The Dole Air Derby, the Pineapple King's Pacific Prize, and the Eight Planes That Left Oakland for Hawaii on August Sixteenth, Nineteen Twenty-Seven

On August 16, 1927, eight aircraft left Oakland Municipal Airport bound for Wheeler Field in Honolulu - 2,400 miles of open Pacific Ocean with no radio beacons, no alternates, and no realistic chance of rescue if an engine quit. Only two planes completed the crossing. The Dole Air Derby is one of aviation history’s most consequential tragedies, and one of its most important proofs of concept.

What Triggered the Race

Three months separated the Dole Air Derby from its real origin point. On May 21, 1927, Charles Lindbergh landed the Spirit of St. Louis at Le Bourget Field outside Paris, and the aviation world never recovered from the fever that followed. The Atlantic had been crossed solo. The Pacific was the obvious next question.

James Dole understood the question - and the opportunity behind it. Dole ran the Hawaiian Pineapple Company, known today as Dole Pineapple, and the constraint on his business was the same one that constrained everything between Hawaii and the mainland: distance. The steamship from San Francisco to Honolulu took four and a half days. A fast airplane, Dole calculated, could do it in under thirty hours.

In June 1927, Dole announced the prize: $25,000 for the first aviator to fly nonstop from Oakland to Honolulu, and $10,000 for second place. The rules were straightforward. Depart Oakland Municipal Airport. Land at Wheeler Field. The Dole Air Derby was open.

The Field That Assembled at Oakland

Fifteen aircraft eventually entered. That number tells you something about the summer of 1927. Some were properly equipped machines with experienced crews and capable navigation setups. Others were marginal at best - overloaded, under-navigated, and held together by mechanics who were working against a deadline more than a standard.

Aviation oversight in 1927 was still finding its footing. If you arrived at Oakland with an aircraft and something resembling a pilot certificate, you were a contender.

The derby turned the airport into a prolonged spectacle. Reporters arrived from every city on the West Coast. Photographers documented everything. Movie cameras rolled. Mechanics worked through the night drilling fuel tanks into fuselages and arguing about prop pitch, oil consumption, and wing loading. And before the race began, pilots started dying.

Norman Goddard and Arthur Donnelly were killed when their aircraft broke apart during a qualification flight over California. The crew of the El Encanto, a red-and-white aircraft, died in a test crash. The race had a body count before a single competitor reached the water.

Officials moved the start to August 16 to allow more preparation time, and airworthiness inspections were conducted with greater rigor. Several aircraft were disqualified as unfit for an open-ocean crossing. Eight planes were certified to start.

The Eight Crews

Art Goebel was 30 years old and had made his career as a Hollywood stunt pilot - the kind of work that means you know exactly where the edges are because you’ve professionally touched them. His aircraft was a Travel Air 5000 monoplane named the Woolaroc, sponsored by Oklahoma oilman Frank Phillips and named after Phillips’s ranch. Goebel’s navigator was U.S. Navy Lieutenant William Davis, who brought a sextant, a chronometer, an air almanac, and the systematic confidence of a man who had done the math and trusted it.

Martin Jensen, Danish-born and flying since 1917, piloted the Aloha with navigator Paul Schluter. Jensen was quiet with reporters. He just got ready.

The Miss Doran was piloted by Auggie Pedlar and navigated by Vilas Knope. It also carried a passenger: Mildred Doran, a 22-year-old schoolteacher from Flint, Michigan with no aviation experience. She had come aboard as a human interest story - a publicity figure the newspapers called the Flying Schoolmarm. She was cheerful, photogenic, and completely dependent on what was about to happen over that ocean.

Jack Frost and Gordon Scott flew the Golden Eagle, a Lockheed Vega with a clean monocoque wooden fuselage. Livingston Irving flew the Pabco Pacific Flyer. William Erwin and navigator Alvin Eichwaldt flew the Dallas Spirit.

The Start

Crowd estimates at Oakland Municipal Airport that morning reached ten,000 people. The morning coastal fog had cleared by mid-morning. A light wind came off the bay.

At noon, the starter’s flag dropped.

Goebel in the Woolaroc went first, lifting off with what witnesses described as unhurried certainty. He banked west over San Francisco Bay, climbed to altitude, and the Pacific took him. Jensen followed in the Aloha. Then the Miss Doran. The Golden Eagle. The Dallas Spirit. One by one, they turned west and disappeared.

The Crossing: Goebel and Davis in the Woolaroc

For Goebel and Davis, the crossing was twenty-six hours of relentless, grinding work. Davis bent over his charts as the sun dropped, shooting stars through his sextant when the sky cleared, computing positions by hand with tables, making small heading corrections. The math had to hold. A meaningful error over twenty-four hundred miles of featureless water meant flying past Hawaii until the fuel ran out.

