Career Mode: Player signed new contract he asked for, still requested transfer

A player was requesting a new contract to get better wages. I signed him to a better contract. He somehow still requested a transfer despite having high morale and being happy in every morale category, including his contract. I've been ignoring transfer offers for him but the board even sent me a message saying I haven't done anything to resolve the issue even though I literally gave him a new contract. 

So I am going to be forced to sell my best player, and this is after I was forced to lose my other top player because apparently anyone with a release clause will not sign a new deal with you if they are approached by another club. I don't understand the point of a morale system if people who are happy still request transfers or still refuse to negotiate new deals with you. The contract system this year is absolutely maddening.