Kevin O'Brien is a 1975 graduate from the Suffolk University Law School, Boston, Massachusetts. He received his Bachelor of Arts degree in history in 1972 from St. Anselm College in Manchester, New Hampshire. In 1975, Kevin was an associate with the Law Firm of David M. Barry and became a partner in the firm of Barry & O'Brien in 1979. In 1990 Kevin joined Barry Botticello and Steve Penny, and in 2006, together with his brother, Bill O'Brien and Tom Robinson, created the law firm of Penny, Botticello & O'Brien, P.C. ​