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OK, found the problem. When you're converting a player from D to F or vice-versa, his starting template is remaining the same, and part of the contract demand system is relying on that template to determine what roles are acceptable to him. The only way to correct it is to go into commissioner mode and switch the template manually on his edit screen (it's under personal details) - e.g. for Pruden, to one of the "Winger," options. (In his case, since negotiations are broken off already, it won't help immediately, since he remains in that state for a while, but if you were to switch his rights to a different team he'd be signable by them immediately.)
Since you're in challenge mode, you'd need to cheat a bit to enable commissioner mode editing: to do that, make a backup copy of your game_settings.dat file, then start a new game with challenge mode off, turn commissioner mode on it it, and then exit and save it. Copy game_settings.dat from it to your regular save, then you'll be able to load that one and edit players. Do that, then exit and delete your game_settings.dat and replace it with the backup you made originally and you'll be back in challenge mode when you reload.
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