Thomas Harper Sheppard, II
Mr. Sheppard holds an undergraduate degree in Political Science from Wake Forest University and received his J.D. from the University of Baltimore School of Law in 2008. Thereafter, Mr. Sheppard spent two years as a law clerk for the Honorable Robert J. Humphreys of the Court of Appeals of Virginia. Following his clerkship, Mr. Sheppard served three years as an Assistant Commonwealth’s Attorney in the City of Norfolk, prosecuting hundreds of felony and misdemeanor cases in the Circuit and General District Courts. Since that time, Mr. Sheppard has been in private practice representing clients all over Hampton Roads in matters ranging from simple traffic offenses in General District Court to felony criminal charges in Circuit Court to complex appeals before the Court of Appeals and Supreme Court of Virginia. Mr. Sheppard’s background, experience, preparation and professionalism help him to attain the best possible outcome for his clients.
- University Baltimore School of Law – J.D. 2008
- Wake Forest University, Winston-Salem, NC – B.A. 2004
- 2018 – American Institute of Criminal Law Attorneys: “10 Best” in Exceptional and Outstanding Client Service
- 2019 – Attorney and Practice Magazine: “Top 10 Criminal Defense Attorney”
William H. (Happy) O’Brien
Born and raised in Virginia Beach, William H. “Happy” O’Brien grew up in the Great Neck area and graduated from Frank W. Cox High School. After graduating from Davidson College, near Charlotte, NC in 1996, he spent a year coaching at the College of William & Mary, then began his legal education at George Mason University. Following a year of study there, he transferred to the University of Virginia, and graduated with the class of 2000.
Upon graduation from law school, he began his career as an associate with Brydges, O’Brien & Frucci and gained the invaluable experience of learning the practice of law from Dick Brydges. After honing his skill as a courtroom advocate capable of handling criminal, civil and domestic matters, in 2005 he moved on to become a partner in the firm of Brydges, Geroe, Rosenblatt & O’Brien. The successful union allowed the firm to provide services as they relate to all aspects of traffic and criminal law, personal injury/medical malpractice and domestic law. Prior to the formation of the new team at Doummar & O’Brien in 2013, Happy was also recognized in Super Lawyers 2010 as one of the “Top Young Lawyers in Virginia.”
In addition to serving his clients, Happy enjoys community involvement through coaching area youth in a variety of spots in his hometown of Virginia Beach.
Alexandra E. Cruz
Alexandra Cruz comes to Sheppard & O’Brien with over 20 years of legal experience and specializes in the areas of criminal law, family law and estate planning. Alex handles felony criminal, corporate, estate planning and family law files for the firm. Her legal knowledge, excellent demeanor and upbeat personality have made her a valued member of our team of associates and partners.
Born and raised in Virginia Beach, Alex likes spending her free time with her daughter, family and friends.