The Terrifying Death Race Sponsored By Dole Pineapples

“I feel sure that we will win, but if we don’t—well, life is just a game of chance anyway.” —Mildred Doran, before starting the race to Hawaii

In A Nutshell

In 1927, deranged pineapple tycoon James Dole, who had turned an entire Hawaiian island into the world’s largest plantation, announced that he would offer a $35,000 cash prize to the winner of an airplane race between California and Honolulu. No one had ever flown to Hawaii before, and it was clearly dangerous to attempt it in such primitive planes. By the time the race was over, 10 people would be dead.

The Whole Bushel

In 1927, James Dole, “the Pineapple King,” was on top of the world. Controlling the entire Hawaiian island of Lana’i, he produced an estimated three-quarters of the world’s pineapples. Dole was something of a technology buff. In 1913, his company had developed a machine that could peel 100 pineapples a minute—and he was enthralled by the possibilities of air travel. He wasn’t the only one. Charles Lindbergh had recently completed his famous flight across the Atlantic and America was crazy for the airplane.

So, that year, Dole announced that he would offer a $35,000 cash prize for an air race between California and Honolulu. There was just one problem: Nobody had ever flown to Hawaii before. The distance was almost as long as Lindbergh’s flight, the conditions arguably worse, and the small islands would be much harder to find than the continent of Europe. Experts cautioned that a race wasn’t the best way to attempt such a dangerous journey, but Dole ignored them.

The huge prize money attracted a ragtag mob of adventurers and daredevils. There was the legendary Hollywood aerial stuntman Art Goebel, who charged $80 to film a parachute jump and $15,000 to blow up a plane in midair. Then there was Mildred Doran, a young Michigan schoolteacher whose flying jacket was covered in fraternity pins from admiring suitors. William Randolph Hearst’s son hired a pilot named Jack Frost to fly for him, while the popular cowboy actor Hoot Gibson entered his triplane Pride of Los Angeles. Legendary World War I flying ace Captain William Erwin was hotly tipped, while Hawaiian local favorite Martin Jensen only managed to enter after his wife rallied the citizens of Honolulu to buy him a plane. In gratitude, he swore to “make it or die in the attempt.” Most intriguing of all were two navy lieutenants in a “mystery monoplane.”

Article Continued Below

Things went wrong from the start. The “mystery monoplane” slammed into a cliff, ending up as a heap of burning wreckage on the beach below. Another entrant heroically crashed his stalling plane into the sea to avoid the crowd of spectators packed around his runway. (Amazingly, he survived). Mildred Doran was having mechanical troubles as well, which weren’t helped by the fact that she had previously thrown all her tools out of the plane because they were “weighing her down.” Her biplane disappeared at sea and was never seen again. Jack Frost also vanished—and then so did Captain Erwin when he nobly detoured to look for the missing.

Ultimately, the race was won by the stuntman, Goebel, with Jensen a close second. No one else finished the race. In total, 10 people died before or during the race. Heartbroken, Dole offered a $20,000 reward for the missing pilots, but no bodies were ever found.

In a final moment of irony, while Goebel and Jepsen shared the prize money, they weren’t the first men to fly to Hawaii: Two army pilots had pipped them before the start of the race.

Show Me The Proof

San Francisco Call-Bulletin: Pioneer Pacific Fliers Wrote Tragic Chapter In Air History
Soaring Skyward, by Claudine Burnett
Hawaii Aviation: Arthur C. Goebel
Jamaica Plain Historical Society: James Drummond Dole

Looking for our newsletter? Subscribe here!