Essentially the whole issue is CBA rule 13.12j, which states that NHL teams cannot loan players to other leagues after the NHL trade deadline unless
a) they were already recalled
b) qualify for a conditioning stint
c) an injury during the trade deadline prevented them from being loaned (with some other conditions)
So if a player is signed to an NHL deal after the trade deadline, the NHL team cannot loan them to an AHL team.
However to get past this rule, NHL teams can sign a player to an NHL contract that begins next season, but then have the player sign a try out with an AHL team. This allows teams to bypass 13.12j as the NHL team is not loaning a player to the AHL team after the trade deadline.
So in summary it depends on whether the player was signed before or after the trade deadline and when the contract starts nothing to do with draft rights/free agents.
Why do some players get an NHL contract this year and some get it starting next year? It is completely up to the teams and players to negotiate.
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