Re-acquiring Retained Player
Can Team A trade a player in the offseason to Team B and re-acquire said player at the following trade deadline with money retained by Team B? An example of the situation I am thinking about is can Calgary acquire Monahan at the upcoming deadline with money retained, even after having traded him in the offseason?
Answer
No, a team cannot be involved in a retained transaction for a player that was on their roster within the last year if the player is still under the same contract. So in your example, if Calgary cannot re-acquire Monahan until June 30 in a retained salary transaction. They could re-acquire him next Fall in a retained transaction because he's a free agent this summer and he would be on a new contract. Similarly, Montreal cannot trade Monahan and retain salary and then re-acquire him back within a year (or until he's on a new contract).
