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Originally Posted by blackrussian
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Yes, but the third contract was a normal offseason free agency contract, which the OP's player inevitably would have signed after 11-22. The progression is going Mexican League free agent->Major League stretch rental->Major League free agent.
Perhaps the real thing that needs to be tweaked here is eligibility. The game could probably benefit from a posting system a la Japan in this regard so players can't be signed for the last month of the season as seems to be the case.