Reilly, a native of Springfield, Massachusetts, described himself as a "misguided youth" the year his father, Mortimer "Murty" Reilly, was found deadat home from a heart attack when Reilly was 16. Reilly was arrested for public drunkenness when he was 20. By age 22, he was focused with driving ambition, much to the credit of his friend Wayne Budd's father, an ex-Marine turned policeman in Springfield who took him under his wing and encouraged him to go to school. Reilly attended Cathedral High School in Springfield, Massachusetts. He graduated in 1959. After graduating high school, he went off to college in Nova Scotia at St. Francis Xavier University. He stayed there only a year, transferring to American International College in Springfield, Massachusetts, where he graduated on June 7, 1964. He received a Bachelor of Arts in Economics. In July 1966, Reilly married Ruth Gammons, now a retired schoolteacher. The couple have three daughters: Leslie, Meaghan and Kyle. Reilly moved to Washington, D.C. and worked for two years with the Central Intelligence Agency. For one year, Reilly lived in Dearborn, Michigan, where he worked with the Ford Motor Company as a Labor Relations Representative until 1967. Reilly attended Boston College Law School and received his JD in June 1970. Reilly worked for two years as a prosecutor in the state Attorney General's civil rights division. He worked for four years as a Suffolk County prosecutor. In 1976, Reilly and Budd formed "Budd and Reilly", a Boston-based law firm. The firm became the largest minority-dominated firm in New England.
Political career
Reilly left the law firm in 1983 to work inMiddlesex CountyDistrict Attorney Scott Harshbarger's administration as First Assistant District Attorney. In 1990, Reilly was elected Middlesex County District Attorney. He was reelected for a second term. Reilly ran for attorney general in 1998 against state SenatorLois Pines and won the Democratic Primary. He defeated Republican Brad Bailey in the November election. He was reelected for a second term in 2002. On November 30, 2005 Reilly said that he was conducting an investigation of Sony BMG over their use of the XCP Digital Rights ManagementDRM on Sony audio CDs. See 2005 Sony BMG CD copy protection scandal. In January 2006, Reilly came under fire for allegedly impeding an investigation into an October 2005 automobile crash which left two Southborough, Massachusetts teens dead, and another teen injured. Reilly has come under fire from gun rights advocates for allegedly abusing his regulatory authority for political purposes. On January 24, 2006, Reilly officially kicked off his first gubernatorial campaign in Springfield at his alma mater American International College. He finished third in the primary on September 19, 2006. His opponent, Deval Patrick, went on to win the general election.