Early Years
Olney was born into a family of means in Oxford, Massachusetts. His father was Wilson Olney, a textiles manufacturer and banker. Shortly after his birth, the family moved to Louisville, Kentucky, until Olney was seven. The family then moved back to Oxford and Olney attended school at the Leicester Academy in Leicester.
After completing his education there, he went to Brown University, where he graduated with high honors as class orator in 1856. He then attended Harvard Law School, where he received a bachelor of laws degree in 1858. In 1859, he passed the bar and began practicing law in Boston, attaining a reputation as an authority on probate, trust and corporate law.
In 1861, Olney married Agnes Park Thomas of Boston, Massachusetts.
He served as a member of the Board of Selectmen of West Roxbury, Massachusetts and in the Massachusetts House of Representatives in 1874, serving one term. He declined to run again, preferring to return to his law practice In 1876, Olney inherited his father-in-law's Boston law practice and became involved in the business affairs of Boston’s elite families. During the 1880s, Olney became one of the city’s leading railroad attorneys and the general counsel for Chicago, Milwaukee and St. Paul Railway.
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