Goalie Ken Dryden graduated from Cornell University before playing in the NHL, then earned a law degree from McGill University in the middle of an eight-season NHL career that included six Stanley Cup championships and multiple individual awards.
"I saw Ken Dryden doing that, and it just kind of motivated me to not only play hard in hockey but do well in school," O'Shaughnessy said.
O'Shaughnessy played at Marian High School. The son of a private pilot, he also wanted to fly. The Air Force Academy offered the opportunity to chase dual dreams. Halfway through his freshman year at Air Force, he was called up to the varsity. Teammate Joe Doyle, now an Air Force associate coach, said he was "quiet in the room" and "really cerebral."
"He was one of us, but he was also way sharper than us," said Mark Manney, a teammate who would go on to fly Air Force One. "You could tell that his future wasn't in hockey. It was in doing great things with the military or whatever he pursued after graduation. It's a whole different level of smart."
O'Shaughnessy graduated in 1986 and became a command pilot with more than 3,000 hours in the F-16 Fighting Falcon, including 168 combat hours.
He said balancing the demands of a Division I athlete and those of a cadet taught him time management and work ethic. Hockey taught him teamwork -- putting on a uniform, counting on your teammates, making sure they can count on you, serving something greater than yourself.
He drew a line from the crease to the cockpit. You must have vision, think fast, anticipate. You never fly alone, relying on your wingman. You come up with a game plan, execute it and review your performance, constantly striving for improvement.
"Playing hockey and being a fighter pilot are so similar," he said. "The attributes that make you good at one make you good at the other. … For me, it was a real easy transition, to come out of the academy and then go and be a fighter pilot."