I think you approach him if the following are both true:
- You have a deal that you are VERY interested in doing
- He has expressed that he is at least open to waiving, including for certain teams.
If on the other hands
- You don't have a deal that is good enough
- Or the player has been clear, in any communications, he has no interest in waiving
Then I don't see the point in bringing it up with him.
In a case like with Kuzy it's very different
- The player was not playing regularly
- He is at the end of his contract
Therefore the team doesn't have to be as worried about the long-term implications of asking him to waive, and the player is probably very open to a change to get a better opportunity.
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