10, 1936. The first headmaster, Ambrose B. Warren was appointed on April 27, 1936. His association with the Boston Public Schools began in 1908 when he joined the faculty of Mechanical Arts High School in the Back Bay. Previous to coming to Roslindale, he was head of the science department at Dorchester High School for boys.


During the World War II years, as many at 675 graduates of Roslindale High were in the various armed forces of the nation fighting in Europe. At the end of the school year in 1947, Mr. Warren announced his retirement.


Second headmaster was distinguished educator Gerald F. Coughlin. He joined the Boston Public Schools in September 1924, teaching and coaching football at Mechanic Arts High School. His time at Roslindale High was brief; beginning the new school year in September 1948 when he was appointed Assistant School Superintendent. A sudden illness led to his untimely death at the age of 46.


Thomas F. Gately became the third headmaster in September 1948. He began his career with the Boston Public Schools in 1924 at Jamaica Plain High School. In 1936, he joined the staff at Roslindale High School and was of great assistance to Mr. Warren in starting the school. He eventually was made head of the business department in September 1957.


His successor and fourth headmaster was Wilfred L. O'Leary, a Boston native and 1925 graduate of Boston Latin School. In 1942, he was called to military service and served four and a half years in the Army Air Force. He returned to teaching at Boston Latin School and in 1948. He passed away on July 12, 1995.


Fifth headmaster was William J. Cunningham. His career in the Boston Public Schools included teaching at Brighton High, Dorchester High, the High School Of Commerce and Charlestown High School. He retired in June 1971.


Sixth headmaster and first woman to lead the school was Helen M. Moran who arrived in September 1971. A Dorchester native, she studied at Simmons and Boston Teachers College. For three years she led the school. In August 1974 before the new school year, she was appointed assistant superintendent of schools for the Roslindale, West Roxbury and Jamaica Plain.


In the spring of 1974, US Federal Judge Arthur W. Garrity ordered a desegregation plan of the Boston Public schools with a goal of achieving racial balance throughout the system. In this plan, junior high schools became middle schools with grades 6-8 instead of 7-9 and district high schools added a ninth grade to become four year schools instead of three.


On September 12, 1974, Roslindale High School opened with a ninth grade class and a new headmaster, Donald G. Burgess. He earned degrees from Boston College and Boston State. He had previously taught at Boston Tech and English High School.


In 1973, the Mayor surprised the West Roxbury/Roslindale area with intentions to build a new high school in West Roxbury on a 14-acre site on the VFW Parkway. Original plans called for the school to be completed by September 1975 and to be a magnet school attracting students from all over the city.


In spring of 1976, US Federal Judge Arthur Garrity announced plans for the new school to replace Roslindale High School as a district high school. The last class to graduate from Roslindale High was the class of 1976. The new school opened on September 12, 1976. The Roslindale High School building remained abandoned and boarded up for ten years.


On Saturday, February 15, 1986, the boarded up building became elderly houseing and completed in May 1987. Today it’s known as Roslindale House at 120 Poplar Street.

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