Damian Lillard fits the win-now timeline
While trading away multiple assets is never an easy thing for a team to do, it is easier when there is a clear path to title contention. For Miami, there is a clear path as acquiring Damian Lillard would put them right on par with the other teams in the Eastern Conference.
If the series against the Milwaukee Bucks proved anything it is that the Heat are one offensive difference-making superstar away from really being contenders.
With Lillard on the team, they would be able to compete with Milwaukee and the Brooklyn Nets when it comes to star power. An argument could be made that they would also leapfrog the Philadelphia 76ers in the process.
Players such as Herro and Achiuwa could develop down the road, but Miami does not have time to find out as long as Butler is a part of their core. He puts the team in a win-now position and if they are going to take full advantage of that, they need to flip some of their younger assets into established products.
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Lillard fits the win-now timeline the Heat are on and would be a perfect fit for a new version of the Big 3 in Miami.