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This is probably a stupid question, but did you look in the profile to see if he's already employed? If he's working for someone else, even in the minors, you can't offer him a contract. You COULD shortlist him, and have your Messages set to send you a message whenever someone on your shortlist becomes unemployed.
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Continuing a campaign to promote adding a 'mass select' option to Out of the Park 10. *sigh*
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