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If you're dealing with the very team that made you who you are and you just came from? yeah I do. And we're talking about a lot more than just a QB choice. This a franchise make or break move. If Cassel becomes the next Scott Mitchell than Pioli's cooked in about 5 years from now.
1.) It's his first "big" decision. He'll get a pass on it.
2.) The Chargers were able to overcome Ryan Leaf in less than 5 years.
The key in football is to get a quarterback who can get the job done. It doesn't matter how you get him. Just look at some the Super Bowl winning QBs from this decade:
Brady (6th round)
Roethlisberger (1st round, but out of top 10)
Manning (#1 overall)
Manning (#1 overall)
Johnson (9th round)
Pioli knows this. If he thinks Cassel's the real deal, the last thing he's going to worry about is the fan base whining about it.