He has practiced both as a government lawyer and in the private sector. While in private practice, he was a partner in the law firm of Brackey, Finkelstein and Dallas, and specialized in criminal defense. In 1987, Finkelstein's license to practice law was suspended after he pleaded no contest to drug possession and driving under the influence. Prosecutors also accused him of using his position as an attorney to obtain a court order that allowed him to retrieve drugs confiscated from a client.