Carlotta Stewart Lai (September 16, 1881 – July 6, 1952) was an educator and administrator in the Hawaiian public schools for four decades. She was the first African American school principal in Honolulu. Lai, an African American from New York, worked as a teacher and educational leader at a time when these occupations were largely closed to African Americans on the U. S. mainland, and she achieved professional success at a time when African Americans represented only 0.2 percent of the population of Hawaii.
Lai was born in 1881 in Brooklyn, New York to Thomas McCants Stewart and Charlotte L. Harris Stewart. She was the third child and the only daughter, and she attended public school in Brooklyn. Her brothers, McCants Stewart and Gilchrist Stewart, both became attorneys. Her father, Thomas McCants Stewart, was an attorney and writer in New York, who was also involved in party politics in the field of voting rights. Her mother was a graduate of Wilberforce University. Lai’s maternal aunt was Verina Morton-Jones, an physician, charter founder of the Brooklyn NAACP, and co-founder of the Urban League.
When she was 18 years old in 1898, she moved to Hawai’i with her father and stepmother. Her father decided to move the family to Hawai’i in hopes of furthering his legal career. He was able to develop his legal practice advocating for “all varieties of people in diverse Honolulu,” and helped draft Honolulu’s City Charter.
When her father left Hawaii in 1905, Lai remained and never again returned to the U.S. mainland. Despite not having her family with her in Hawai’i, Lai had a vibrant social life with close friends and involvement in activities such as dances, parties, baseball games, and vacations. Scholars postulate that this social involvement, along with her professional progress and ability to “reside openly in an integrated community,” may have been some reasons why Lai decided to remain in Hawai’i.