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It's not only about fun, ok their job is skiing, but money is still important to live.
After his career, he won't earn as much as now, so he cares about money as you and me. Bobby is this kind of skier, working hard to have the biggest tricks in order to win contests, and it works. Pro-skier doesn't mean that you're food is free! It's also what makes them live that's why contests are important.
On the other hand, judging is style is totally subjective. To me his part in The way I See It is just so sick. But that's true he is not the best at rails, so he does crazy tricks on kickers, does it mean he brings something negative for the sport? I would never go that far even if I know what you mean, he still has a lot of style, and to me style doesn't mean only smooth rails or butters or whatever everyone is trying to do nowadays, his Dubs 10 look so smooth and easy that it's so stylish!