Professor Dortch-Okara was associate justice of the Massachusetts Superior Court, a position she held for 23 years before retiring in 2012. In 1998, Judge Dortch-Okara was appointed by the Supreme Judicial Court to serve as the chief administrative justice of the Massachusetts Trial Court. She was the first African American and the first woman to hold that position. Appointed to the bench in 1984, she served as justice of the Boston Municipal Court for five years, where she was instrumental in launching an alternative sentencing program for women. Formerly she held positions as associate general counsel of the Massachusetts Port Authority, attorney adviser for the Massachusetts office of the U.S. Department of the Interior, and assistant corporation counsel for the City of Boston. She received the Massachusetts Black Lawyers Association's 2011 Trailblazer Award, the Massachusetts Academy of Trial Attorneys' 2007 Judicial Excellence Award, and an honorary doctor of laws degree in 1996 from New England Law. She teaches The Law and Ethics of Lawyering and Criminal Law.