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Whenever a player holds out under contract, most fans side with management. If Brady held out for the first three games and the Pats got creamed, most fans would be pissed at Brady. A lot of them would turn on the guy. Look at what happened to Asante Samuel (who wasn't even under contract) and Deion Branch. Personally, I would be peissed at Brady if he held out while under contract, but I wouldn't turn on him.
As for Brady's brand, I do have a marketing background and it looks pretty obvious. Besides, Brady isn't great on TV as we saw on his SNL appearance or his Snickers commerical (the commerical was funny, but his acting left a lot to be desired) or Visa commericial (where the o-line outshined him). Aat least he isn't as good as Manning. As much as I hate Manning, I can recognize he is a natural TV pitchman and can sell almost anything (in fact, he might be the best athlete pitchman in a long while). Brady comes off a bit stiff on TV. That's why Brady uses his model looks to sell more stylish products while Manning uses his personality which comes out more naturally on TV.
I love Brady and all that, but TV commericals are not his strong point and that is why he isn't on them like Manning. Manning is great at it and that is why major companies are lining up to get him for commericials. I'd rather have Brady on the football field, but I would rather have Manning pitch my product on TV.
You might be right about how Brady pursues endorsements, despite the consequences of much smaller paydays. My own view has always been that Brady has a long term plan to re-brand himself after football and that he has foregone more obvious vehicles for that reason, but you might be right.