Originally Posted by
medod
I think probably because to him it was a flash big black helicopter with a smart VIP interior. I doubt he knew much about helicopters themselves; what models are available, avionics etc.
Might be a recommendation by a/his pilot/friends/business partner, whatever. You never know how much personal interest people with a lot of money and a lot of other concerns will take in things they consider tools and which they don't drive personally.
I have not been in business aviation, but colleagues who took that route out of necessity reported that there are charter clients who specifically ask for "a safe pilot" and others who don't because they don't care. I'd suppose if I were a millionaire hiring a pilot I'd ask him to not fly if he has any doubts about safety as I'd value my ass even more than his, but apparently this attitude is not universal. This is in no means directed at Kobe Bryant whom I don't know (not interested in sports) but a more general observation. Maybe continued success breeds a feeling of invincibility.