Same thing happened to me with Central Defender while I was at Liverpool.
I found a better younger defender so I decided to get rid of the one I had. I could barely get teams to pay 8 million for him. I decided to exchange him with the player I wanted + I had to give them 4.5 mil. They sold him in a week or so later to Chelsea for 20.
ac milan's kepper could have just left in the first week and the second wanted chelsea's but chelsea wanted a ridiculas amount for him. carlos vela wanted a bigger tema in my game so i enquired, arsenal wanted 45 mil (aye right!) two weeks later he hands in trasnfer request and i get him for 19 mil!
alot of transfers depend on the smallest of things. the value system in fm i think it totaly screwed in 09