Cashman jumped with the U.S. Army Golden Knights in a plane from Homestead Air Reserve Base outside Miami, a fundraiser for the Wounded Warrior Project. He was hurt on his second jump Monday.
The Yankees said X-rays at Homestead Hospital revealed a broken fibula and dislocated ankle. Cashman was scheduled for surgery later in the day with Dr. Dominic Carreira at Broward Health Medical Center.
"I'm in great spirits, and it was an awesome experience," Cashman said in a statement. "The Golden Knights are first class. While I certainly didn't intend to raise awareness in exactly this fashion, I'm extremely happy that the Wounded Warrior Project is getting the well-deserved additional attention."
The 45-year-old, who has been the team's GM since February 1998, also has rappelled down a 350-foot, 22-story building in Stamford, Conn., sometimes dressed in an elf's costume the past three Decembers as part of the town's "Heights and Lights" celebration.