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What's more, he'd need to do a third major image overhaul to be marketable after football. Where's his agent to explain that?
And just to digress even more, Adam Vinatieri essentially made the same mistake. He got a few dollars more in Indianapolis, but failed to recognize the decades of endorsements he could mine in the Boston market after football. Now, he gets none of that. In Indy, with Peyton Manning, he'll get none of that.
Where are these agents to explain these things?
I think this is one of those places where players' and agents' interests diverge, and it really hurts the players. IIRC player agents don't routinely handle endorsement contracts -- a separate marketing manager does that. Assuming that's the case, then the agent doesn't care one bit about the player's outside and post-retirement earnings potential.