[1] He attended Davidson College before reading law for 2 years in the offices of Richmond Mumford Pearson, Chief Justice of the North Carolina Supreme Court.

Though, himself, a Democrat, in 1901 Osborne defended both North Carolina Supreme Court Chief Justice David M. Furches and North Carolina Supreme Court Associate Justice Robert Martin Douglas during their impeachment hearings.

Osborne was of the opinion that the Republican judges' impeachments were unwarranted and an attempted political purge.

Osborne's brilliant speech before the North Carolina General Assembly in closing defense of the justices caused both to be acquitted.

As reward for his successful defense of the justices, Theodore Roosevelt upon assuming office as President of the United States appointed Osborne a judge of the United States Court of Private Land Claims, on which he served from 1901 to 1904.