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Excellent point.
There should almost be several facets to something like this.
a) You take a hit if you do not choose to re-sign him and he goes to FA at the point of that decision.
b) You could recoup some of that if you actually do re-sign him later of course (which is doubtful).
c) You would take a greater hit if he signs within you league and/or division (which might be tough for the game to actually calculate, but would be cool).
And the second two above should scale if he waits through half a season to decide as you originally stated, regardless of the above.
Just another one of those behind-the-scenes things...
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