Esmonde was born 15 December 1893 at Pontesbury, Shropshire, England, eldest among three sons and three daughters of John Joseph Esmonde MP, a medical doctor who practised for twenty-four years in England before returning to family lands at Drominagh, Borrisokane, County Tipperary.
[2] On the death of his father in 1915 during service with the Royal Army Medical Corps in World War I, he was elected in the by-election in his place (opposed by two nationalist contenders) as Irish Parliamentary Party MP for North Tipperary while also serving in the war with the Leinster Regiment, then as Captain with the Royal Dublin Fusiliers with the Intelligence Corps.
He was defeated in the 1936 Wexford by-election to fill the vacancy created by the death of the sitting TD, his second cousin Sir Osmond Esmonde.
He subsequently served as a Fine Gael Teachta Dála (TD) for the Wexford constituency, where he won a seat at the 1937 general election.
In 1948, before the formation of the First Inter-Party Government, he was suggested as possible Taoiseach by Seán MacBride, on the grounds that he had no link to either side in the Civil War, a position that went to John A.
His younger brother Lt. Geoffrey Esmonde (1897–1916) aged 19 was killed in action in World War I serving with the 4th Tyneside Irish Battalion of the Northumberland Fusiliers.