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If you are wanting to build the "story" into your universe...I would treat it like he signed the extension with Ewok Village. You do see that kind of thing. A guy gets traded in his walk year and part of that deal is negotiating an extension with the new team.
As far as OOTP's AI, it has never been programmed to have loyalty to a recently signed contract. Basically, the AI is going to constantly evaluate each potential move considering everything before it as a "sunk" action. This is good and bad. It should allow the team to always be able to take advantage of what it believes to be a good move, but you will get some sets of transactions that will not make sense from a "real life" perspective.
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