Goebel held the Woolaroc below 2,000 feet to stay under the headwinds he’d been briefed about at altitude. The ocean ran black through the night, gray as the eastern sky softened, then blue as the sun climbed back up. The engine noise was constant - a reassuring roar that, after twenty-some hours, you stop hearing and start fearing the silence of.

Goebel put the Woolaroc down at Wheeler Field 26 hours and 17 minutes after leaving Oakland. Jensen and Schluter in the Aloha arrived 28 hours and 16 minutes after departure.

Two planes finished.

The Planes That Never Arrived

The Golden Eagle was gone. Jack Frost and Gordon Scott had left Oakland under the same sky as everyone else. No debris was ever found. No signal. The Pacific kept them completely.

The Miss Doran was gone too - Pedlar, Knope, and Mildred Doran, the schoolteacher the newspapers had spent a week making famous, lost somewhere over open water.

William Erwin in the Dallas Spirit had turned back partway out due to a navigation instrument failure. He landed at Oakland, made the repair, refueled, and went back out - not to race, but to search for the missing aircraft. Erwin and Eichwaldt flew into the search area and transmitted a radio message reporting they were lost and turning around. Then the radio went silent. The Dallas Spirit joined the wreckage the Pacific was keeping.

The U.S. Navy launched one of the largest search operations it had ever conducted in the Pacific at that time. Ships and flying boats covered hundreds of thousands of square miles. They found nothing - not a life raft, not a wing panel, not a fragment of anything that had been an airplane full of people.

Ten people died, counting the pre-race crashes on dry land. It was the worst week American aviation had experienced to that point.

The Reckoning

The press that had spent the summer building these pilots into heroes turned on the enterprise with equivalent energy. They called the race reckless. They called James Dole’s prize irresponsible. Editorial writers who had never sat in a cockpit explained in detail what had gone wrong and why it should never have been permitted.

Some of that criticism was accurate. The derby had been organized in a hurry, in the grip of Lindbergh fever, by people who wanted a piece of history without fully accounting for what history costs. Some of those aircraft had no business attempting an oceanic crossing. Some navigation setups were inadequate by any reasonable standard. Mildred Doran was placed over the Pacific in a plane she hadn’t chosen, on a mission she hadn’t planned, for reasons that had more to do with newspaper photographers than aviation safety.

What the Derby Proved

The criticism is true. So is this: Art Goebel and Bill Davis crossed the Pacific Ocean in a fabric-covered, wood-framed, single-engine monoplane powered by a Wright Whirlwind radial engine, navigating by the stars, and arrived in Hawaii after twenty-six hours over open water. Martin Jensen did the same thing two hours behind them.

Whatever the race cost, those two crossings proved something permanent. The Pacific could be done. The 2,400-mile crossing that took a ship four and a half days could be made in twenty-six hours. The distance separating Hawaii from the mainland was not fixed. Aviation could move it.

Pan American Airways began scheduled flying boat service across the Pacific in 1936 - less than a decade after the Dole Air Derby. The China Clippers flew from San Francisco to Manila, stopping at Honolulu, Midway, and Wake Island, opening a route that reshaped commerce and eventually the conduct of war across the entire Pacific basin.

The pilots who died in August 1927 were part of the price the aviation world paid for understanding what the Pacific crossing actually required: better navigation equipment, better weather forecasting, better aircraft. The knowledge of what goes wrong when none of those things are adequate.

The Woolaroc Today

The Woolaroc survives. It’s on display at the Woolaroc Museum in Bartlesville, Oklahoma, on the land where Frank Phillips built the ranch that gave the airplane its name. It’s a modest-looking machine for an aircraft that crossed the Pacific - fabric over wood and steel, a nine-cylinder radial on the nose, not much larger than a modern Bonanza. Art Goebel flew it 2,400 miles over open ocean in 1927.

The next time you’re frustrated with a moving map three seconds behind, consider Bill Davis in the back of that Woolaroc at two in the morning over the Pacific with a sextant, a pencil, a chronometer, and no margin for error.

Key Takeaways

The Dole Air Derby was announced in June 1927, three months after Lindbergh’s transatlantic flight, offering $25,000 for the first nonstop Oakland-to-Honolulu crossing
Eight planes were certified to start on August 16, 1927; only two finished - Art Goebel’s Woolaroc (26 hours, 17 minutes) and Martin Jensen’s Aloha (28 hours, 16 minutes)
Ten people died in the derby and its associated crashes, including the entire crews of the Golden Eagle, Miss Doran, and Dallas Spirit
The U.S. Navy conducted one of its largest Pacific search operations to that date and recovered no wreckage from any of the lost aircraft
The two successful crossings directly enabled Pan Am’s China Clipper service, which launched in 1936 and opened trans-Pacific commercial aviation
The Woolaroc, the winning aircraft, is preserved at the Woolaroc Museum in Bartlesville, Oklahoma