I think the article itself was pretty thin evidence of anything. Along with shoe contracts I am sure all the top prospects are getting dizzy with the number of things that are presented to them. Simmons has good basketball ability, nobody is saying he is a financial genius or capable of sorting all this stuff out for himself.
Simmons and Paul can't pick teams to come first or second in the lottery, so longer term considerations like who is most likely to be successful in the next few years are beyond their control, shoe contracts they can look at. If Paul was doing his job well he would be telling his client that the Celtics are on the verge of being one of the greatest basketball dynasties since...the Boston Celtics, and he could make more long term by being a winner there.