Grade the Trade: Heat land Damian Lillard; Tyler Herro gets fresh start in wild pitch

Could the Milwaukee Bucks explore the possibility of trading Damian Lillard to the Miami Heat this offseason?
Miami Heat v Milwaukee Bucks
Miami Heat v Milwaukee Bucks / Stacy Revere/GettyImages
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Grading a wild trade proposal that would have the Miami Heat landing Damian Lillard this summer with Tyler Herro getting a fresh start with the Milwaukee Bucks.

As the Milwaukee Bucks prepare for a very important NBA playoff run, there are some very big questions surrounding the team after an underwhelming regular season. One of the biggest revolves around whether the offseason gamble for Damian Lillard will end up paying off when it matters most. In the regular season, the Lillard experience left much to be desired. The hope is that will change in the postseason.

However, if it doesn't, it could lead to some big questions heading into the offseason.

Should the Milwaukee Bucks consider trading Damian Lillard this offseason?

On his ESPN show First Take, Stephen A. Smith birthed the idea of the Bucks possibly exploring a Lillard trade this offseason if they have a disappointing end to their season, stating that Lillard is not happy in Milwaukee. Whether that's true or not remains to be seen but if the Bucks do lose in the first or second round, trading Lillard wouldn't be a terrible idea.

Less than two months ago, Lillard admitted that he wasn't fully comfortable in the Bucks offense just yet. While some of that could be attributed to the mid-season head-coaching change, you can't help but wonder if there could be other variables also involved. If the Bucks do have a disappointing end to their season, it wouldn't be outlandish to pull the plug on the Lillard experience. And retooling the team via trade could be an offseason resolution.

If that's an idea the Bucks want to explore, there may not be another trade partner out there that makes more sense than the Miami Heat. In one bold and crazy offseason proposal, there's a pathway toward the Heat and Bucks both coming out as winners.