Police in Titusville, a town approximately 40 miles east of Orlando, said the two adult men had jumped together from a plane that had taken off from nearby Dunn Airport.
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Eyewitness video showed the two men in a free fall, circling one another as they plummeted toward the ground. Police said the two men hit a tree and landed in the front yard of a home on Tennessee Street around 10:30 a.m. local time.
Both men were taken to the hospital via helicopter in critical condition. Their identities were not released.
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Nobody on the ground was injured.