9. Pittsburgh Steelers
If I was Jay Cutler, I would come to the Pittsburgh Steelers. There isn’t a better spot for him in my eyes. The Steelers are a winning organization with an obscene amount of weapons on offense. They have a future hall of fame quarterback in Ben Roethlisberger, but Big Ben has proven that he is no longer durable. He’s only had two seasons where he has played 16 games since 2009. If Cutler comes to Pittsburgh, he’s going to be a part of an organization that is going to be in contention for a Super Bowl and he is almost certainly going to start a few games.
Whether Cutler is willing to start the season on the bench and wait for an opportunity may not be something he’s willing to do. But there is no better position for Cutler than Pittsburgh. Cutler is almost certainly going to look for a team where he will be the starter this offseason. He probably won’t have the mindset of taking a second string spot for another couple of years, but if he was willing to put his ego in the backseat, Pittsburgh could provide him a tremendous opportunity.