Dole attended Roxbury Latin School and Harvard University. He graduated from Harvard in 1899.
In 1899, Dole headed for Hawaii with $1, 500 and an interest in agriculture. His ancestors had been traders and missionaries to Hawaii in the eighteenth century and his father's cousin, Sanford Dole, was about to become the first governor of the new United States territory. In 1900 Dole bought a government homestead of sixty-four acres at Wahiawa and began to grow vegetables and pineapples. Previous attempts to grow pineapples commercially had failed because a pineapple picked green is sour and tough, and will not ripen, whereas a ripe pineapple would spoil before reaching markets on the mainland. Dole decided to pick the fruit ripe, can it on the island, and ship it to the mainland.
In the spring of 1901, Dole planted 75, 000 pineapples, and in December of that year he organized the Hawaiian Pineapple Company. The first pack, canned in 1903, consisted of 1, 893 cases. The next year the cannery packed 8, 810 cases, and the next 25, 022. In 1906 the company earned $30, 489. Then came the panic of 1907, and the market for pineapple dried up. The Hawaiian pineapple industry, which by then consisted of eight packers, began 1908 with the prospect of a large, unmarketable surplus. Under Dole's leadership the members of the industry formulated a marketing plan unique in American business at the time - an industry-wide advertising campaign, without regard to brand. Within eighteen months the consumption of Hawaiian pineapple quadrupled.
In 1911 Dole hired Henry Ginaca to design a high-speed peeling and coring machine. Within a year Ginaca developed a machine that could size, peel, core, and cut the ends from 100 pineapples per minute. This made possible mass production of canned pineapple. Dole continued to seek ways to improve production and quality, and each new machine or technique was shared with the entire industry. Motor trucks, Caterpillar tractors, iron sulfate spray, and paper mulching were innovations he brought to pineapple growing. By 1916 he had leased 3, 676 acres of land from the Waialua Agricultural Company. Needing still more land, in 1922 Dole bargained with Waialua for 12, 000 acres on a seventeen-year prepaid lease with the right of renewal. For the lease and $1. 25 million in cash he gave Waialua one-third ownership of his Hawaiian Pineapple Company. With the cash he bought the island of Lanai for $1. 1 million. This cactus-covered land proved ideal for growing pineapples. Dole built a harbor, roads, and a town. Soon his company was producing 35 percent of Hawaii's pineapples.
Although not yet using his name as a brand, Dole was fast becoming the king of the pineapple industry. When Charles Lindbergh made his historic flight across the Atlantic in 1927, Dole became excited about the possibility of air service from Honolulu to the mainland. The Honolulu Star-Bulletin suggested an air race from California to Honolulu, and Dole offered $35, 000 as prize money. In August 1928, Art Goebel and William V. Davis, Jr. , won first prize. Because seven lives were lost in the effort, Dole was criticized for inspiring a dangerous stunt; but federal authorities, not Dole, had established the rules governing the flight.
As a result of the Great Depression, the Hawaiian Pineapple Company lost $5. 4 million in operating income in the first nine months of 1931 and was on the verge of bankruptcy. Dole had recently perfected new methods of manufacturing a better pineapple juice and hoped this would rescue his company; but time and money for promotion were lacking. When the company's board met in late 1932, it appointed a committee including three executives of Castle and Cooke, a corporate conglomerate that owned a substantial interest in the Waialua Agricultural Company, to work out a plan for reorganization. In December 1932 Castle and Cooke took over management of the new company. Dole was made chairman of the board, an honorary position that left him without effective authority. He naturally was dissatisfied with the arrangement and pointed out that at the same time his authority in the company ended, the Dole name first appeared on every can produced by the company. In 1933 Dole served briefly in Washington as chief of the Food Products Section of the Agricultural Adjustment Administration (AAA). Disillusioned with New Deal attempts to manage the economy, he resigned in January 1934, and in a series of articles condemned the inefficiency and conflicting authority he had found in the AAA.
Dole then moved to San Francisco, keeping his home in Hawaii primarily for vacations. He launched a series of successful new business endeavors with various partners. In 1936 he organized the Chemical Process Company to manufacture ion exchange materials for improved sugar purification. This company became a leader in its field and merged profitably into the Diamond Shamrock Company. Two years later Dole acquired the Schwarz Engineering Company, later renamed the James Dole Corporation, to develop food-processing equipment and techniques. A joint venture of this company and S&W Fine Foods resulted in a new product called Liquid Apple. Dole resigned as chairman of the board of the Hawaiian Pineapple Company in 1948. He continued, however, to receive remuneration for the use of his name.
By the time of his death, which occurred on May 14, 1958, in Honolulu, pineapple was contributing $116 million a year to the Hawaiian economy and the islands were producing 72 percent of the world's supply.
On November 22, 1906, Dole married Belle Dickey. They had five children: Richard Alexander Dole, James Drummond Dole, Jr. , Elisabeth Dole, Charles Herbert Dole, and Barbara Dole.