The Glass family have the distinction of being the only known family to have four generations attend Sydney High School in its more than 140 year history. 

Sydney Benjamin (Ben) Glass grew up in Bulli, NSW. From Thirroul Public School he was awarded a scholarship to attend SHS at Mary Ann Street, Ultimo. It is presumed that he began at SHS in 1907, but this cannot be verified because the enrolment records of the school for that time have been lost. From the earliest editions of The Record, beginning in 1909, we know that Ben sat the Junior Public Examination in 1909 and the Senior Examination in 1910, matriculating with Honours in English. His poem “A Stockman’s Dream” was published in the first edition of The Record (December 1909). In 1910 Ben was a Sub-Editor of The Record and a member of the Library Committee, and he was appointed a prefect (1910 was the year in which the prefect system was introduced to SHS). Ben was a member of the Cadet Corps, attaining the rank of Lance-Sergeant. 

In The Record of June 1910 it is recorded that Ben had won the first prize of £10 in an essay competition open to all NSW Senior Cadets. The June 1911 edition reports that Ben had won the first prize of £40 in the Commonwealth wide competition. The winning essays of the Commonwealth and all State competitions were published in a book, “The Cadet and His Destiny” (1911). Of Ben’s contributions it is commented:

“As regards the Essays themselves the first, it must be admitted, bears clear impress of the faults and tautologies inseparable from schoolboy composition, but the most carping critic must allow that the more mature effort of Lance-Sergeant Glass is a  splendid achievement for a youth of seventeen.”

Ben served in the Army, within Australia, during World War 1. From about 1918 until his death in 1959, Ben practised as a solicitor in Sydney. He became a prominent member of the Sydney Jewish Community, as a founding member of the Australian Jewish Historical Society and its Honorary Secretary from its inception in 1938 until his death, as a member of the Board of Management of the Great Synagogue, Sydney for 25 years and as a councillor of the NSW Jewish War Memorial. Ben was followed to SBHS, by then at Moore Park, by his sons Harold (1930 to 1934) and Ken (1934 to 1938).

Harold represented the School in debating and rugby, captaining the 2nd XV in 1934. The Jubilee Record (October, 1933) reports on the Senior Debating Team and says of Harold: “Clear, lucid, deliberate speaker; pleasing personality; with a little experience, should go far.”  Harold was appointed a prefect in 1934. Harold won a number of academic prizes at SBHS, including the Earle Page Prize for Modern Languages (shared) in 1934. In the 1934 Leaving Certificate, he obtained Honours in German (coming first in the State), Latin and French, and was awarded a University Exhibition. He attended Sydney University, graduating in Arts, with First Class Honours and shared the University Medal in Philosophy, and in Law, again with First Class Honours and sharing the University Medal. During World War 2, Harold joined the Royal Australian Navy, attaining the rank of Lieutenant. He served on ships and shore installations, in Australia and New Guinea, principally as a coding and cypher officer. 

After the War, Harold practised as a barrister in Sydney, becoming a Queens Counsel in 1962. In 1973 he was appointed a Judge of the Supreme Court of NSW and in 1974 a Judge of the NSW Court of Appeal, where he served until he retired in 1987. Harold had returned to the Navy in the 1960’s as a member of its Legal Panel. In 1969, he was the Navy’s leading counsel in the joint Australian and USA Navies’ Board of Enquiry into the collision between the Australian aircraft carrier HMAS Melbourne and the US destroyer USS Frank E Evans in the South China Sea. Harold became the Judge Advocate-General for the Navy, attaining the rank of Rear Admiral.   Harold was appointed an Officer of the Order of Australia in 1988 for services to Law and the Royal Australian Navy. Harold died in 1989.

Ken represented the School in rugby, swimming and athletics, and was a member of the 1st XV in 1938. He too won academic prizes at SBHS, including the K Saxby Prize for Mathematics and Physics, 4th Year in 1937. In the 1938 Leaving Certificate, Ken obtained honours in Mathematics and was awarded a University Exhibition. He attended Sydney University, graduating in Arts and in Law, with First Class Honours. During World War 2, Ken served in the Royal Australian Air Force, attaining the rank of Flying Officer. He was a member of a small group of young men, with demonstrated skills in mathematics and physics, who were specially trained in radio physics and the new technology of radar, followed by roles in the development, installation and maintenance of radar and radio equipment, in aircraft and on land, at different locations in Australia, principally Charters Towers, Queensland, where there was a large RAAF base.  After the War, Ken practised as a solicitor in Sydney until he retired in 1988. He died in 2001. Ben’s daughter Aviva attended SGHS, attaining the Leaving Certificate in (we believe) 1942.

The next generation at SBHS was Ken’s son, Jeremy (1965 to 1970). Jeremy represented the School in rugby, acted as an instructor in life saving  and was a member of the Cadet Unit, attaining the rank of Cadet Under Officer. He was a student editor of The Record in 1969, and was appointed a prefect in 1970. In 1969 he shared the Arch Ferguson Prize for 5th Form. Jeremy graduated in Law from the University of NSW and has practised as a solicitor in Sydney since 1977. From 1977 to 1988 Ken and Jeremy practised law together, as partners from 1979 until1986.  Ken’s daughter Penny attended SGHS from 1969 to 1974.

The fourth generation at SBHS were Jeremy’s sons Tim (1996 to 2001) and Ben (1999 to 2004). Tim represented the School in rugby and rowing, and was a member of the 1st VIII in 2001. In 2000 he was awarded the Arch Ferguson Prize for Year 11. After leaving SBHS he coached School rowing crews for several years. Tim graduated from the University of NSW in Commerce and Science, with First Class Honours in Pure Mathematics. He subsequently attained a PhD in Mathematics from University of NSW. He works in risk with National Australia Bank. Ben also represented the School in rugby and rowing, and was a member of the 2nd VIII in 2004. In 2004 he was appointed a prefect and was awarded the Arch Ferguson Prize for Year 12. Ben graduated from Sydney University in Arts, majoring in Philosophy, and in Computer Science and Technology. He works as an application analyst at Sydney University.

Old boy fathers have the pleasure of reconnecting with the School when their sons attend it. While it is now not known how this applied to Ben (Senior) when Harold and Ken were students at the School, family legend has it that when Harold was in his early years at SBHS some mischief involving school lockers brought him to the attention of the Headmaster, Mr Saxby. Unfortunately for Harold, Mr Saxby had been a teacher at SBHS in Ben’s time and sent him a personal note regarding Harold’s misconduct in which he suggested that it warranted a severe “wigging”. This resulted in a father-son debate about whether or not this involved some degree of corporal punishment which, despite Harold’s later debating skills, was resolved to his disadvantage.   

When Jeremy attended the School, Ken enjoyed returning to McKay and other GPS grounds, where he had played, to support Jeremy’s teams, sometimes even catching up with other old boy fathers. He was again able to do so when Tim and Ben were there. In 2001, only a few months before he died, Ken attended the Head of the River, for the first time since 1938, to cheer on Tim in the 1st VIII. Jeremy also enjoyed his “second coming” at SBHS, thanks to Tim and Ben. Over the nine years covering their time at the School he spent many Saturdays at McKay, the Outterside Centre and other GPS rugby and rowing venues as a parent supporter, in addition to parent-teacher interviews and other school parent activities. Jeremy became a part of the SBHS rowing parents community and served on the Rowing Committee for five years, four as President. He was greatly honoured in 2004, after his term as President, to have a quad scull boat named after him.