I think you are borrowing trouble. If he is performing well in the first two years, will you be actively worried about the back end of his contract? I like to live in the moment when it come to sports. That is just me. I am not criticizing you for worrying about the future. Different strokes. I save my worries for my real life. Baseball is fun for me, and if the idiot owners want to throw around their money like it is Monopoly money, that is their business and their worries. The financial aspect of sports is so far out of hand that average people just can't relate to it. I am not worried about the Red Sox running out of money or going out of business. They will find a way to be very profitable, and they have a huge advantages and resources compared to other franchises, so I am not worried about them crippling the team with bad contracts. And really, how much worse could they do than 3 last place finishes.