James Dole was born on September 27, 1877, in Jamaica Plain, Massachusetts (now part of Boston), to an American Puritan family long settled in the country since colonial America times.

Soon, yields and popularity of his product proved greater than he expected and Dole built a new cannery and packing plant near Honolulu Harbor.

In 1913, Dole invested in a new machine invented by Henry Gabriel Ginaca that could peel and core 35 pineapples every minute.

Before the invention, Dole had to contend with the slow pace of having hundreds of workers peel and core each pineapple by hand.

Rival pineapple companies slowly began to adopt the Ginaca machine, seeing how much Dole improved his business with the introduction of new technologies.

[citation needed] By 1922, Dole had managed to convince his family's network in Hawaii and in Boston to arrange for a sizable capital investment fund with which he purchased the island of Lānaʻi and developed it as a vast pineapple plantation.

Utilizing large mechanized production and importing large numbers of foreign workers who were paid at indentured servitude levels, Dole managed to reduce the price of his pineapples to such a level that it drove every other producer out of the business which didn't fall into line with his scheme.

The largest competitors in the production of pineapple in Hawaii were Maui based affiliates of Alexander & Baldwin.

In 1927, inspired by Charles Lindbergh's successful trans-Atlantic flight, and seeing the potential air transportation could play in delivering his fruit, thereby making an end-run around what remained of his competitors in the Alexander & Baldwin affiliated Matson Navigation Company, Dole sponsored the Dole Air Race, putting up a prize of US$25,000 for the first airplane to fly from Oakland, California, to Honolulu, and US$10,000 for second place.

Because pineapples take two years to grow to maturity, the Great Depression of the 1930s and the resulting decrease in demand caused the company to lose money.

In 1989, the fruit stand was transformed into a plantation home mounted on what looks like a hill of red dirt, characteristic of Wahiawa.

[13] In 1991, the Dole Cannery closed its operations and was transformed into a multi-purpose facility with media studios, conference rooms and ballrooms.

The lower levels houses a modern shopping center and an 18-screen multiplex cinema owned by Regal Entertainment Group.

The actual ginaca machines and cannery storage were preserved and turned into a museum of Hawaiian Pineapple Company history.