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The former commander-in-chief took the plunge just after 11 a.m., plummeting through the air until a red, white, and blue striped parachute bloomed above him, ABC News said.
He floated for several minutes over the scenic town before touching down in front of a cheering crowd of friends and family – including his son, former president George W. Bush, and his great-granddaughter, baby Mila Hager.
As he and his companion tumbled onto the lawn face-first, aides ran over to untangle Bush from his harness and assist him into his wheelchair.
His wife, former first lady Barbara Bush, congratulated her husband with a few big kisses. Bush flashed a thumbs up sign.
Bush was joined by Mike Elliott, a former member of the U.S. Army Parachute Team and the president of All Veterans Group, according to a statement from Bush's office.
This isn’t the president’s first skydive: He celebrated his 75th, 80th and 85th birthdays the same way.
But according to the statement, “President Bush's first parachute jump took place when he was shot down over the Pacific island of Chi Chi Jima on September 2, 1944.”