That's the argument for trading Cutler now and moving on, I think. If you view the new coach as the next long term direction, and Cutler has his own shelf life, why not start over entirely ASAP? The answer to your question is because quarterbacks don't grow on trees. You could trade him tomorrow and never come close to competent QB play for 10 years, enough to cycle through 2-3 more administrations. Cutler gives you the best chance to be competitive next year and going forward until you find (probably draft and develop) his replacement.