MULBERRY, Fla. (AP) — A plane became entangled in the strings of a skydiver's parachute, sending both crashing into the ground near Tampa, Fla., with both the pilot and jumper hospitalized with minor injuries.
Polk County Sheriff's Office spokeswoman Carrie Eleazer says 87-year-old pilot Shannon Trembley was doing takeoff and landing maneuvers Saturday in his Cessna at the South Lakeland Airport in Mulberry.
On his third landing pass, the wing of his plane became entangled in the strings of 49-year-old Gainesville skydiver John Frost's parachute about 75 feet above the ground.
Frost was flung to the ground, and Trembley's plan nose-dived to the surface as well.
Eleazer says neither sustained serious injury, but went to the hospital. Frost was treated and released. Trembley was held for observation.
The National Transportation Safety Board and FAA are investigating.
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Skydiver, pilot treated after midair accident

This was one sport I never tried, mostly because a co-worker, a girl came into work one day and the love of her life had just died skydiving. After that, any desire to sky dive for me was gone. However, my step-son has sky dived many times and bungy jumped as well (which is another sport I decided not to try).

Also, there is a video of when the plane taking off catches the chute of the skydiver and slings them both to the ground at the above word button. 

However, I have piloted many planes, gliders, and hang gliders over the years and had a lot of fun doing that.