John is a Stanford and whatever other faults Stanfurd has, they don't let in dummies, even if they are great athletes. If John had considered it for two minutes he'd have figured it out on his own. So could many others, in addition to those who know already.
As said before, it is Brad who pays Will's credit card bills.
So you acknowledge that Will is immature and doing things purposefully to goad Brad, primarily to interfere in Brad's life?
Most of the money isn't his and it isn't his place to offer John a room in a family apartment, no matter how noble. Remember how pissed Will gets when others do things like that.
Will didn't buy the house in Hawaii, Brad did with family money once he decided it was a good investment.
And he is doing things to provoke Brad.