James was born at Kyneton, VIC on the 4^th of January 1890⁽¹⁾ to Timothy O'Leary and Mary Ann Woods. James had a brother, Thomas (KIA), who is also remembered in the Avenue.

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James first enlisted at Bendigo in the AIF, 14^th Battalion on the the 19^th of October 1914, giving his age as 23 years and 9 months⁽¹⁾, but was discharged in December - medically unfit. On the 5^th of February 1915 he re-enlisted in the AIF, 21^st Battalion, C Company and gave his age as 23⁽¹⁾. James embarked aboard the HMAT A38 Ulysses in May, disembarking in Egypt in June.

James landed at Gallipoli in early September - however on the way the battalion's transport was torpedoed near the island of Lemnos and had to be abandoned. He was admitted to hospital for a week suffering from rheumatisim in November and then again in December before returning to Egypt in late December and again hospitalised for a few days in February 1916. In mid February James forfeited one days pay for being AWL for a day before being admitted to the 3^rd Auxiliary Hospital, Cairo a month later - dysentery, mild.

In August 1916 James rejoined his unit in France but two months later was again in hospital and a month later admitted to the Military Hospital, Gravesend. England - dysentery. James was classified as permanently unfit for general service in October 1917 and embarked for home aboard the Thermistocles in November, returning to Australia at the end of December and was discharged from the AIF in February 1918.

James enlisted at Kyneton, VIC, in the Australian Army in June 1940 - V1115 - however he was discharged in July of the same year.

James O'Leary died in Bundoora, VIC in 1961, aged 71.

He is listed on the Bacchus Marsh & District Roll of Honour.

Notes

1. On his first enlistment in October 1914 he gave his age as 23 years and 9 months and on his second enlistment in 1915 he gave his age as 23, however in his WW2 service records his date of birth is given as 4/1/1890.