Judge Lindsay was born, raised and attended public schools in Birmingham, Alabama. In 1962, after completing the eleventh grade at Birmingham’s Carver High School, he was granted a Merrill Early Admission Scholarship to Morehouse College.

While at Morehouse, he was the recipient, in 1965, of an additional Merrill scholarship for travel and study abroad. With that scholarship, he studied for fourteen months at the University of Valencia, Spain. While in Valencia, Judge Lindsay also taught English as a second language at the Institute of North American Studies.

Judge Lindsay returned to Morehouse College in the fall of 1966 and graduated with honors in 1967. At Morehouse he was elected to Phi Beta Kappa and Pi Sigma Alpha, the National Political Science Honor Society.

In the fall of 1967, Judge Lindsay entered Harvard Law School. At Harvard, he was president of the Black Law Students Association. He graduated from Harvard in 1970.

In 1975, at the age of twenty-nine, Judge Lindsay was appointed by then Massachusetts Governor Michael S. Dukakis to the post of Commissioner of Public Utilities. He served in that office for just under three years and then returned to Hill & Barlow. In 1979, he became a partner at Hill & Barlow.

During the period 1983 to1988, Judge Lindsay was a member of the Massachusetts Commission on Judicial Conduct. He also served on the Council of the Boston Bar Association. During the period 1992 to 1993, he chaired a Boston Bar Association Task Force on the Massachusetts Juvenile Justice System. He was principal author of the Task Force’s report: The Massachusetts Juvenile Justice System of the 1990's: Rethinking a National Model, 1993, reprinted in 21 New England Journal on Criminal and Civil Confinement 339 (1995).

Judge Lindsay was appointed by President Clinton to the United States District Court for the District of Massachusetts in November, 1993.

He was frequently included in Best Lawyers in America, Who’s Who Among African Americans, Who’s Who in America, and Who’s Who in American Law. In 1994, he was recipient of the Ruffin-Fenwick Trailblazer Award, given by the Harvard Black Law Students Association. In1995, Judge Lindsay received the United Negro College Fund’s Outstanding Alumnus Award. In 1998, he received from Boston College its Amanda V. Houston Community Service Award. In 1999, the Boston Bar Association presented Judge Lindsay with its Citation for Judicial Excellence. Also in 1999, Easter Seals of Massachusetts presented Judge Lindsay with its Frederick E. Berry Expanding Independence Award. In January 2001, he was presented with the “Heroes Among Us” Award by the Boston Celtics. In February, 2001, he received the New England Black Law Students’ Leadership Award. In May, 2003, Judge Lindsay was awarded an honorary degree of Doctor of Laws by New England School of Law. In April of 2005, he was awarded the N. Neal Pike Prize, given annually by the N. Neal Pike Institute of Boston University School of Law to an individual who, despite a physical or mental disability, has achieved notable success. In 2007, Judge Lindsay was again a recipient of the Boston Bar Association’s Citation for Judicial Excellence, sharing the award with his colleagues Chief Judge Mark L. Wolf and Judge Patti B. Saris. Judge Lindsay was a member of the American Law Institute, the American, National, Massachusetts and Boston Bar Associations and the Massachusetts Conference of Black Judges. He was a fellow of the American Law Foundation and a member and former President of the Board of Directors of Partners for Youth with Disabilities, Boston. He also served on the Board of Directors of Morgan Memorial Goodwill Industries, Boston and on the Board of Directors of the West Suburban YMCA Newton, Massachusetts. He served for nine years as a trustee of the Newton-Wellesley Hospital, Newton, Massachusetts.