The Browns are George Costanza......every instinct they have has been wrong, so you should always do the opposite. They pay Osweiler a huge amount of money to not play for them. Therefore the correct move is to pay Osweiler a very small amount of money to play for you.
More seriously-the Browns are in a strange position. They have money to burn, and are tanking and stocking draft picks. They never planned on playing Osweiler, even though they took on the huge salary, but he must have shown them enough in camp to make it tough.
Overall though, I hope Elway never once faces a decision and asks "What would the Browns do?"