Has a team ever not kept a player because of a conditional pick? I can see a player attached to a conditional pick not liking it, but in the big picture I feel it is a huge benefit to players, to help them get traded to a place they are more needed.
Although maybe they would prefer the sign and trade model, where all sides hash out a deal and the player ends up where they want to be for sure. But that's not so realistic imo. In the end, the conditional pick route is the smoothest
There was another angle that it was unfair to a player traded with a penalty pick clause if traded again. E.g. Erik Karlsson from Ottawa to San Jose included a clause that San Jose had to give up a 1st pick if Karlsson ended up on an Eastern Conference team before the end of the season.
Ottawa wanted Karlsson out of the East, but it was really unfair to him personally to include that clause. Say things didn’t work out in San Jose and Karlsson demanded to be traded then San Jose is hamstringed to only moving him to less then half the NHL teams.
I think the change to remove all these conditional picks was healthy for the players. Once a team trades a player they should forfeit all influence over where a player is next traded to or what team signs him to his next contract (including the team they traded the player to).
These changes will balance out in trade returns going forward as we’re already seeing,