Lillard has been trying to force his way to Miami all offseason. Trade talks have been at a standstill for months now due to the fact that no team has made a significant offer for the Trail Blazers to consider.
It has been hard for other teams to offer assets for the All-NBA player due to the fact that Lillard has his heart set on Miami.
NBA Rumors: Damian Lillard's threats against anyone but the Heat trading for him still stand
Most likely, the Heat are playing hardball for the player due to the fact that their actual offers are so low. Additionally, the Heat do not necessarily have the right assets to make a trade. Most likely, the trade will include Tyler Herro in a deal. Herro does not fit with Scoot Henderson at all on the offensive or defensive end.
With this in mind, the Heat have been looking to add a third team to a deal in order to get it done. The Nets have reportedly been approached and willing as a third team but don't seem to want to give up draft picks for the player.
This doesn't even consider the fact that the Trail Blazers are looking to move Jusuf Nurkic in any deal. At this point with all of the drama surrounding it, it's hard to see a world where the Blazers are able to get off Nurkic's deal and still get draft picks.
As the NBA season turns into focus things will start to be extremely toxic between the two sides. If Lillard is still in a Trail Blazers uniform as training camp comes, the chances that he pulls off a Jimmy Butler becomes ever more likely. If Portland doesn't trade him by then and he throws a fit, it becomes extremely hard for any team not named Miami to make a move.
At that point, Miami might end up lowballing even more. If Lillard causes a problem in training camp or elsewhere in the season, things will get extremely ugly for the Trail Blazers.
While it was a couple of years ago and Butler was heading into free agency, the Timberwolves got practically nothing for the superstar when they traded him. While the pick compensation might still be large, this could be a return that the Trailblazers end up getting if they go down this road.