I think he is sending a message to the front office that he wants them swinging for the fences this off-season. He has a couple good years left and wants to win another ring. I think that is a defensible course of action to mortgage some future picks/cap space to win while you have an elite but aging QB.

The Browns have a top of cap space every year and yet have no realistic shot at the playoffs let alone a championship. Granted, it has not worked out for the Saints, but why would you not try? One really bad year after Brees retires and your cap situation can be resolved.

 

I seriously doubt that he'll actually retire this offseason. He would have to pay the Steelers back almost 20 million in bonus money that he got with his last contract extension. IMO, the most likely case is that he plays two more seasons, and then perhaps steps away after 2018. Pittsburgh's dead money hit would be much more managable at that point as well.

 

Yeah as really think if he does win a SB. He may retire like Peyton Manning did out on top.