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"It's a wonderful day in Maine - in fact, nice enough for a parachute jump," said the 41st US president, who first jumped from an aircraft almost 70 years ago when he was shot down over the Pacific Ocean during World War 2.
Live video showed Bush soaring over a wooded area of coastal Maine, where he has long maintained a home. After landing, a support team returned him to the wheelchair Bush uses to get around.
Bush, the father of 43rd US president George W. Bush, has been celebrating birthdays with occasional skydives for years and marked his 75th and 80th birthdays with jumps.
In 2009, when he jumped to mark his 85th birthday, his son then-President Bush said: "I think he's a nut to jump."
Skies in Maine were heavily overcast with little wind on Thursday.