 Westropp Bennett was educated at Kilkenny College, where he was a contemporary of Admiral of the Fleet, the 1st Earl Beatty (later First Sea Lord of the Royal Navy during World War 1) and the Queen's Service Academy in Dublin but, unusually, did not attend Trinity College, Dublin where many of his ancestors had studied.On completion of his education, he returned to the Bennett family's extensive landholdings in Limerick and both farmed and took a prominent role in County Limerick life.As a magistrate he was active in local government as a district and county councillor and stood for the Westminster Parliament at the January 1910 general election as an Independent Nationalist in West Limerick, with the support of the All-for Ireland League, a non-sectarian alliance of nationalists and unionists, where he came within 70 votes of winning the seat in a close fought contest.