The Dole Air Race, the Pineapple Derby of 1927, and the Pacific Ocean That Swallowed Six Planes in a Single Afternoon

On August 16, 1927 - just 89 days after Lindbergh crossed the Atlantic - eight aircraft departed Oakland Municipal Airport bound for Honolulu. Only two arrived. The Dole Air Race, nicknamed the Pineapple Derby, remains one of the deadliest aviation competitions in American history, and its central lesson about flight preparation has not aged a day.

What Was the Dole Air Race?

In the summer of 1927, aviation fever had seized the country. James Dole, the Hawaii pineapple magnate, posted a $25,000 first-place prize (over five years of average American wages at the time) for the first pilot to fly nonstop from Oakland to Honolulu. Second place paid $10,000.

The course covered 2,400 miles of open Pacific Ocean with no intermediate islands, no emergency fields, no radar, and no meaningful navigation aids. The only question the prize asked was whether someone could do it. It did not ask whether anyone was ready.

Who Entered the Race - and What Happened Before It Even Started?

Twelve aircraft originally entered. Two crashed during pre-race qualification runs - one overran the runway on takeoff, another shed a landing gear on a practice flight. Both crews walked away. The organizers noted the accidents and continued.

Eight planes lined up on race day. They fell into two distinct categories, though nobody announced it that way at the time.

The prepared crews:

• Woolaroc - a Travel Air monoplane funded by Frank Phillips of Phillips Petroleum, named for his Oklahoma ranch. Pilot Arthur Goebel was an experienced barnstormer and exhibition flyer. Navigator William Davis was a U.S. Navy officer with real Pacific ocean routing experience. They carried a drift indicator, had worked through the celestial navigation problem thoroughly, and ran their fuel numbers multiple times.

• Aloha - Pilot Martin Jensen had logged extensive flying in the Pacific region and understood what featureless open ocean looked like from altitude. Navigator Paul Schluter was an experienced partner. They had planned not just for the flight going right, but for specific ways it could go wrong.

The under-prepared crews:

• Miss Doran - named for Mildred Doran, a 22-year-old schoolteacher from Flint, Michigan, flying as a passenger purely for the adventure. Pilot John “Auggy” Pedlar was a capable flier. Navigator Vilas Knope rounded out the crew. Doran had barely been in an airplane before the race.

• Golden Eagle - pilot Gordon Scott and his navigator.

• Oklahoma, El Encanto, and Dallas Spirit - pilot William Erwin with navigator Alvin Eichwaldt aboard the Dallas Spirit. Several of these crews had navigators with, at best, uneven ocean navigation experience. They had compasses, charts, and the unshakeable confidence of 1927 that the age of flight meant everything was possible.

How Did the Race Unfold?

The race started at 12:32 p.m. The planes departed one by one, heavy with fuel, climbing out over San Francisco Bay and turning west.

The Pabco Pacific Flyer got roughly two miles offshore before the engine quit. Pilot Goddard turned back. That was the fortunate outcome.

The Dallas Spirit had mechanical trouble before the start, returned to Oakland for repairs, and then Erwin did something that defines a certain kind of pilot: he took off again, hours behind the rest of the field, alone, with the prize still technically on the table.

The Woolaroc flew through the night. Goebel navigated by dead reckoning, using stars when the sky was clear and the drift indicator when it was not. He later described the hardest part as the darkness - no horizon, no visual reference, just the sound of the Wright Whirlwind engine and an instrument panel dimly lit by whatever 1927 could offer, and somewhere ahead, an island he had to find.

Twenty-six hours and seventeen minutes after leaving Oakland, the Woolaroc appeared over Diamond Head. Goebel landed at Wheeler Field to a crowd that had been waiting through the night. He was handed a check for $25,000.

The Aloha arrived two hours later. Jensen and Schluter collected $10,000 for second place.

Two planes. Out of eight starters.

What Happened to the Missing Aircraft?

The Golden Eagle - Gordon Scott and his navigator - never arrived. No wreckage. No distress calls. No trace.

The Oklahoma vanished over the same ocean. Same result.

The Miss Doran sent a radio transmission roughly four hours out of Oakland - routine position report, nothing alarming. Then silence. Mildred Doran, Auggy Pedlar, and Vilas Knope were never found.

The search efforts compounded the tragedy. The El Encanto, which had turned back early with mechanical problems, went back out to join the search and did not return. A Navy Fokker trimotor assigned to the search caught fire in the air and went down.

The Dallas Spirit began transmitting increasingly distressed radio messages as Erwin’s navigation deteriorated. He radioed, according to newspaper accounts of the time, that he was lost and asked which direction was land. Shore stations answered him. Whether he heard the response is not known. The Dallas Spirit went silent. William Erwin was never found.

Final toll: ten people dead. For a race. For a prize. For the aviation fever of 1927.

Why Did So Many Planes Go Down?

Congress held hearings. The Department of Commerce - which then regulated civil aviation - investigated. Their findings were direct.

Two thousand four hundred miles of featureless ocean is not a cross-country flight. On a cross-country route, a pilot picks up position constantly from rivers, railroads, cities, and landmarks. Over the Pacific in 1927, the crew had a compass, a watch, dead reckoning calculations, and whatever celestial navigation skill they had or had not developed before the start.

A ten-degree course error held for 300 miles means missing the island entirely. Hawaii is not small, but it is surrounded by an exceptionally large ocean.

Several Dole entrants carried navigators who were, in the blunt assessment that emerged afterward, learning Pacific navigation while crossing the Pacific. One navigator reportedly had essentially no practical ocean navigation experience before the race. They were relying on the compass being close enough and the flight time calculations being close enough, and hoping that close enough would be sufficient.

Aviation does not negotiate with “close enough” over 2,400 miles of open water.

What Did the Survivors Say About Why They Made It?

Martin Jensen’s post-race account is the lasting document from this event.

He said that he and Schluter had sat down before the race and planned specifically for the things they did not want to happen - not the things they expected, but the failures: engine roughness, unexpected headwinds, a compass that drifted, navigation errors that accumulated. They identified each failure mode and decided in advance what to do about it.

On the flight, several of those failures actually occurred. And because they had already decided on their response, they executed the response and kept flying.

Jensen’s conclusion: the difference between the pilots who made it and the pilots who did not was that the survivors had planned for failure. The others had planned for success.

Where Is the Woolaroc Today?

The original Woolaroc aircraft is preserved at the Woolaroc Museum and Wildlife Preserve in Bartlesville, Oklahoma - Frank Phillips’ ranch that gave the plane its name. The aircraft is on public display.

The cockpit is small. The instruments are minimal by any modern standard. The fuel tanks dominate the airframe. It is the actual airplane that flew 2,400 miles over open Pacific in the dark in 1927.

Arthur Goebel went on to a long and full life. Martin Jensen built a distinguished aviation career. The others are memorialized on plaques in aviation museums - plaques that read lost at sea, August 1927. Mildred Doran has a street named after her in Flint, Michigan. She would have turned 23 later that year.

Key Takeaways

• The 1927 Dole Air Race sent eight planes from Oakland to Honolulu; only two arrived, killing ten people in total
• The two crews that survived - Woolaroc and Aloha - shared one characteristic: they had planned specifically for navigation failures and equipment problems before departure
• Over-water navigation in 1927 offered no checkpoints and no margin for course error; a 10-degree drift held long enough meant missing the target island entirely
• The post-race federal investigation identified inadequate navigation preparation as the primary cause of the losses
• Martin Jensen’s lesson remains the operative one: plan for what goes wrong, not just what goes right - this applies to every flight, regardless of era or equipment