The former Prime Minister is on his way to adding another qualification to his impressive portfolio, passing exams to become a qualified chopper pilot.
With developer son Max as a passenger in the back and an instructor alongside, Key flew the craft from take-off to landing.
The 26-year-old Max chronicled his famous dad's first flight and posted it to Instagram this morning.
It begins with a shot of Sir John posing alongside the chopper in a hangar and captioned: "The big fella taking me for his first fly! Just passed his exams."
The pair then push the craft to the pad, Max mentioning how "all those reps in the gym" have come in handy.
As Sir John starts the engine ahead of take-off, Max makes the Sign of the Cross, a silent prayer for a safe flight. The instructor is alongside Sir John, showing him the ropes ahead of taking to the sky.
But there's a moment of alarm midair when a warning light can be seen flashing on the dashboard.
"Master caution light flashing epic," posts Max.
However, everything seems to pass without incident as the helicopter lands safely.
As soon as Max gets out of the helicopter he kneels on the ground, kissing and worshipping it with a brief post: "Update!! I lived".
Sir John can be heard laughing at his son's over-the-top reaction and exclaims: "We made it!"
Last month, Sir John and Max Key announced the launch of Stonewood Key Capital, a venture with property brothers and one-time brothel owners John and Michael Chow.
The company has a target of raising $100 million over the next 18 months to buy land for housing developments, hoping to add 500 new homes annually.
Prior to that, Max had stepped out into development in the Auckland housing market relocating and renovating homes in Mt Albert and Glen Innes.