Born near Brevard, North Carolina, Henry Kimsey Osborne attended Furman University and Wake Forest University. He taught school in Greenville and Spartanburg counties for two years. He studied law privately, and was admitted to the Bar in 1898. He became the partner of Thomas B. Butler in Gaffney.
In 1908, he moved to Spartanburg and practiced there until 1945. He was an associate of Stanyard Wilson and a partner of Horace L. Bomar. In 1932, with namesake son of his Gaffney partner, he founded the firm which became Osborne, Butler and Moore, when joined by his son-in-law, Leon Moore.
He became an outstanding trial lawyer by complete, painstaking preparation of each case and diligent devotion to his clients’ causes, whether civil or criminal.
He served as an Assistant United States District Attorney from 1925–33 and as Spartanburg County Attorney. He was an Acting Associate Justice of the South Carolina Supreme Court and served in the South Carolina Legislature from 1911–13 and 1936–38.
A talented musician, he supported and enjoyed musical events. He was, lifelong, a strong churchman.