The retention thing is a simple negotiating ploy. At the end of the day they would weigh the best offer retained vs. best offer no retention and decide accordingly. Far more likely they take back a contract with shorter term instead of retaining, which may generate a return at it's last TDL.
A big question is how contract insurance works in the event of a trade. I couldn't find much recent info, but it seems most teams insure their highest paid 5-7 players through a league-wide policy (Geico) and premiums are determined accordingly...but I wonder how that works with a player trade? Would the coverage/premium be transferable?
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