Carlotta Stewart Lai (September 16, 1881 – July 6, 1952) was an educator and administrator in the Hawaiian public schools for four decades.

[6] 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.

[8] Lai's maternal aunt was Verina Morton-Jones, a physician, charter founder of the Brooklyn NAACP, and co-founder of the Urban League.

[6] 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.

[6] 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.

[10] In 1909, when she was 28 years old, Lai was principal of Ko'olau Elementary School in Kauai, where she taught children from many different races and ethnic backgrounds.