The Cleveland Cavaliers have lost three of their last six games but they still comfortably have the best record in the Eastern Conference. There are some that think the Miami Heat can challenge the Cavaliers to win the East but that is contingent upon Chris Bosh getting back on the court. For the most part many people still expect Cleveland in the finals.
When and if the Cavs get to the finals, nobody expects them to win whether they face the Warriors or the Spurs. That is likely what is running through LeBron James' mind as he is set to enter free agency yet again. The Cavaliers are a very good team but their peak may just be making it to the finals and then losing to a better Western Conference foe, which is unacceptable to the King.
James structures his contracts so that he could become a free agent every offseason as a way of maximizing the money he makes. He also does this so that his team knows that if he is not happy with the roster they have surrounded him with he could leave. James' recent actions on social media, in interviews and on the court have suggested he may be considering leaving Cleveland again but the Cavs don't think that will happen.
The Cavaliers organization is reportedly confident James won't leave his hometown team again but they do realize it is at least a possibility, especially if they don't win the championship this season. Many people close to this situation feel the same way about LeBron potentially leaving, they don't see it happening but a bad showing in the playoffs can definitely alter his thought process.
LeBron is now 31 years old and realizes that his window to rack up championships is beginning to close. Even if he stays, it is very possible that LeBron will demand that the Cavaliers reconstruct their roster and they are kind of at his mercy at this point. If they say no, he will likely leave and go somewhere that gives him a better shot of winning.
The Cavaliers right now are operating under the assumption that James isn't going anywhere anytime soon, and they should because that is still very much the likelihood. Cleveland should definitely also have a plan B though, just in case the playoffs go worse than expected and it frustrates LeBron to the point of leaving. If LeBron left Cleveland this offseason, it would cripple it significantly.
But look at the Heat - LeBron left them two summers ago and they have recovered very quickly, so it is a possibility as long as there is a plan in place. Confidence from the organization is fine in this scenario but there is a fine line between being confident and being naive. LeBron has left Cleveland to chase championships before so he is not above doing it again.