On the morning of April 30, 1926, Wills and Bessie arrived at Paxon Field with John Betsch, the Welfare League's publicity chairman. As Bessie planned a parachute jump later in the day she wanted to check out the field for a good landing site, so she asked Wills to fly. Seated in the rear cockpit of the Jenny, Bessie left her seatbelt unfastened so she could peer over the edge of the cockpit and check the field. Wills climbed to 2,000 feet and circled for about five minutes. He then climbed to 3,500 feet and headed back to Paxon Field. Aviators who witnessed the flight said the airplane went into a tailspin at 1,000 feet.

It then flipped upside-down at 500 feet, tossing Bessie out of the cockpit. After somersaulting end over end she hit the ground crushing nearly every bone in her body and her dreams for a flight school for her people. Wills in the meantime was struggling with the airplane's controls but failed. The plane crashed after shearing off the top of a pine tree near the edge of the field. Ironically, when police and Betsch arrived, Betsch was shaking so bad from shock that he decided to light a cigarette. The spark from the match ignited the gasoline fumes immediately engulfing the airplane and Wills' body in flames. The cause of the accident was discovered immediately in the charred remains. A wrench had slid into the control gears and jammed them.