Freelander was born in Sydney.[3] His father Selwyn was a dentist and president of West Harbour RFC,while his mother Ruth was a preschool teacher. Freelanders family has had a long history with the Labor party with his father being friends with former Prime Minister Ben Chifley. His paternal grandfather William Freelander arrived in Australia as a cabin boy and became mayor of Katoomba and the City of Blue Mountains.[4] Freelander attended Trinity Grammar School from 1965 to 1970,playing cricket and rugby and being appointed a prefect of the school. In the Higher School Certificate he qualified to study medicine at Sydney University.
Freelander became the head of Paediatrics at Campbelltown Hospital from 1986 to 2013.
Freelander needed to resign from his job in order to satisfy Section 44(iv.) of the Constitution,which prohibits a person holding any office of profit under the Crown from becoming a member of parliament.[6]
After being elected in 2016,Freelander has continued to volunteer at Campbelltown Hospital,[7][8] seeing both old and new patients from the Macarthur region. Freelander has seen over 200,000 patients over his medical career.[9][10]
Freelander has six children with his wife Sharon,[4] and had five grandchildren as of 2016.[2] He has said that he is "not a particularly religious Jew,but I still describe myself as Jewish".[5]
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