James David Stewart was born 15 January 1874 in Lower Montague, Prince Edward Island to David Stewart and Lydia Ayers. He married Barbara Westaway and the couple had seven children.

Stewart received his early education in the local Montague school before attending Prince of Wales College in Charlottetown and Dalhousie University in Halifax, Nova Scotia. He taught school for a few years before entering the practice of law in Montague and Georgetown.

In 1917, Stewart ran in the Kings County by-election and won a seat in the legislature. In 1919 he was re-elected. He was elected leader of the Provincial Conservative party in 1921 and in 1923 he led his party to victory. As premier, Stewart was against total prohibition and his stand on the controversial issue is believed to have contributed to his defeat in the 1927 general election. In 1931, he was again elected as premier, making him the first party leader to become premier for a second time since Prince Edward Island had entered Confederation. In addition to the premiership he held a number of cabinet posts, and in the federal arena consistently fought for Maritime rights. He was successful in securing an increased subsidy for the Island from the federal government.

On 10 October 1933 James David Stewart died in office.