Chester C. Cole graduated from Harvard Law School and practiced law in Kentucky after graduation. Upon moving to Iowa in 1857, he helped establish the University of Iowa College of Law. He served as a professor for ten years. He also helped establish what become Drake University Law School, where he served as dean until 1907. Cole Hall on Drake University's campus is named for Justice Cole.
He also served on the Iowa Supreme Court from 1864 until 1876, including one year as Chief Justice. Justice Cole authored the opinion in Clark v. Board of School Directors, 24 Iowa 266 (1868), holding that racial segregation in Iowa's public schools was a violation of the state constitution. He died in 1913.