Claudette Winstead laid the foundation for her successful career by earning a bachelor of science in psychology with a minor in business administration at Howard University in Washington, DC. She went on to secure a juris doctor from the John Marshall Law School in Chicago, Illinois. While there, Claudette M. Winstead II placed first in the American Bar Association National Negotiation Competition.

Over the course of her career, Claudette M. Winstead II has handled litigative and governance matters for multiple companies and law firms in Illinois and in Washngton DC. In 2018, she advised the US Small Business Administration and helped it distribute critical disaster assistance loans. She also expanded her professional capabilities with a certification to mediate legal matters in community, state, and district courts.

Ms. Winstead has been a member of the District of Columbia Bar since 1995. Outside of the office, she enjoys golfing, boating, and riding horses. She is also an avid aviation enthusiast.