Judge Day received his Bachelor of Arts degree from the University of Maryland in 1978, his Master of Science degree from The American University in 1980, and his Juris Doctorate degree from the University of Maryland in 1984.

After being admitted to the practice of law, Judge Day became a prosecuting attorney who successfully litigated several high profile cases in the Montgomery County State’s Attorney’s Office.  He later practiced law with the Washington, D.C. firm of Sherman, Meehan, Curtin, & Ain.  For many years, Judge Day was a frequent legal commentator for CNN and other national television and cable broadcasts.

Judge Day was appointed a United States Magistrate Judge for the District of Maryland, on February 18, 1997.  He is the first African-American Magistrate Judge for the District of Maryland, and the second person of color to serve in this position in the Fourth Judicial Circuit of the United States.  The Fourth Circuit includes the states of Maryland, Virginia, West Virginia, North Carolina, and South Carolina. 

Judge Day has held many positions of leadership.  He is a former Co-chair of the American Bar Association's Race and Racism in the Criminal Justice System Committee, and has served on the ABA Criminal Justice Section Council.  He has chaired the Maryland State Bar Association's Leadership Academy and the Alan J. Goldstein Inns of Court, and was Vice-chair of the Maryland State Court’s Commission on Racial and Ethnic Fairness in the Judicial Process. He is a Past President of the Federal Magistrate Judges Association and former Chair of the National Conference of Federal Trial Judges for the American Bar Association.

udge Day is an active member of many professional organizations and has served on the board of directors of a number of civic, charitable and Christian organizations, including Habitat for Humanity - Montgomery County Chapter.  Judge Day has been on several missionary trips to Romania to build churches, to Mexico and West Virginia to help build several homes for the needy, to Kenya to build walls around a facility for refugee women, and he travels yearly to the Dominican Republic as part of a medical/construction faith-based mission effort.  Judge Day and his wife, Cheryl, are the proud parents of three young adults.