It’s not exactly breaking news that fruit companies can have sordid passed, often with ties to colonialism or other dreadful nonsense like the Chiquita scandals in the 1990s. But the scurrilous history of of the founder of the Dole Food Company tends to come out of left field, especially since it has nothing to do with pineapples and everything to do with a rather disastrous airplane race.
James Dole was born in 1877 and earned the delightful nickname “The Pineapple King” for his career as America’s pineapple magnate, and there’s really nothing else I could tell you about him that could top that. But for context, I’ll tell you that he moved to Hawaii at the age of 22 with nothing but a dream and a bachelor degree in agriculture. He experimented with a variety of crops on his small Oahu farm before settling on pineapples, and as his farm and his worth continued to grow, he founded the Hawaiian Pineapple Company (HAPCO) in 1901. Inspired by Charles Lindbergh’s historic flight, Dole offered $25,000 for the first person to fly from California to Hawaii (a feat never before attempted) and so the Dole Air Derby was born.
The race was set to begin in Oakland, California, and pilots would be required to travel 2,400 miles over the Pacific to Honolulu, Hawaii. About a month after the reward was posted, the first transpacific flight took place. Actually the first two transpacific flights took place, the first by Army Air Corps pilots making a preplanned flight from Oakland Municipal Airport to Wheeler Army Airfield on Oahu after nearly 26 hours in the air and the second by two civilians who also departed from Oakland Municipal Airport but crash-landed in Molokai. Dole disqualified both flights for not landing in Honolulu. In August, two Navy pilots died in a plane en route to Oakland to begin the race and the next day, a stunt pilot making a test flight before starting his own journey to Hawaii also died in a crash, marking the start of a tragic series of attempted record-breaking flights.
The race officially began on August 16, 1927, with a lineup that had been diminished (by fatal and non-fatal crashes involving potential entrants) to eight planes: Livingston Gilson Irving’s Pabco Flyer, Arthur Goebel and William Davis Jr.’s Woolaroc, Bennett Griffin and Al Henley’s Oklahoma, Martin Jensen and Paul Schluter’s Aloha, Norman Goddard and Kenneth Hawkin’s El Encanto, Jack Frost and Gordon Scott’s Golden Eagle, Auddy Peglar and Vilas Knope’s Miss Doran (named for its passenger Mildred Doran), and William Portwood Erwin and Alvin Eichwaldt’s Dallas Spirit.
The Oklahoma was the first to depart, flying off into the fog and heavy rains at 11 am. The crew quickly abandoned the flight and landed safely when the engine overheated over San Francisco. The next to depart was El Encanto, which swerved off the runway and crashed without ever leaving the ground, thankfully with no casualties. Pabco Flyer made it barely a mile from the airport before it too crashed, also without casualties, and the pilot abandoned the race after crashing again on the second takeoff attempt. Miss Doran made it off the ground, but quickly circled back and landed ten minutes later. Its second attempt, as well as the first takeoff attempts by Golden Eagle, Aloha, and Woolaroc, were all successful. Dallas Flyer also made it off the ground, but promptly circled back to land with significant portions of the fabric covering its fuselage ripped off. At the end of the day, only half of the contests had actually managed to begin the race.
26 hours and 17 minutes later, the Woolaroc landed successfully in Hawaii, earning its pilot and navigator the $25,000 grand prize. Two hours later, the Aloha claimed the $10,000 second prize. The other two planes — Miss Doran and Golden Eagle — were never seen again. Three submarines aided in the unsuccessful search for the downed craft and their five total passengers, and the newly-repaired Golden Eagle and its two crew were also lost over the Pacific during the search efforts, bringing the race’s casualties to seven, not including the three people who perished in attempts to reach Oakland for the start of the race.
Despite the tragedies, the race did have one positive outcome — it paved the way for transpacific air shipping, which meant that business for the Hawaiian Pineapple Company got quite a boost. However, the resulting drop in the price of pineapples and the Great Depression forced Dole to sell majority shares of his company to Castle & Cook. He was forcibly removed from leadership of the company in 1932, and when he died in 1958, one year before Hawaii became a state, he was buried on a hill overlooking the vast expanses of land that had once been his pineapple plantation.