After leaving home at the age of 22, Leedy spent the next three years mining and railroading. He returned to the family farm when he was about 25. On 27 March 1890, Leedy married Emma Cathrine Keister, a daughter of Martin and Elizabeth Keister. Shortly after marrying, the new couple relocated to
Basic City, Virginia. He engaged in a variety activities there, including real estate and mercantile pursuits, and he began to read law under D.S. Henkle, and in the offices of
Floyd Wise Weaver and
John B. Minor. Eventually entering the summer law school at the
University of Virginia, Leedy was admitted to the bar in
Augusta County, Virginia in September 1893. In the midst of his legal education, Leedy was elected mayor of Basic City. Reelected in 1894, Leedy resigned a year later and moved to
Luray, Virginia. A junior partner in the law firm of Weaver (Floyd Wise Weaver) and Leedy, he left the firm in 1899 to practice alone. In 1908, he partnered with Richard F. Berry and T.L. Benson to create the firm of Leedy and Berry. During his legal career, Leedy was particularly known for work on several cases pertaining to railroad damage suits. In 1914, Leedy was elected as a member of the
Virginia House of Delegates in the
Virginia General Assembly. Representing
Page County, Virginia and
Rappahannock County, Virginia, he held his seat for two terms. == Military service ==