The extension removed a lot of our flexibility and options with Hughes. Without a long, solid history, you should almost always prefer a pitcher on a 2/16 deal (what he had left) over a 5/55 deal, especially a backloaded one (what we gave him with the extension). Under the pre-extension scenario, you seem to be worried about how much he will cost to retain if he continues performing well over the remaining two years, but you are ignoring the fact that he would have been an INCREDIBLY valuable trade piece under those circumstances, or fetched a valuable comp pick this winter. (Or, if we really wanted to retain him, he'd probably be worth the $75+ mil he'd command after 3 strong seasons.) Even with performance regression, he would have been a decent trade chip. With injury or a lot a performance regression, we would have had the inside track to re-sign him on a one-year bounceback deal like that of Tyson Ross. So there really was no "bad case" pre-extension, it was pure upside for the Twins. As it stands, the extension made it virtually impossible to trade him for several years. Even now, if he fulfills our hopes and returns to usefulness in 2017, he is probably not a trade asset for at least 2 years unless we eat cash. We really have to hope for 2-3 years of health and usefulness from him.