I assume there have to be some. I doubt you could trade a draft pick conditional on the Yankees winning the World Series for example. What if at the deadline the Washington Capitals wanted to acquire Daniel Alfredsson? If he retires after the season the Capitals would be stuck with his cap hit for the season after, something that would act as a deal breaker. What if they came up with a workaround with conditional draft picks? To Ottawa: Washington's 1st pick Prospect To Washington: Daniel Alfredsson Conditional 1st pick The condition of the pick would be : If Daniel Alfredsson is not traded back to Ottawa for a 7th pick at the conclusion of the playoffs, then the pick is transferred to Washington. This would provide Washington insurance against Alfredsson retiring and sticking them with the cap hit. Would that work? This might set some sort of precedent though, redefining the concept of a 'rental' in the NHL.