In 1923 he married Freida Helene Josephine Buddee in Newtown. She remarried in 1943.
Gerald died from a workplace accident in 1929 at the age of 30. His father, George, had died six years earlier. His mother did not die until 1955.
An inquest was held and determined the following cause of death:
Injuries accidentally received through being knocked down by a sleeper railway train when engaged in shunting operations.
Central Rly Station. Sydney.
Name: Gerald Cashel O'Brien
Birth Year: abt 1899
Birth Place: Golspie, N S Wales
Death Year: Abt 1929
Death Place: Central Rly Station
Sydney Inquest Date: 17 Jun 1929
Inquest Place: Sydney
Age: 30
Gerald is buried at Rookwood Cemetery next to his father and grandfather - SEC*M2*2**203.