You can ask a what if on all teams....but I don't hear them about your questions you brought up...no questions on what if with Brady, Brees, or anyone else really. The reason is IMO because it's not really a what if question...it's more of a what I would like to see happen statement presented in a what if type question.
If it's not that then the whole premise of the what if it is just stupid.....as all have said you can what if till the cows come home...IMO it's simply a wishful hope/thought presented in a question style....they do it in politics all the time...it's just flowed into sports......a sad natural progression I guess.
