Well a couple things: first both inflation and then QB pay hyper inflation have changed the game. Generational wealth on your first big contract was not really possible at Brady's first big contract, which, secondly, by the way happened after he had a Super Bowl. Third, Brady never angered the fans of NE the way DJ did the fans in NY.
Either way, DJ was going to end up fabulously rich.....but with a team friendly deal, he would not be hated in NY City like he is now in many quarters, he would therefore have more endorsement money for sure, and I would think life would be happier. At some point the short term maxing out of the money is not really necessarily the greatest choice.
I want DJ to have the best career possible. I don't think the way he handled his contract is going to facilitate that. I think it will cost him, yes, MONEY and fans in the long run. I think this maximize every dollar today mindset is often not the best long term result. At what point Brady learned it, he learned it.....there's no law that sez other QBs have to wait to learn it. We are all allowed to learn from Brady. I wish DJ had.