In 1898, Carlotta Stewart, at eighteen years of age, came to Hawai‘i with her father (probably at his urging,) to continue her education and to begin planning her future. (Guttman)
The third child of Thomas McCants Stewart and Charlotte Pearl Harris, Carlotta was born in 1881 in Brooklyn, New York, where she attended public schools during her formative years.
Although her father had spent several years in Liberia, Africa, Carlotta had never traveled outside of the continental United States before coming to Hawai‘i.
Her father – a noted black lawyer, civil rights leader and friend of Booker T Washington – was the first African American to be admitted to practice law in Hawaiʻi (1898.) (jtb-org)
She attended Oʻahu College (Punahou,) where she played on the girls’ basketball team. After she graduated from there, she continued with basketball, playing for the YWCA and serving as timekeeper for the local games.
Her brothers McCants and Gilchrist had attended Tuskegee Institute, the Southern vocational school established by Booker T
Washington (1881,) Carlotta lived with her father following a bitter divorce from his first wife. (Broussard)
She graduated from Oʻahu College in 1902, one of eight members in the senior class. The course of study there included classes in philosophy, religion, English, Latin, Greek, French or German, history, economics, mathematics and science.
After graduation, Carlotta completed the requirements for a Normal School certificate (later known as the Teachers’ College,) which she received in 1902, and she promptly accepted a teaching position in the Practice Department of the Normal School.
She had converted to Catholicism during the early-1900s, despite the fact that her father was an ordained minister in the African Methodist Episcopal Church and that she visited the Priory (an Episcopal school) often as a young teacher to pray, study and dine with other females. (Broussard)
Stewart remained at the Normal School for several years, where she taught English; she is listed in the Report of the Superintendent of Public Instruction to the Governor of the Territory of Hawaii between 1902 and 1924.
Her father and stepmother left the Islands in 1905; Carlotta later noted “Sometimes I get quite blue not having a single relative in the Islands. … I soon get over it, for I have such good friends. I want for nothing.”
In 1906, in addition to teaching, she was busy with classes, vacations, camping, surfing and frequent parties. “We took in two dances a week at the Seaside Hotel and played cards at home the other evenings or made up moonlight bathing parties.” (Stewart; Broussard)
In 1909, Carlota was noted as a teacher assigned to Koʻolau Elementary School (Kauai,) a later newspaper story noted that she was identified as principal there. “This school (is) situated on the government road near the north side of Moloa‘a Valley, between Anahola and Kilauea”.
Initially, total enrollment for the school was 61, average attendance 59; Japanese 31, Part Hawaiian 19, Hawaiian 7 and Portuguese 4.
“The majority of the children here come from the homes of the small tillers of the soil in the Moloa‘a Valley and thereabouts, especially the rice fields of the Japanese and the kuleanas of the Hawaiians.” (Evening Bulletin, October 14, 1909)
Her rapid advancement in the space of seven years was an impressive achievement, although many black women had established teaching careers and a handful were school administrators by 1909, it was unusual for a black woman at the age of 28 to serve as principal of a multi-racial school.
This achievement was particularly striking in a society in which few black people lived and, therefore, had no political influence to request a job of this magnitude. Her pupils reflected a true cross section of Hawaii’s school-aged population, which grew rapidly between 1900 and 1940.
Conditions were neither difficult nor racially oppressive for a black professional woman, in Hawai‘i, there was no substantial black community before World War II, and Carlotta saw few black people either in classrooms or outside.
Most of her socializing took place in groups, relieving her of the pressure to find a companion with a comparable racial and social background.
She met and married her husband, Yun Tim Lai of Chinese ancestry at Anahola. He was sales manager of the Garden Island Motors, Ltd, an automobile dealership in Lihue, when the couple wed in 1916. (The 19-year marriage ended, however, in 1935, when Lai died suddenly in Hong Kong while visiting his parents.) (Broussard)
Carlotta Stewart Lai never remarried but remained in Hawai’i for the next 17 years, serving as principal and English teacher until her retirement in 1944.
By 1951 Lai’s health grew increasingly more fragile, and, unable to provide for herself without fear of bodily injury, she entered the Manoa Convalescent Home in 1952 and died there on July 6, 1952.