A Damian Lillard trade seems inevitable after the Portland Trail Blazers took Scoot Henderson with the No. 2 pick in the 2023 NBA Draft, and ESPN has an idea for a deal with the Miami Heat. In this trade, Lillard goes to South Beach for a package centered around Tyler Herro. So, let’s grade this hypothetical trade between the Blazers and Heat.

ESPN's hypothetical Tyler Herro for Damian Lillard trade

With a Damian Lillard trade looking more likely after the Blazers drafted Scoot Henderson with the No. 2 pick instead of dealing it for a veteran, ESPN’s Nick Friedell offers this hypothetical trade for Portland’s seven-time All-Star:

Miami Heat get:
Damian Lillard

Portland Trail Blazers get:
Tyler Herro
Duncan Robinson
Nikola Jovic
Draft rights to Jaime Jaquez Jr. (No. 18, 2023)
2028 first-round pick
2029 pick swap
2030 first-round pick

Heat grade

For the Heat, the team gets a core of Lillard, Jimmy Butler, and Bam Adebayo to improve the top end of the roster and stay competitors in the Eastern Conference. With that Big 3, the Heat has as much top talent as any team on that side of the league and would become a nightmare in a playoff series. Plus, they don’t give up any of their major 2023 playoff contributors like Gabe Vincent, Caleb Martin, Max Strus, or Kevin Love (although they still have to re-sign all but Martin).

The downside here is that the team is giving up the 23-year-old Herro and replacing him with the soon-to-be 33-year-old Lillard. Adding that to Butler, who turns 34 in September, gives the Heat an older core.

Plus, the team got rave reviews for drafting Jaime Jaquez Jr. from UCLA, who is an excellent fit with the Heat due to his diverse skill set.

In the end, when you weigh the pluses and minuses, adding Lillard to Butler and Adebayo is a risk worth taking. It’s a bold move that is reminiscent of the Heat trading for Shaquille O’Neal or signing LeBron James and Chris Bosh, and those audacious plays ended in championships.

Heat trade grade: A-

Blazers grade

This Damian Lillard trade for the Blazers also seems like a good move and possibly the best the team can do. In a post-Rudy Gobert trade world, an organization must get multiple young players and picks for a superstar, or the deal will seem wildly underwhelming to fans.

With this hypothetical trade, the Blazers acquire a budding star and legit 20-point-per-game scorer in Tyler Herro, who is best suited as the second or (even better) third-best player on a contending team. That’s exactly what he’ll be in Portland with Scoot Henderson, Shaedon Sharpe, and Anfernee Simons already on the roster.

The team also puts more shooting around Henderson, which is always a smart move. Duncan Robinson is an excellent specialist and Nikola Jovic is an intriguing young offensive-minded big who can shoot from distance. And he’s just 20, which is two years younger than the rookie Jaquez.

Portland would still need a rim-protecting bog to round out their squad, but the 3-and-D potential of Jaquez on the wing is a solid pickup, too.

As for the picks, those are interesting as well. They don’t start until 2028, which means that if Butler and Lillard are still even in the league at that point, they’ll be 39 and 38, respectively, the season prior.

That means that these hypothetical picks could hypothetically be quite high in the draft if unprotected. Even the pick swap could be valuable if Miami is on its way down and Portland is ascending in six years. The caveat to that is, when was the last time the Heat were bottoming out? The team is so good at reloading on the fly, the last time they picked in the single digits was back in 2008 (No. 2, Malik Beasley), and before that, it was grabbing Dwyane Wade at No. 3 in 2003.

Blazers general manager Joe Cronin has been on the job for less than two years at this point, but if this Damian Lillard trade doesn’t immediately pay dividends, he may not be around for the second half of the deal when the picks come good in 2028 and beyond.

Still, the picks will become trade assets sooner than that, and Cronin can use them to add talent to the roster as soon as the upcoming trade deadline, depending on what the immediate results of the move are.

Ultimately, this is a win-win trade for both sides, and the young players and picks to start the Blazers’ rebuild around Henderson are about as good as the team can hope to do.

Blazers trade grade: A