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You could say the same thing about Dan Fouts, Dan Marino, Jim Kelly and others.... Takes the perfect storm to be a "winner" in the NFL few QB's do it on their own. Then you have QB's like Dilfer who blow and have a SB ring.
Will be interesting to see where he is stats wise and win/loss wise in about 10 years.
IMO, he's not going to be at that level. I'd still call those guys "winners". They all had lots of playoff appearances, and playoff wins, and no one doubts that the Chargers, Dolphins and Bills would've been far less without them.
What has Cutler done? He has yet to get a team into the playoffs or win a playoff game. Let him prove he can lead a team into at least that level of success and I might start to change my mind about him. I admit, I thought he was one of the most overhyped players of all time when he was in the draft, so I've never really liked him.