Campus Director Brookland Campus & Director of Student Support


Bobby Caballero, better known as “Mr. Bobby”, was born in Havana, Cuba and raised in Los Angeles, CA. He left sunny southern California to attend Howard University, where he studied Human Development. While at Howard University, Bobby served as the Director of Howard University Student Association (HUSA) Big Brother’s Big Sister’s Program.  Early in his career Bobby was a youth organizer. He worked at Center for Community Change teaching youth organizers to advocate for themselves. It was working with a variety of youth, including incarcerated youth that lead him to work directly with education and educational administration.


Bobby joined the Stokes School family in 2001 as the Dean of Students when there were only about 80 students enrolled in the school. He was also the fifth and sixth grade Science and Social Studies teacher. He is proud of the programs and partnerships he has helped to develop over the years. Bobby is currently a Leading Educators Fellow. In 2014 he had the honor of speaking about “How to Create a Positive School Climate” at the U.S. Department of Education Charter Schools Program meeting of Project Directors.


Bobby is the proud father of a current Stokes Scholar.  He enjoys traveling, cycling, cooking, and spending time with his family.