Pickler was born in Salem, Indiana, and moved to Davis County, Iowa, in his youth.

He attended public schools in Davis and enlisted in the 3rd Iowa Cavalry Regiment during the American Civil War.

[3] While serving in the Dakota Legislature, he played a key role in introducing the territory's first bill to give women the right to vote.

After leaving Congress, Pickler resumed the practice of law, and also became active in the real estate business.

Pickler died on June 13, 1910, in Faulkton, South Dakota, at the age of sixty-six.