In 1988, Steward was hired by the Boston Red Sox as an associate counsel; she was promoted to assistant general manager in January 1990.[5][6] She became the first African American woman, and second female minority, to hold an executive position for a major-league baseball team.[7]
As of 1997, Steward and her husband, Chuck, had three children.[2]
Steward was selected as one of the "Ten Outstanding Young Leaders of Boston" by the Greater Boston Chamber of Commerce in 1999. She was also elected into the YWCA's Academy of Women Achievers. During her time at St John’s University, she received the Outstanding Alumna Award from the Black Alumni Association and the St. John’s University President’s Medal. Later on, she went on to receive the National Association of Black Journalists Sports Task Force’s Sam Lacy Pioneer Award, and the Jackie Robinson Foundation Sports Management award and scholarship.[4]