Henry Perrine Baldwin, was born on August 29, 1842 in Lahaina, Maui. His father was American missionary Dwight Baldwin (1798–1886.) (He was named after Matthew LaRue Perrine (1777-1836), a professor at Auburn Theological Seminary.) After receiving his education at Punahou School, HP Baldwin undertook the management of a rice plantation, but the venture was not successful and in 1863 he turned his attention to the cultivation of sugar cane, working first for his brother, Dwight Baldwin, Jr, at Lahaina.
Waiheʻe sugar was managed by Samuel Thomas Alexander. Henry Perrin Baldwin took a ‘Luna’ (foreman) job with Alexander. (HP Baldwin and Alexander grew up together as kids in Lāhainā and became close friends.) Baldwin’s intended to earn enough money to enable him to go to Williams College to take a medical course. (His father was a physician.) His youthful ambition to be a doctor was never realized. Once launched in the sugar industry he continued in it, an increasingly important figure, for the remainder of his life. Baldwin was particularly successful as an agriculturist, a developer of plantations. In 1869, Baldwin and Alexander became business partners.