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Both pilot and skydiver survived.
In fact, neither the pilot nor the skydiver suffered serious injuries, the Polk County Sheriff's Office said.
The pilot, 87-year-old Shannon Trembley, had been practising landings and take-offs with his private Cessna at South Lakeland Airport near Tampa.
During one of Trembley's approaches, the passenger-side wing got caught in the strings of John Frost's parachute as Frost came in for a landing.
Frost, 49, was treated at a hospital and released. He couldn't be reached for comment.
Trembley, who lives near the airport, was being kept at Lakeland Regional Medical Center for observation, the sheriff's office said.
A hospital spokeswoman told the Los Angeles Times that Trembley did not want any information about his condition shared.
His plane's front propeller broke off and the tail of the plane also suffered damage, according to pictures.
Tim Telford, a photographer who captures skydivers landing, said Frost was among nearly a dozen jumpers coming off the Skydive Tampa Bay plane at the time.
"I could hear the plane coming, and I thought I would just get a close shot of the plane and skydiver being scary-close," Telford told The Times. "I turned and just stood on the trigger."
The result was a series of dramatic photos.
Telford said the pilot in the skydiving plane had gone on the local radio frequency shared by pilots and the airport to call in the usual warning - that jumpers were in the air, so pilots in the area should exercise caution for the next several minutes.
"This is nothing I'd ever expect to see," Telford said. "Thank God everybody came out OK on this one."
The National Transportation Safety Board and FAA are investigating the crash.