Ann Caroline McMichael Calabrese was born in New Orleans, Louisiana, where she spent her early childhood. Later, her family moved to McLean, Virginia. She attended Thomas Jefferson High School for Science and Technology in Alexandria, Virginia, and completed a molecular biology and biotechnology mentorship program at the Food and Drug Administration in Bethesda, Maryland, working on a project to develop a Leishmaniasis vaccine. Mrs. Calabrese graduated from the University of Virginia in 2011, and the William & Mary Marshall-Wythe School of Law in 2014. She served as a post-graduate fellow at the Norfolk City Attorney’s Office from 2014 to 2015. From 2015 to 2016, she served as a judicial law clerk at the Portsmouth Circuit Court, Third Judicial Circuit in Portsmouth, Virginia for the Honorable Judges Johnny E. Morrison, William S. Moore, Kenneth R. Melvin, and James C. Hawks. Ann Caroline lives in Norfolk, Virginia and is an Associate Counsel for the Department of the Navy, Military Sealift Command. She works primarily on the acquisition of time and voyage charter contracts and operation and maintenance contracts, providing legal advice on both federal acquisition law and maritime law. She also litigates bid protests and contract claims. She lives with her husband Louis, a submarine officer, their three children, Louis, Mary, and Caroline, their two Great Pyrenees, and a cat named Omaha.