He was appointed to a position in the United States Land Office from 1849 to 1852; he then resumed the practice of law in McConnelsville, Ohio, in 1853.

During the American Civil War, Tipton was appointed chaplain of the First Regiment, Nebraska Volunteer Infantry 1861–1865.

Full six feet in height, straight as an arrow, with long brown hair combed back from his forehead till it touches his coat collar, a pair of eyes that never look, but always glare or stare, and seem ready to jump from their sockets through the gold-rimmed spectacles in front of them, when their owner gets excited, which occurs every time he speaks in debate; a low forehead, a sharp nose and a mouth and chin which tell of bull-dog courage and determination, these, and the matter and manner of his speeches in the Senate, remind the student of history of what might have been the leader of the Barebones Parliament two hundred years ago.

"[1] Tipton had been elected as a Republican and voted for the conviction of President Andrew Johnson in the 1868 impeachment trial.

Endorsing the Liberal Republican movement and favoring Horace Greeley for president that year, he effectively read himself out of the party.