I think it depends on the player.
Usually I'd be inclined to sell him straight away when that happens, or at least the year before his contract runs out but atm I'm managing Atletico Madrid, and since I started Pablo has wanted a new challenge but never requested a transfer, after the 2nd season I dropped him entirely and transfer listed him at the end of the season, no bids came in and by the start of the new season he was happy again and signed a new contract.
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