Toward the end of Kobe Bryant's career, Rob Pelinka decided he had to save Bryant from himself, and, well, save himself from Bryant.
So he pulled out a copy of the NBA's collective bargaining agreement and scoured the uniform player contract for language that would keep Bryant from jumping out of an airplane with a parachute, and forcing his agent to do it too.
So Bryant got wiser the next time. Shortly after his retirement, the two set out on a helicopter ride and Bryant didn't tell Pelinka of his daredevil plan. Bryant and the pilot looked at each other and Bryant nodded subtly.