In 1996, Judge Tailor joined the Cook County State's Attorney's office as an Assistant State's Attorney; then, he was promoted to Deputy Supervisor in the Torts and Civil Rights Litigation Section. Prior to that, he was in-house counsel to the First National Bank of Chicago and an associate at the law firm of Chapman and Cutler. He graduated cum laude from Loyola University of Chicago School of Law in 1991.

As an attorney, Judge Tailor has litigated a variety of civil matters, ranging from medical malpractice, civil rights, constitutional law, and commercial litigation. Most recently, he was the member of a team from the State's Attorney's Office who argued before the United States Supreme Court.

Judge Tailor has been active in the Indian American community for several years. He was a board member IADO for three years and is a current member. He is also the immediate past president of Apna Ghar, a full service domestic violence agency serving the South Asian community in Chicago and its suburbs. He is also a member of the Asian American Bar Association.