1. Guaranteed money for NFL contracts is critical. And yes, he practically doubled his guaranteed money. I don't understand the confusion.
2. If he is still playing at a high level he will be able to command top dollar. The Pats wouldn't want to see him spend his days on a beach with Giselle so they would pay him what he's due. If he's not playing at a high level then they are still on the hook for all the guaranteed money and less cap room.
1. Because he turned his previous base salary/bonuses into signing bonus. That's not doubling it. The Pats weren't going to cut Brady. The new contract in essence turned his old contract into a signing bonus making it guaranteed and lowing his base amount while spreading his cap figure to 2017.
2. This is obvious. But the point is he already took a team friendly contract that will take him into age 40. So they'll keep paying him but Brady obviously doesn't want to be the huge salary cap burden at the expense of his team.