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I managed Boston United.
Our club legend Paul Bastock will retire after this season. Luckily, his coaching attributes are awesome ! Then I approached him in June and he also pleased to sign a 5-year coach contract with 20 p/w (6).
But, after the end of his current contract (30 June @ St.Albans). He became jobless, rather than work as my coach.

Is Bosman rule doesn't work on player who planned to retire?
 
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Well, 20p/w isn't exactly a lot. What is more if he did sign for you for 20p/w, he would be able to be poached by bigger clubs extremely easy as they would have no trouble paying the compensation ect.

AFAIK, there is no difference when it comes to signing a coach. Does he want to resign from the game completely? Have you told him he would make a good coach? Does it say in is profile that he would like to take up coaching? These things will affect his decision.
 
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Oops ?! He still have other choice even we have signed a contract ?

BTW, I solved it by loaded previous save and sign him through "Approach to buy".
 
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