Again, this whole concept assumes you could get him to sign an extension. As mentioned above, all players and agents say they are going go to test the market, however there are teams that are able to lock up those players before they make it to the market (See: Felix, Verlander, Kershaw (soon), Cain, etc etc etc) If you offer a good deal, the player will listen and often times take it. It takes two to tango, the Reds have been said to be looking to shed payroll, so while Bailey is "unlikely to sign an extension with them" they are probably not making him a legit offer to sign him and are choosing to invest in other areas. It reminds me of the Johan Santana situation, Johan was "unlikely to sign with the Twins" not because he was against signing before reaching free agency, but because the twins were obviously putting their assets in other places (morneau, Mauer) and weren't offering him anything close to a fair market deal. He got traded to the Mets and instantly signed a large extensions. Same thing with the Reds, they are choosing to invest in other areas. That doesn't mean another team that trades for him can't give him the fair market value (and safety) that a extension would bring prior to the season. Keep in mind, as a pitcher there is always risk of elbow/arm problems, so if the Twins offered him 6/100, he would have to think long and hard about accepting IMO.