Brandon Phillips is a 32-year old second basemen with the Cincinnati Reds. This is all well and good; however, he is scheduled to make 50 million the next 4 years which is the remainder of his contract. Even though he hit very well for the season, he did almost nothing the last two months. Herein lies the rub. Would the Reds be better off trading him now when his defensive skills are recognized as the best in baseball? The Reds are worried that what they saw in the last two months might be a trend following a serious arm injury caused by a thrown pitch. Also, if they free up this 50 million, they can go after Choo with a larger contract, try to sign Bailey to a long-term contract, and pursue a free agent or two. The danger in all of this is that you know what you have in Phillips and you don’t know if the players in your system can fill this void. Phillips will be 36 when his contract runs out, and there are very few teams willing to trade for 36-year old ball players. Most of them go as free agents and you are left with nothing. What would you do?