Cowboys have holes all over though, starting with QB, which is enough of a concern that you shouldnt be talking superbowls.
As for Grossman, he shows flashes, but so did Orton. He is far from the worst starter in the league, hell he is the 2nd best starter in the NFC North(meaningless I know) but he isnt a good QB and really hasnt show much to say he will be. Throws a pretty deep ball, but his intermediate and short stuff is all over the place, his checkdowns are almost random and it only takes a couple of bad passes or plays and he just loses all confidence and one healthy season doesnt cancel out the fact he has never been healthy before. Grossman to me is a guy who should be a backup. With the way the Bears team is set up I'd rather a QB who will neither win nor lose a game than one who can win or lose it on any given day. The Superbowl is a prime example, if Grossman doesnt keep giving the ball to the Colts the Bears might have had a chance.