In 1894, Baldwin obtained a degree at the Massachusetts Institute of Technology, where he was a member of Chi Phi fraternity.

Haiku merged with the Pāʻia plantation, and he became president of the combined operation called the Maui Agricultural Company.

They had one daughter, Frances Hobron (1904–1996) who married J. Walter Cameron (1895–1976), manager of the pineapple plantation in Honolua.

[8] He was territorial senator until 1921 when he was called to higher office to fulfill the unexpired term of Prince Jonah Kūhiō Kalanianaʻole in Washington, D.C., who had died.

Following a single term, Baldwin returned to the upper chamber where he became territory senate president in 1937.

[11] The 1917 mansion designed by his cousin architect Charles William Dickey called Kaluanui is now the home of Hui Noʻeau Visual Arts Center.