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I dont think its because he was born rich it was because he was so good in the beggining he didnt NEED to work hard,and then when it came time where he had to work hard,he didnt want to.Penn certainly wasn't soft but he also wasn't willing to put in the work to be his best and that is likely at least partially because he was born rich.
Sure it helped that he was rich,but really it came down to it being alot easier when he was younger and way ahead of the game