I think Jay Cutler can win a Superbowl under two conditions.
1. If the entire team around him is very solid. If we have a great defense, they can cancel out any mistakes we know Jay will eventually make. He's got a good offense in place for him, but the defense is horrendous and the ST was pretty terrible this past season as well. Given the contract he just signed [assuming the yearly amount is pretty high], the Bears won't be able to give him a GREAT defense and special teams unless they strike gold in the draft.
2. He has this offense in place and the defense and ST is good enough for elite QB's like Manning, Brady, Rodgers, etc. to win a Superbowl. But, Cutler would have to string together 3-4 AMAZING games to pull in off. Like Joe Flacco last season. Flacco in the post-season threw for 11 TD's, 0 INT's and had a QB rating of 117.2. Could Cutler do the same? Idk about that, tbh.